The Best On-Site Accommodations Wedding Venues in Woolford, MD

The Best On-Site Accommodations Wedding Venues in Woolford, MD

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43 Wedding Venues in Woolford, MD

On-site accommodations
Quick responder
The Anchorage1800 

5.0

Trappe, MD
  • Up to 100 guests
  • Raw space
  • Outdoor
  • Starts at $6,000

The Anchorage, with origins back to 1800, is a venue set on 12 private acres with waterfront views situated on the beautiful Choptank River. We offer a relaxed, peaceful and romantic experience on the shores of the river, which is part of the Chesapeake Bay waterway. The venue includes an open air, covered pavilion with spectacular waterfront views for up to 100 people.

Why you'll love this venue

  • Provides a dedicated team on-site
  • Caters to out-of-town guests
  • Surrounded by nature

Venue considerations

  • Not wheelchair accessible
  • Does not have a dance floor
  • Couple must handle cleanup and setup
The Anchorage was amazing! My wife and I got married here last June, and to say everything was perfect would be an understatement. It's hard to put into words explaining how great Woody and Michelle were helping us make our special day go exactly as planned. The property is beautiful, spacious, and well kept. The waterfront view was the perfect backdrop for our ceremony (Woody even went out of his way to make an aisle of sand for us to walk down). The cigar shack was awesome and the barn was also set up for me and my groomsmen to get ready and hang out until the big moment (they especially enjoyed the darts, ring and hook, and bar with a kegerator). My family and I were very happy with the rooms which were spotless, comfortable, and included refrigerators/kitchenettes. My wife was very happy with her space to get ready, especially with Michelle doing everything she could ensuring the girls had what they needed and making sure everyone was stress free! Woody and Michelle were more than accommodating. Breakfast was always delicious (the smoothies and Woodys Waffles were my favorites). They were also life savers dealing with our vendors dropping stuff off (at times earlier than expected), even using their golf cart to help move stuff down to the beach to help set up. The golf cart also came in handy taxing people up and down the hill when needed! I HIGHLY recommend this venue! Woody and Michelle are two of the most kind, accommodating (and hilarious) people I've ever met, and I can't begin to thank them enough for everything they did to make sure our special day went off without a hitch. We fully intend on coming back to enjoy their beautiful BnB again!
Daniel N., a year ago
Quick responder
The Wylder Hotel 

5.0

Tilghman, MD
  • Up to 200 guests
  • All-inclusive
  • Indoor & outdoor

We are a place where you can express your unique vision and bring your wedding dreams to life. There are a few different ways to celebrate your wedding weekend here at Wylder. Depending on headcount and date availability. From intimate waterfront escapes to extravagant weekend-long festivities, we have the perfect package for you! We have over 9 acres of lush grounds, 50 hotel rooms, 1100 feet of private waterfront & over 4,000 sq. feet of indoor & outdoor waterfront flexible event space for you to plan the custom wedding of your dreams! * Hotel rooms are booked by your guests *

Why you'll love this venue

  • Promotes a party atmosphere
  • All-inclusive venue packages
  • Pets can join the celebration

Venue considerations

  • No on-site bridal suite
  • Not wheelchair accessible
  • Lighting and sound are not included
The Wylder Hotel was an excellent choice for our wedding venue. Their communication throughout the planning process was efficient, friendly, and organized, which helped make the experience stress-free. The quality of their work and overall value was exceptional - the venue was beautifully decorated, they were flexible in accommodating our needs, and their pricing was budget-friendly. The food they provided was phenomenal, and the overall organization of our special day was effortless. A special shoutout to KD, who was amazing in helping us bring our vision to life. We highly recommend The Wylder Hotel to any couple looking for a clean, flexible, and beautiful wedding venue.
Jennifer H., 22 days ago
Quick responder
Herrington on the Bay 

5.0

North Beach, MD
  • Up to 250 guests
  • All-inclusive
  • Outdoor & indoor
  • Starts at $10,000

For over 30 years, Herrington on the Bay has transformed waterfront dreams into unforgettable wedding realities. We know you'll be captivated by our panoramic Chesapeake Bay views and our delectable, locally-sourced menus. But what truly sets us apart is the unparalleled service we deliver. When you choose Herrington's full-service wedding package, we take care of everything: the venue, planning and coordination, exquisite food and beverage service, attentive staff, and stunning on-site amenities. We'll also collaborate with you to craft a customized menu featuring sustainable ingredients from our trusted partner farms. Let Herrington on the Bay orchestrate your luxurious waterfront wedding, a celebration as exquisite and unforgettable as your love story.

