The Best Vineyard & Winery Wedding Venues in Chester, MD

The Best Vineyard & Winery Wedding Venues in Chester, MD

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13 Wedding Venues in Chester, MD

Vineyards, wineries
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Castle Farm 

5.0

Snow Hill, MD
  • Up to 500 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $24,999

Castle Farm is a private, exclusive 150-acre premier equestrian estate & wedding and corporate event venue located in Snow Hill, on the beautiful Eastern Shore of Maryland. We are an authentic historic farm, breeding elegant Andalusian horses and adorable micro mini Scottish Highland cows. The barn is an immaculate timber-framed barn with hammered copper walls and the solid mahogany barn doors provide the perfect entrance to your fairytale. If you want an authentic barn wedding, where your guests will make lasting memories for years to come, taking photos with newborn foals, and being impressed with impeccable service AND a truly magical experience for your wedding, book Castle Farm today.

Why you'll love this venue

  • Accommodates more than 200 guests
  • Pets can join the celebration
  • Provides a dedicated team on-site

Venue considerations

  • Not for you if you don't want a rustic vibe
  • Best for events with big guest lists
Awarded Best of Zola
We have been working with [and for] Castle Farm since the beginning. We did the first wedding ever there! Every year they add something new and there are tons of places for pictures! The owners are great people and are extremely accommodating to everyone! You can have a beer pony, horses in your portraits and the guests truly love the interaction! No matter where you are you get an incredible view! I can't say enough about this place and the owners...it is definitely a one of a kind location you won't forget!
Andrew Nock Photography, 10 months ago
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District Winery 

5.0

Washington, DC
  • Up to 200 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $25,000

District Winery hosts full-service weddings for up to 200 guests. The first working winery in Washington, DC, District Winery is located in Navy Yard along the Anacostia River. Our modern, sophisticated, waterfront wedding venue with floor to ceiling windows, an outdoor terrace, and sweeping river views is the ideal venue for your wedding. District Winery include our highly regarded wedding cuisine and wines made onsite. Executive Chef Christian Fischhuber brings years of international culinary expertise to our venue, as he oversees every detail of your menu. Couples work with a District Winery event manager who will assist with all of the details, from helping curate the perfect menu to coordinating with vendors to ensure seamless execution. All District Winery weddings are turnkey and include the use of our custom walnut tables, chairs, high top tables, bar stools, marble topped bars, china, glassware, flatware, linen napkins, printed menus, table top items to enhance your decor.

Why you'll love this venue

  • Full catering menu to choose from
  • Allows pets
  • Has a dance floor for celebration

Venue considerations

  • No on-premises lodging options
  • No built-in audiovisual options
  • Best for events with big guest lists
Awarded Best of Zola
We had both our ceremony and reception at the District Winery in early December. When we went to visit the winery, we both loved how unique the space was compared with other venues. It was not the traditional ballroom, high ceilings, chandeliers, rounds with tablecloths to the ground. It was warm, inviting, and rustic. Kat, our event manager, was assigned to us to execute our wedding. It was beyond helpful to have someone from the venue to assist. As the event got closer there were so many decisions to make, but Kat helped tremendously. One example was food - bride’s dad really wanted pasta, but it was not an option on the food menu. Kat discussed with the chef and made it a possibility. Although we did not end up adding pasta, the chef made a special plate for the bride’s dad (he was the only one who really wanted the pasta). Overall, we had a great experience from the bride and groom perspective, but also many of our guests commented on how nice of a venue and the quality of the food.
Amanda D., 2 months ago
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Bohemia Overlook 

5.0

North East, MD
  • Up to 300 guests
  • Select services
  • Indoor & outdoor
  • Starts at $5,000
  • Offer