Why you'll love this venue

  • Provides catering services
  • Multiple event spaces
  • Offers convenient lodging options

Venue considerations

  • Limited cleanup and setup services
  • Not for you if you are looking for something nontraditional
  • Not wheelchair accessible
Herrington on the Bay has everything you need for your special day! Amazing views, food, private space, options, AND the most accommodating and gracious team! I toured several other venues and there was no denying we would not have received the same service or experience anywhere else! From the moment you walk in, Herrington on the Bay changes the wedding game process and experience!
Michelle Y., a month ago
Roselynn Manor 

5.0

Aquasco, MD
  • Up to 80 guests
  • Raw space
  • Outdoor & indoor
  • Starts at $3,000

Originally named St.Mary's Rectory this property was inducted into the National Register of Historic Places in 1987 and remains true to it's original mid-19th-Century appearance.Nestled in the quiet corners of Aquasco,MD. Roselynn Manor is the perfect destination for your dream event. Boasting 5 acres the property is rich in legacy dating back to 1849 making it a cherished landmark into ur community.

Why you'll love this venue

  • Both indoor and outdoor options
  • Raw space for complete customization
  • Rustic charm with elegance

Venue considerations

  • Does not provide event staff
  • No in-house catering options
  • Lighting and sound are not included
Classic venue with timeless appeal, beautiful interiors, impeccable service and spacious grounds made the most perfect event venue for us. The warms atmosphere makes it wonderful for any occasion. 10/10!
Jessica, 8 months ago
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Hyatt Place Kent Narrows & Marina 

4.0

Grasonville, MD
  • Up to 150 guests
  • All-inclusive
  • Outdoor & indoor
  • Starts at $69

Immerse yourself in unmatched elegance and charm at the Queen Anne Event Center, nestled within the breathtaking Hyatt Place Kent Narrows & Marina, where every detail is thoughtfully curated to surpass expectations and create enduring memories against the backdrop of stunning waterfront vistas. Elevate your next gathering, wedding, or conference with our versatile 4,000 square feet of indoor meeting and event space, perfectly suited for both professional and social gatherings. Step outside onto our 3,000 square feet of additional patio space, offering picturesque views that enhance any outdoor event. Whether accommodating up to 150 guests in our expansive Queen Anne Ballroom or hosting intimate gatherings in our stylish Meeting Room or the Narrows Boardroom, our venue is designed to meet your every need.

Why you'll love this venue

  • Provides lighting and sound
  • Classic seating dinner
  • All-inclusive venue packages

Venue considerations

  • Not for you if you are drawn to more unconventional venues
  • Not wheelchair accessible
  • No free parking
We had a wonderful experience working with the Hyatt Place Kent Narrows & Marina for our wedding. Their communication was a bit spotty early on, but they really stepped up their game as our date got closer and were very responsive and attentive. The venue itself was perfect for the size of our wedding - it had just the right amount of space and the views of the water were beautiful. On the day of, the service was fantastic and the staff went above and beyond to make sure we and our guests were comfortable and taken care of. We were very pleased with the overall value and quality of this venue.
Khadijah, 2 months ago
Quick responder
Kent Island Resort 

4.0

Stevensville, MD
  • Up to 275 guests
  • All-inclusive
  • Outdoor & indoor
  • Starts at $6,000

Situated on Maryland’s Eastern Shore, Kent Island Resort welcomes guests with a historic manor house and sprawling countryside, perfect for landmark celebrations. Tailored wedding packages, three elegant venues, celebrated chefs, and a dedicated team ensure unforgettable moments—whether it’s an intimate affair or a grand celebration. The Resort boasts exclusivity, modern sophistication, waterfront views, boating activities, hiking trails, cycling, and luxurious onsite amenities. Located just an hour from Washington, D.C., Kent Island Resort offers outstanding service and memorable experiences.

Why you'll love this venue

  • Allows pets
  • Historic touches
  • All-inclusive venue packages

Venue considerations

  • Large venue, not ideal for small guest lists
  • Dance floor not included
  • On-site parking not available
From start to finish, the team at Kent Island Resort was incredibly responsive and organized, ensuring our wedding day went smoothly. Mackenzie was there to answer any questions we had throughout the entire process, and we felt heard and understood when it came to bringing our vision to life. The simple elegance and beauty of the venue were exactly what we were looking for, and the Kent Island Resort team executed it perfectly!! We could not have asked for anything more from this wonderful team - our wedding day was truly magical thanks to their hard work and attention to detail.
Carlie D., a year ago
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Chesapeake Bay Beach Club 

4.9

Stevensville, MD
  • Up to 310 guests
  • All-inclusive
  • Indoor & outdoor

If you’re visiting this page, chances are you’re planning the most important day of your life! First off, please accept a resounding congratulations from the entire team at Chesapeake Bay Beach Club. For over two decades, we’ve been journeying alongside couples and their families as they plan for this joyous occasion, and we’d be bluffing if we said it wasn’t our absolute favorite thing in the world! A stunning, coastal Maryland backdrop ideal for your dream wedding, we cordially invite you to plan your very special day with us at Chesapeake Bay Beach Club! With four fantastic venue options to choose from (each of which brings its own unique distinction), the custom-curated, Chesapeake Bay wedding of your dreams is within reach like never before! Select from our array of remarkable spaces as you plan not only your wedding ceremony, but also your splendid rehearsal dinner, celebratory reception, cheery bridal luncheon, and more!

Why you'll love this venue

  • Provides event staff
  • Has a dance floor for celebration
  • Multiple event spaces

Venue considerations

  • No in-house lighting and sound packages available
  • Not for you if you are drawn to more unconventional venues
  • Not wheelchair accessible
Awarded Best of Zola
We got married at Chesapeake Bay Beach Club on May 17, 2025, and had the most stellar experience we could have hoped for. From the very beginning, we were blown away. We attended one of their Saturday open houses for our initial tour and were immediately impressed - not just by the stunning waterfront venue and all the flexible, thoughtfully designed event spaces, but also by how knowledgeable, professional, and confident the entire team was. We left that tour knowing we’d be in the best hands and we were absolutely right. Every step of the planning process was seamless - from the delicious food and drink tasting, to room blocks at their on-site inn, to spa services, to vendor coordination and final timeline planning. Everything was organized, stress-free, and incredibly well executed. Samantha, our coordinator, was truly a rockstar. She answered every one of my many (many!) questions with patience and clarity, and always helped ease any nerves I had in the weeks leading up to our wedding day. Her responsiveness and calm presence made all the difference. The wedding day went absolutely flawlessly. Everything ran like clockwork. I didn’t have to worry about a single thing—every vendor knew where to go and when to be there, and all the details we’d planned came together perfectly. I truly got to just show up and have the best day of my life. The team at CBBC knows what they’re doing, and I cannot recommend them highly enough. If you're looking for a venue that combines stunning views with expert-level coordination and service, look no further.
Alexis W., 6 months ago
Quick responder
Hemlock Farm 

5.0

Edgewater, MD
  • Up to 125 guests
  • Raw space
  • Outdoor
  • Starts at $3,200

Hemlock Farm is the perfect rustic venue for a beautiful summer wedding. Known for its stunning weddings and annual Christmas tree selection, this charming farm offers a warm and welcoming atmosphere. Weddings take place in front of the picturesque red barn, surrounded by family and close friends. Hemlock Farm also offers the freshest fir Christmas trees and greenery, making it a family-friendly destination year-round. Celebrate your special day in a setting that combines rustic charm with heartfelt hospitality at Hemlock Farm.

Why you'll love this venue

  • Raw space for complete customization
  • Has a relaxed and casual vibe
  • Rustic-chic setting

Venue considerations

  • No in-house catering options
  • Limited cleanup and setup services
  • Not wheelchair accessible
Hemlock Farm was absolutely amazing for our wedding day! The communication from Jennifer was quick, fast, and incredibly kind and reliable throughout the entire process. Jennifer was prompt in responding to all of our questions and even allowed us to arrive on the property early for set up and allowed our rental companies to pick up their rentals by Monday. For how many days of use you get out of the space along with the value we received was simply unbeatable - the venue and grounds were absolutely beautiful and exceeded our expectations in every way. We couldn't have asked for a better place to celebrate our special day. Our entire family (both sides) loved the venue and kept commenting on it throughout the weekend and after! I highly recommend Hemlock Farm to any couple looking for an incredible wedding experience!
Evangeline H., 6 months ago
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Marcellus Farms 

5.0

Brandywine, MD
  • Up to 150 guests
  • Select services
  • Indoor & outdoor
  • Starts at $2,499

Host your next unforgettable event at Marcellus Farms™, where elegance meets nature. Whether you envision a grand gathering in Manor En Noire, a rustic yet refined celebration in our Luxe Barns, or an open-air experience with our Outdoor Rentals, we offer versatile spaces tailored to your needs. From intimate gatherings to large-scale events, our estate provides the perfect setting for weddings, corporate retreats, and special occasions. Book your venue today and bring your vision to life!