Experience the perfect combination of luxury and timeless charm at Bohemia Overlook, a breathtaking estate nestled along the peaceful shores of the Elk River. With over 80 acres of picturesque landscapes and a refined old-money, country-club vibe, our property offers the elegance and sophistication that create an unforgettable wedding day. Choose from three stunning venues— The Manor, The Beach, and The Barn—to bring your vision to life. What Makes Bohemia Overlook Unique? 🌿 Stunning Venue Options: Whether you prefer the rustic elegance of The Barn, the classic charm of The Manor, or the relaxed luxury of The Beach, we have a space that fits your style perfectly. 🍷 A Full-Day Celebration: Enjoy early access to the venue, giving you the freedom to relax, prepare, and celebrate without feeling rushed. Our dedicated team is here to help you create a day that celebrates your love story in style and sophistication.

Why you'll love this venue

  • Has a dance floor for celebration
  • Dressing room available
  • Multiple event spaces

Venue considerations

  • Not wheelchair accessible
  • Does not provide event staff
  • No on-premises lodging options
The moment I saw Bohemia Overlook, I knew it was the Wedding venue for us. The Venue is affordable and offers a good amount of accommodations that other venues do not and would cost extra even. The little things do matter, it adds up as we all know. The Venue kept in great contact with me and responded to me right away with questions I had through the whole experience and worked with me. Such a beautiful Venue. Was nervous when I found out a new owner took over, but realized quickly I didn’t need to be. The new owners kept up with the same pace of communication and response time and even on our Wedding day they greeted us and made sure everything was going good. We even got a beautiful view of the water on the hill for some wedding photos. My Wife and I enjoy coming here for different events and the wine room when it’s open. This place will forever be a cherished memory and not everyone can say that they can go back to where they got married. So much more to say about this place, but without going on a rant, just know this place is amazing. To even include how beautiful the barn looks upstairs at night, wasn’t expecting that since we usually see it during the day.
Talia C., a month ago
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La Banque de Fleuve 

5.0

Havre De Grace, MD
  • Up to 200 guests
  • Raw space
  • Indoor & outdoor

La Banque de Fleuve presents two distinct spaces, each with its own unique allure. The Historic Bank, with its lofty ceilings, ornate chandeliers, and intricate details, exudes the timeless opulence of a bygone era, where elegance beautifully intersects with history, creating an atmosphere that whisks you away to another time. On the other hand, the Seaplane Base offers a contrasting yet equally enchanting setting. Nestled alongside the river's edge, it provides sweeping panoramic views of the water, infusing your celebration with a natural serenity. With its open-air design and the soothing sounds of the water in the background, it becomes a tranquil oasis right in the heart of the city.

Why you'll love this venue

  • Multiple event spaces
  • Versatile for various event styles
  • Both indoor and outdoor options

Venue considerations

  • Dance floor not included
  • Best for events with big guest lists
  • Not wheelchair accessible
Awarded Best of Zola
Our day was perfect because of the outstanding staff and the care given to this venue! The venue is gorgeous uand our guests raved about how classy the location was and the gorgeous views of our day. Kim checked in with our families throughout and the day to make sure our expectations were met and to alleviate and concerns or potential stressors. If you are looking for a quaint town to have your wedding, you must check out this hidden gem! It is a venue that will have you loving your big day and all the photo opportunities! They are an inclusive venue and never made us feel uncomfortable as an LGBT couple.
Leslie & S., a year ago
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Pinstripes North Bethesda 

5.0

North Bethesda, MD
  • Up to 500 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $2,000

Whether you are hosting a wedding reception, ceremony, bridal shower or bachelor(ette) party our dynamic ballrooms and private event spaces provide an upscale yet relaxed space for your special day. We host truly unique events and deliver sophisticated fun through combining our from-scratch Italian-America menu with the classic games of bowling and bocce ball. Let our talented event team work with you on a customized event to suit your personal style and help you bring your dream wedding to life to create a perfect day that you and all your guests will be sure to remember!