Why you'll love this venue

  • Feels like a getaway
  • Flexible event spaces
  • Bridal suite on site

Venue considerations

  • Not for you if you're looking for a sleek and contemporary space
  • On-site parking not available
  • No built-in audiovisual options
Marcellus Farms was a true gem of a wedding venue for our special day. From the moment we first reached out, the staff was friendly, pleasant, and agreeable in their communication, putting us at ease throughout the planning process. When we had to move our event indoors due to unexpected rain, the team at Marcellus Farms seamlessly transitioned our celebration to an inviting indoor space that lasted comfortably through the night. The quality of their work and attention to detail was truly exceptional, and we are so grateful to have found such a rare and special place to host our wedding.
Wayne H., 2 months ago
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Doubletree by Hilton Annapolis 

5.0

Annapolis, MD
  • Up to 300 guests
  • All-inclusive
  • Indoor

DoubleTree by Hilton Hotel Annapolis is a premier hotel located in Annapolis, Maryland. The stylish hotel features all the modern furnishings, decor, and amenities needed to plan and host the most wonderful wedding celebration. From ceremonies, receptions, engagement parties, and more, the hotel provides a range of event spaces that can be transformed to create the wedding couples have always envisioned. Couples have the choice of two stunning and elegant ballrooms both including spacious pre-function areas to choose from. The large Coastal Ballroom and the Mainsail Ballroom are both open-plan event spaces can be configured in a variety of ways and styled to best suit each couple’s preferred design and atmosphere. The Coastal Ballroom can accommodate 120 guests and up to 300 guests in the Mainsail Ballroom.

Why you'll love this venue

  • Wheelchair accessible
  • Multiple event spaces
  • Has a fun and festive vibe

Venue considerations

  • Venue feels large for events with small guest lists
  • No built-in audiovisual options
First, I want to extend another thank you to you, Allison, the event staff, catering staff, front desk staff and everyone else who helped make our event memorable. No ask was too big or too small, and during the event, everyone was gracious and willing to assist and suggest last minute changes. We especially wanted to thank Nelson and his team and Rae, our bartender!
Connie, 21 days ago
Inn At Osprey Point 

5.0

Rock Hall, MD
  • Up to 220 guests
  • Select services
  • Indoor & outdoor
  • Starts at $12,000

The Inn at Osprey Point is a sprawling estate in the charming village of Rock Hall, Maryland. This premier wedding venue and B&B is surrounded by 30 acres of lush landscapes and spectacular water views. It offers a variety of beautiful settings for any wedding day. The colonial-style inn caters to intimate celebrations while a one-of-a-kind waterfront tented reception will charm guests and loved ones. Whatever classic coastal vision couples have for their special day, the Inn at Osprey Point can make dream weddings come true. Please reach out for the full wedding package including food and bar choices that are available. With catering, bar, a full staff, and day-of coordination, your wedding is bound to be stress-free with Osprey Point!

Why you'll love this venue

  • Provides setup and cleanup
  • Multiple event spaces
  • Pets can join the celebration

Venue considerations

  • Does not have a dance floor
  • No built-in audiovisual options
  • Best for events with big guest lists
We had our dream wedding at Osprey Point in June of this year. The event coordinator is so responsive and easy to work with. She truly made our day so perfect and special and we couldn't be more thankful for everyone's hard work at Osprey Point. Thank you!
Kay W., 2 years ago
White Vine Venue 

5.0

Riverdale, MD
  • Up to 120 guests
  • Raw space
  • Indoor

Celebrate life’s most meaningful moments at White Vine Venue — a stylish, all-inclusive space designed for baby showers, birthday parties, bridal parties, graduations, and all your intimate gatherings.

Why you'll love this venue

  • Provides setup and cleanup
  • Has onsite accommodations
  • Provides lighting and sound

Venue considerations

  • No all-inclusive dining options
  • Does not have a dance floor
This event space offered a stunning ambiance with its modern decor and versatile layout, easily accommodating our needs. The staff were incredibly helpful and attentive, ensuring every detail was handled with professionalism. Overall, it provided an exceptional experience and a beautiful backdrop for a memorable occasion.
Klyle Y., 7 months ago
The Westin Alexandria 

5.0

Alexandria, VA
  • Up to 450 guests
  • Raw space
  • Indoor & outdoor
  • Starts at $22,207

Edison Ballroom, our largest venue, is an exquisite backdrop with column lights and gold chandeliers Take advantage of our Hopkins Foyer and Pre-Function Area for your lively cocktail hour Our Wedding Specialists will ensure your dreamlike reception is flawlessly planned and executed Work with our culinary staff to create a personalized dining experience that pleases your palate With our cutting-edge AV equipment, bring wedding toasts, slideshow and entertainment to life Receive exclusive rates on your Alexandria Old Town happily-ever-after with our group reservations

Why you'll love this venue

  • Pets can join the celebration
  • Handles all cleanup logistics
  • Has onsite accommodations

Venue considerations

  • Not for you if you are looking for something nontraditional
  • On-site parking not available
  • Venue feels large for events with small guest lists
We worked closely with Laure (as did my Mom...) and she was incredible. Patient, quick to respond, positive, and made me so confident that all things related to our reception would go smoothly. I did not envision getting married in a hotel, but Laure and the team at the Westin made us SO glad we hosted our reception there!
Catherine C., 4 years ago
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Swan Cove Manor 
Cambridge, MD
  • Up to 200 guests
  • Select services
  • Outdoor

Swan Cove Manor is a 5 house waterfront estate on the eastern shore of Maryland. We host 3 night weekend celebration and can accomadate up to 70 people. We include a lot in our wedding package with additionals services that can be offered. Swan Cove Manor is your private waterfront estate for a spectacular wedding weekend on the Eastern Shore. Situated on 20+ scenic acres, this "one of a kind" property offers unspoiled natural elegance against the stunning backdrop of the Chesapeake coast. Couples can celebrate for an entire weekend, utilizing five spacious, designer-furnished manor homes for lodging and preparation. Imagine your ceremony on the waterfront followed by a grand reception tailored to your unique vision, from casual to formal.

Why you'll love this venue

  • Caters to out-of-town guests
  • Dressing room available
  • Has a relaxed and casual vibe

Venue considerations

  • No in-house lighting and sound packages available
  • Best for events with big guest lists
  • No free parking
Quick responder
Black Walnut Point Inn 
Tilghman, MD
  • Up to 500 guests
  • All-inclusive
  • Outdoor

We're a blank slate and host weekend weddings, so estimates given are for Friday - Sunday morning. We also have 15 years experience and know how to help with all the details. Our point is surrounded by miles of water, with sunrise over the Choptank River and sunset over the Chesapeake Bay. We have no neighbors, no cut-off times, and we customize our weddings using our local vendors. We have no hidden fees. We set up meetings with your vendors and you pay them directly. Because we have one of the most unique locations, we had hosted some of the most unique weddings guests have ever attended. The privacy of our point ensures the freedom to make your day as special as you are as a couple. And with plenty of time, there is no rush enjoying the point with your friends and family.

Why you'll love this venue

  • Wheelchair accessible
  • Private area for the wedding party
  • Has a relaxed and casual vibe

Venue considerations

  • No in-house lighting and sound packages available
  • No all-inclusive dining options
  • Additional event staff required
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The Oaks 
Easton, MD
  • Up to 250 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $75,000

Say “I Do” on Maryland’s Eastern Shore. The setting is magical and entirely yours. The Oaks and its grounds become a private preserve for you, your wedding party, and your guests. It’s all yours on the evening before, the day of, and the morning after your waterfront wedding. The meticulously landscaped grounds of our waterfront wedding venue in Maryland offer a wide variety of outdoor activities in a relaxing setting. The wedding celebration itself becomes part of enduring memories, tailored just to accommodate your preferences… and how you’ve always dreamed your wedding should be.

Why you'll love this venue

  • All-inclusive venue packages
  • Provides catering services
  • Provides event staff

Venue considerations

  • Large venue, not ideal for small guest lists
  • On-site parking not available
  • Not wheelchair accessible
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Rod 'N' Reel Resort 
Chesapeake Beach, MD
  • Up to 300 guests
  • All-inclusive
  • Outdoor & indoor
  • Starts at $10,000

Nestled in the charming bayside town of Chesapeake Beach, MD, the Rod N’ Reel Resort blends contemporary coastal elegance with effortless convenience. This waterfront retreat offers a perfect backdrop for your celebration, featuring luxurious beachside venues and modern ballrooms designed to feel anything but traditional. From onsite accommodations to an array of dining experiences and late-night indulgences, your guests will enjoy comfort, style, and entertainment all in one place. To make your vision a reality, the Rod N’ Reel Resort provides wedding amenities, from onsite catering to bar service by our culinary team. Our dedicated wedding specialists are here to guide you every step of the way—from crafting timelines and floor plans to providing seamless support on your wedding day! Quietly tucked along the Western Shore of the Chesapeake Bay, the resort feels like a serene destination getaway—yet it’s less than an hour from Washington, D.C. and Baltimore.