Why you'll love this venue

  • Multiple event spaces
  • All-inclusive venue packages
  • Rustic-chic setting

Venue considerations

  • Not wheelchair accessible
  • On-site parking not available
  • Does not allow pets
We LOVED working with Melanie and the Pinstripes team. They truly made our dreams become a reality. They helped make our day extremely special. Melanie is such a fabulous communicator and is extremely organized. She is amazing!
Kelsey H., 7 months ago
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Two Lions Vineyards 
Upper Marlboro, MD
  • Up to 120 guests
  • Select services
  • Indoor & outdoor
  • Starts at $6,900

Nestled amidst rolling vineyards and picturesque landscapes, our venue offers an enchanting backdrop for your special day. Whether you envision an intimate ceremony with close family and friends or a grand affair with all the bells and whistles, our dedicated team is committed to crafting a wedding experience tailored to your dreams. From exchanging vows under the open sky to dancing the night away in our elegant event spaces, every moment at Two Lions Vineyards is infused with romance and charm.

Why you'll love this venue

  • Has a chic vibe
  • Flexible event spaces
  • Provides catering services

Venue considerations

  • Does not allow pets
  • Not wheelchair accessible
  • On-site parking not available
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Robin Hill Farm and Vineyards 
Brandywine, MD
  • Up to 200 guests
  • Select services
  • Indoor & outdoor
  • Starts at $5,500

Robin Hill Farm and Vineyards offers a rustic yet elegant setting for weddings, surrounded by lush vineyards and scenic countryside. The venue's charming farmhouse and expansive grounds provide a picturesque backdrop for both ceremonies and receptions. With personalized service and attention to detail, Robin Hill Farm ensures a memorable celebration. Ideal for couples seeking a tranquil and natural environment, this venue captures the essence of rustic charm and sophistication.

Why you'll love this venue

  • Flexible event spaces
  • Bridal suite on site
  • Surrounded by beautiful vineyards

Venue considerations

  • Does not allow pets
  • Not for you if you prefer a more modern aesthetic
  • Couple must handle cleanup and setup

Location flexible? Discover venues near Chester, MD

About wedding venues in Chester, MD

How much do wedding venues typically cost in Chester, MD?

The cost of a wedding venue varies widely by location, number of guests, and many other details of the wedding package. Chester, MD offers a range of options that can fit most budgets. Raw venue space rentals (which only include the space itself) start at $250 and average $4,000. All-inclusive packages start at $1,000 and average $8,300.

What types of venues can I find in Chester, MD?

Chester offers a wide range of venues, including Beach and waterfront, Historic estate and Barn and ranch.

What are some of the best wedding and reception venues available in Chester, MD?

Some of the most popular venues in this area include The Wylder Hotel, Black Walnut Point Inn and Chesapeake Bay Beach Club. But just like finding "the one," finding the perfect wedding venue takes time and a little bit of magic. Start by envisioning your dream wedding - the ambiance, style, and location. Then, explore our extensive collection of carefully curated wedding venues. Our marketplace provides detailed information, stunning photos, and real couples' reviews to help you make an informed decision. Trust your instincts, and when you find that venue that gives you butterflies, you'll know it's the one.

What questions should I ask when booking a venue in Chester, MD?

It all depends on what you're looking for, but you may want to consider things like whether the venue has an on-site bridal suite (73% in Chester do) or whether the venue provides an event coordinator (48% in Chester do!).

Additionally, some venues work with certain caterers and require a minimum food and beverage spend in addition to the space rentals. Others might have a recommended list of preferred caterers that they'd like you to work with.

Can the venues in Chester, MD accommodate both small and large weddings?

Of course! Small wedding venues in Chester, MD can host intimate parties while large venues can accommodate up to 600. The average venue in Chester can seat 200 guests.

What amenities do the reception venues in Chester, MD offer?

The venues in Chester, MD are known for the exceptional suite of services and amenities offered to couples and their wedding parties. The most common services provided are Wi-Fi, Dressing room / Bridal Suite and On-site accommodations. Some venues even offer Transportation!

What types of wedding venues are in Chester, MD?

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