Why you'll love this venue

  • Private area for the wedding party
  • Has onsite accommodations
  • Provides event staff

Venue considerations

  • Not wheelchair accessible
  • No in-house lighting and sound packages available
  • No free parking
Quick responder
The River House at Queenstown Harbor 
Queenstown, MD
  • Up to 125 guests
  • All-inclusive
  • Outdoor & indoor
  • Starts at $13,000

Celebrate your special day at the River House at Queenstown Harbor, a picturesque waterfront wedding venue with stunning views and personalized service. Craft unforgettable memories with customized wedding packages to bring your vision to life.

Why you'll love this venue

  • Offers convenient lodging options
  • All-inclusive venue packages
  • Flexible event spaces

Venue considerations

  • Does not allow pets
  • No in-house lighting and sound packages available
Buddy's Crabs & Ribs 
Annapolis, MD
  • Up to 300 guests
  • All-inclusive
  • Indoor
  • Starts at $2,000

Nestled in the heart of historic Downtown Annapolis, Buddy’s has been a cornerstone of local dining for years. Perched on the second floor of the iconic 1909 Aaron Lee Goodman building, our restaurant combines history, charm, and unbeatable views of the Inner Harbor. We’re known for our fresh, flavorful, and family-friendly menu that has something for everyone. Whether you're cracking into Buddy’s Crabs by the dozen, savoring our fall-off-the-bone ribs, or enjoying oysters on the half shell, your taste buds are in for a treat.

Why you'll love this venue

  • Provides a dedicated team on-site
  • Provides lighting and sound
  • Has a dance floor for celebration

Venue considerations

  • Does not allow pets
  • Not wheelchair accessible
  • Venue feels large for events with small guest lists
The Historic Inns of Annapolis 
Annapolis, MD
  • Up to 200 guests
  • Select services
  • Indoor & outdoor
  • Starts at $12,000

Picture your dream day by the waterfront along the Chesapeake Bay at our award-winning Annapolis wedding venues. Our indoor and outdoor spaces are perfect for intimate ceremonies and receptions. Choose from multiple venues across three charming inns and find the right space to match your theme and style. We offer full-service catering to satisfy any taste, with dishes inspired by the rich history of Annapolis. If you're planning a military wedding, we're moments from the Naval Academy in Annapolis, making arrival seamless and convenient. Our professional planners will help attend to every detail, from audio-visual support to helping you pick the perfect package. Our three historic inns offer a unique blend of Victorian character and modern amenities, making them the perfect place to relax and explore all Annapolis offers. Just steps from the Maryland State House and the United States Naval Academy, our inns are within walking distance of all the city's attractions.

Why you'll love this venue

  • Historic touches
  • Provides setup and cleanup
  • Provides event staff

Venue considerations

  • No in-house lighting and sound packages available
  • Does not have a dance floor
  • Not wheelchair accessible
Quick responder
Hilton Garden Inn Annapolis Downtown 
Annapolis, MD
  • Up to 70 guests
  • Select services
  • Indoor
  • Starts at $1,000

Nestled in the heart of historic downtown Annapolis, Hilton Garden Inn Annapolis Downtown offers a charming and convenient setting for weddings and celebrations. Located at 174 West Street, this stylish hotel combines comfortable guest accommodations with flexible event space — ideal for couples who want a downtown venue with onsite lodging and hospitality services.

Why you'll love this venue

  • Offers convenient lodging options
  • Allows pets
  • Wheelchair accessible

Venue considerations

  • Dance floor not included
  • No free parking
  • No in-house lighting and sound packages available
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Venue 54 
Delmar, MD
  • Up to 220 guests
  • Indoor & outdoor
  • Starts at $3,500

Welcome to Venue 54, Delmar, Maryland’s premier wedding and event venue. Our weekend rental includes overnight accommodations at Bungalow 54, ensuring a relaxed and seamless celebration for you and your guests.

Why you'll love this venue

  • Rustic-chic setting
  • Has a fun and festive vibe
  • Accommodates more than 200 guests

Venue considerations

  • Does not have a dance floor
  • No in-house catering options
  • Does not provide event staff
The Brandon Estate 
Parsonsburg, MD
  • Up to 600 guests
  • Select services
  • Outdoor & indoor
  • Starts at $15,000

Founded in 2003, the gated-entry Brandon Estate is a cherished and prized estate of the Brandon Family. An Fierm, which translates to “The Farm” in Irish, was originally a smaller four bedroom house, primarily used as a getaway cabin and romantic escape. Over the years, the Brandons added over 3000 square feet of living space and amenities including a great room, a stone wood-burning fireplace, a wine cellar, a pool, a game room, and a private balcony overlooking the estate. The mansion is now well over 5000 square feet- comprised of 6 bedrooms, 7 bathrooms, and a stunning designer kitchen. All in all, the mansion can sleep 16 people comfortably. With over 300 acres of private farm land, 200 acres of which is farmed crop. Loaded with scenic walking trails, barns, fresh water fish-stocked ponds, canoes, a stone chapel, and rolling landscape- the property is sure to keep you busy during your stay!

Why you'll love this venue

  • Allows pets
  • Caters to out-of-town guests
  • Has a dance floor to dance the night away

Venue considerations

  • Large venue, not ideal for small guest lists
  • Not wheelchair accessible
  • Not for you if you prefer a more modern aesthetic

Location flexible? Discover venues near Woolford, MD

About wedding venues in Woolford, MD

Maryland offers exceptional variety for couples planning their special day. You can choose from Chesapeake Bay's waterfront settings with their shimmering views, explore Baltimore's historic mansions filled with ornate architectural details, or celebrate in Eastern Shore's rustic barns surrounded by pastoral landscapes that create a picturesque backdrop for your celebration.

What's the True Cost of a Maryland Wedding?

The price tag for Maryland weddings varies significantly based on guest count. Small gatherings of about 50 guests average $22,754 while mid-sized celebrations with 150 guests typically run around $51,712. Large weddings hosting 300 guests can reach $89,329. Your venue will likely be your biggest expense at about $8,532 for a typical wedding; that's 16% of your total budget for a 150-person celebration, so choosing wisely matters.

Which Maryland Regions Offer the Best Wedding Settings?

# Baltimore Area

Baltimore venues showcase the area's rich architectural heritage and stunning harbor views. The Belvedere features incredible gilded ceilings crystal chandeliers and grand staircases that create perfect dramatic entrances for your big moment. Celebrations at the Bay gives you panoramic waterfront ceremony spaces with dedicated sunset photography locations that'll make your album spectacular. You'll appreciate their customizable reception layouts that comfortably fit up to 250 guests so everyone has space to enjoy.

# Eastern Shore

The Chesapeake Bay region delivers quintessential Maryland beauty that your guests will remember. Chesapeake Bay Beach Club offers private beaches for your ceremony waterfront ballrooms with floor-to-ceiling windows and charming oyster shell pathways that reflect the local maritime culture. Castle Farm combines beautiful equestrian elements with thoughtful accessible design including solid-surface walkways and convenient golf cart shuttles so all your guests can participate fully.

How Much Should You Budget for Wedding Services in Maryland?

For a 150-guest wedding in Maryland, expect these costs:

ServiceAverage CostPercentage of Total
Venue$8,53216%
Catering$6,82613%
Florals$6,54113%
Bar Service$5,46111%
Photography$4,9069%
Videography$3,9118%
Wedding Planner$4,0538%
Band/DJ$1,7503%
Cake/Desserts$1,4013%
Hair/Makeup$7902%

When Should You Book Your Maryland Venue?

Most couples in Maryland secure their venues about 14 months before their wedding date. You'll want to plan ahead since December sees the highest inquiry volume when many newly engaged couples start their search. Keep in mind that summer and fall wedding dates often come with premium pricing, so if you're flexible with your date you might find better value in other seasons.

Where Can You Find Accessible Wedding Venues in Maryland?

Castle Farm Weddings offers truly inclusive spaces for all your guests. You'll find accessible ceremony and reception areas with no steps wheelchair-friendly walkways designated handicapped parking and ADA-compliant restrooms throughout. Ten Point Acres Venue can comfortably seat up to 500 guests with fully accessible facilities including large handicap restrooms and climate control for year-round comfort so everyone can focus on celebrating your special day.

What Are Maryland's Best Venues for Remote Participation?

Chesapeake Bay Beach Club provides stunning waterfront settings that enhance the virtual experience for guests who can't attend in person. You'll love their post-event storytelling approach that keeps remote guests feeling connected. Graduate Annapolis gives you advanced tech infrastructure for high-quality streaming with nautical-themed digital backdrops that help engage virtual viewers and make them feel part of your celebration.

Which Maryland Venues Feature Outstanding Culinary Experiences?

Valley Country Club set in a grand 1850s mansion offers all-inclusive packages with elegant butlered hors d'oeuvres and complete meal service that impresses even the most discerning guests. Their crab cakes are simply phenomenal and often receive rave reviews from attendees long after the event. You'll benefit from their over 70 years of hosting expertise that ensures everything from appetizers to dessert flows seamlessly.

Maryland offers exceptional variety for couples planning their special day. You can choose from Chesapeake Bay's waterfront settings with their shimmering views, explore Baltimore's historic mansions filled with ornate architectural details, or celebrate in Eastern Shore's rustic barns surrounded by pastoral landscapes that create a picturesque backdrop for your celebration.

What's the True Cost of a Maryland Wedding?

The price tag for Maryland weddings varies significantly based on guest count. Small gatherings of about 50 guests average $22,754 while mid-sized celebrations with 150 guests typically run around $51,712. Large weddings hosting 300 guests can reach $89,329. Your venue will likely be your biggest expense at about $8,532 for a typical wedding; that's 16% of your total budget for a 150-person celebration, so choosing wisely matters.

Which Maryland Regions Offer the Best Wedding Settings?

# Baltimore Area

Baltimore venues showcase the area's rich architectural heritage and stunning harbor views. The Belvedere features incredible gilded ceilings crystal chandeliers and grand staircases that create perfect dramatic entrances for your big moment. Celebrations at the Bay gives you panoramic waterfront ceremony spaces with dedicated sunset photography locations that'll make your album spectacular. You'll appreciate their customizable reception layouts that comfortably fit up to 250 guests so everyone has space to enjoy.

# Eastern Shore

The Chesapeake Bay region delivers quintessential Maryland beauty that your guests will remember. Chesapeake Bay Beach Club offers private beaches for your ceremony waterfront ballrooms with floor-to-ceiling windows and charming oyster shell pathways that reflect the local maritime culture. Castle Farm combines beautiful equestrian elements with thoughtful accessible design including solid-surface walkways and convenient golf cart shuttles so all your guests can participate fully.

How Much Should You Budget for Wedding Services in Maryland?

For a 150-guest wedding in Maryland, expect these costs:

ServiceAverage CostPercentage of Total
Venue$8,53216%
Catering$6,82613%
Florals$6,54113%
Bar Service$5,46111%
Photography$4,9069%
Videography$3,9118%
Wedding Planner$4,0538%
Band/DJ$1,7503%
Cake/Desserts$1,4013%
Hair/Makeup$7902%

When Should You Book Your Maryland Venue?

Most couples in Maryland secure their venues about 14 months before their wedding date. You'll want to plan ahead since December sees the highest inquiry volume when many newly engaged couples start their search. Keep in mind that summer and fall wedding dates often come with premium pricing, so if you're flexible with your date you might find better value in other seasons.

Where Can You Find Accessible Wedding Venues in Maryland?

Castle Farm Weddings offers truly inclusive spaces for all your guests. You'll find accessible ceremony and reception areas with no steps wheelchair-friendly walkways designated handicapped parking and ADA-compliant restrooms throughout. Ten Point Acres Venue can comfortably seat up to 500 guests with fully accessible facilities including large handicap restrooms and climate control for year-round comfort so everyone can focus on celebrating your special day.

What Are Maryland's Best Venues for Remote Participation?

Chesapeake Bay Beach Club provides stunning waterfront settings that enhance the virtual experience for guests who can't attend in person. You'll love their post-event storytelling approach that keeps remote guests feeling connected. Graduate Annapolis gives you advanced tech infrastructure for high-quality streaming with nautical-themed digital backdrops that help engage virtual viewers and make them feel part of your celebration.

Which Maryland Venues Feature Outstanding Culinary Experiences?

Valley Country Club set in a grand 1850s mansion offers all-inclusive packages with elegant butlered hors d'oeuvres and complete meal service that impresses even the most discerning guests. Their crab cakes are simply phenomenal and often receive rave reviews from attendees long after the event. You'll benefit from their over 70 years of hosting expertise that ensures everything from appetizers to dessert flows seamlessly.

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