The Best Retreat Wedding Venues in Chester, MA

The Best Retreat Wedding Venues in Chester, MA

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13 Wedding Venues in Chester, MA

Lodges, retreats
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Union Station Banquets 

5.0

Northampton, MA
  • Up to 200 guests
  • Select services
  • Indoor
  • Starts at $7,000

We are Northampton's newest, most modernized banquet facility, however Union Station has been a fixture for over 100 years. Originally built in 1897, Union Station pairs history and modernization, with our premiere 200 seat ballroom, three restaurants, and adjoining ancillary spaces such as The Atrium, The Lounge, and The Blue Goose. We host an array of events that are just as unique as we are! Weddings, rehearsal dinners, parties, corporate events, and more.

Why you'll love this venue

  • Caters to out-of-town guests
  • Wheelchair accessible
  • Has a dance floor to dance the night away

Venue considerations

  • Not for you if you are looking for something nontraditional
  • Best for events with big guest lists
  • No built-in audiovisual options
Awarded Best of Zola
We had the best wedding at Union Station, and it was all thanks to Neil and his team. Before the wedding, he would always respond to my emails and questions, and was very accommodating with what we wanted. Anything we threw at him, he would make it work. He has such a calm presence, too, which is VERY needed on your wedding day! Robert was our personal right-hand man to me and my husband on our wedding day, and he was amazing!! He made sure we had time to ourselves amongst the chaos of the evening, he made sure we ate our delicious dinner, and he even helped me with my train and veil during pictures and bustled my dress before the reception!! Rehearsal and decor pickups were super stress-free and easy too. Thank you to everyone at Union Station for making our wedding the best day of our lives (so far)!!!
Eva C., 2 years ago
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The Barn At Montague Retreat Center 

5.0

Montague, MA
  • Up to 200 guests
  • Select services
  • Indoor & outdoor
  • Starts at $6,000

Welcome! We are so glad you are considering the Montague Retreat Center for hosting your wedding! Our team wishes to help personalize your experience in our extraordinary place. Our lush Ceremony Circle, nestled up to the apple orchard, sits beneath one of the oldest maple groves in Massachusetts, with a stunning view across the valley. Our Stone Patio features a permanent 40’ x 50’ reception tent and a 75’ long retaining wall/bench. Our elegant, rustic Great Hall barn has chestnut beams, bamboo floors, lots of glass and geothermal cooling. Visit our website to learn more about our rich history! Montague couples will work with our exclusive catering team, Wheelhouse for food & bar. Some of our other amenities include 10 on-site accommodations that sleep between 24-32, our yurt, an ADA-compliant lift, and accessible restrooms. Two streams run through the property and the Robert Frost Trail is within walking distance.

Why you'll love this venue

  • Dressing room available
  • Has a dance floor to dance the night away
  • Provides event staff

Venue considerations

  • Venue feels large for events with small guest lists
  • Not for you if you're looking for a sleek and contemporary space
  • Does not allow pets
As a wedding photographer, I'm always thrilled when I get an inquiry for a wedding at the Montague Retreat. It's one of my all time favorite places to photograph. Their team is highly experienced and very thoughtful. I know I can rely on them with any help I may need. The landscapes are dreamy, and the reception hall is beautiful. The long dirt road that leads to the retreat makes for beautiful New England portraits, and the view from the hill at sunset is unforgettable. 10/10 would highly recommend the Montague Retreat Center. I'd love to get married there!
Stephanie Craig, 4 years ago
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Inn at Mount Pleasant 

5.0

Torrington, CT
  • Up to 250 guests
  • Select services
  • Indoor & outdoor
  • Starts at $9,200

Welcome to the Inn at Mount Pleasant! We have a barn for a rustic wedding, an inn for 10 guests, and beautiful New England views. We offer numerous scenic ceremony locations, a firepit, bistro lighting and chandeliers, farm tables, and much more!

Why you'll love this venue

  • Space for a large guest list
  • Offers convenient lodging options
  • Bridal suite on site

Venue considerations

  • Not for you if you're looking for a sleek and contemporary space
  • Does not provide event staff
  • Couple must handle cleanup and setup
Nestled in the Torrington valley, this unique venue is one of our favorites. This careful maintained and expertly run facility offers the best of indoor venues with the great outdoors all in one location. Always a pleasure working with the owners and the event planning team of EngagedCT. Well organized and extremely professional.
engagedct@gmail.com, 3 years ago
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Stablegate Farm & Vineyard 

5.0

Castleton On Hudson, NY
  • Up to 200 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $14,500

From the minute you arrive at Upstate New York’s finest farm and vineyard venue, you will be enamored by the historic charm and rustic elegance that defines Stablegate Farm and Vineyard. Fall in love with the 19th-century Stablegate Barn filled with charming antique decor and ambient market-street lighting. For more intimate gatherings, our Stablegate Lodge provides guests with a warm, inviting atmosphere to celebrate. Choose from a private vineyard, a hilltop view of the Catskill mountains, a 200-year-old Dutch barn door, or a fossil stone fireplace for your Upstate New York ceremony.

Why you'll love this venue

  • Pets can join the celebration
  • Rustic yet refined style
  • Multiple event spaces

Venue considerations

  • No on-site guest accommodations
  • Large venue, not ideal for small guest lists
  • On-site parking not available
I don’t even know where to begin. At the beginning of our wedding journey, finding a venue was the hardest thing we could’ve done. My husband and I had a specific vision in mind and had an incredibly difficult time finding a place that we loved that was also within our budget. We’re from the LI area but knew we wished to get married upstate. We must have visited at least 10 venues. Then on our way home from one, my husband found Stablegate on a whim. We looked everything over and it had the barn that I wanted, and the catering included that my husband wanted and I said “if we visit and we like it, I’m putting a deposit down the next day.” And that’s exactly what we did. Birch Hill is an incredible family owned company with so many aspects attached to it, it was hard not to fall in the second we saw it. Over 2.5 years, I never once regretted that decision and once the wedding day came and went I knew it was the right choice for us. The food is amazing and a ton of different options (including catering to my vegan guests), the staff are incredible, and the vibes are immaculate. Our wedding coordinator Jared was really the star of the show. He was super accommodating to all of our needs, organized, and just all in all a ridiculously sweet and funny guy. When our wedding day ended up getting rained out, he came up with backup plans right on the spot that honestly fit our vibe so much more than our original plan and I really truly have Jared to thank for that. Jared treated us like we were old friends that he was just helping throughout the day. He is someone I will truly forever be the most grateful for to have on my wedding day. I have heard so many horror stories about venues, and I can honestly say this is not one of them. Stablegate Barn and the Birch Hill Catering Company have my highest recommendation. And if you need a coordinator, ask for Jared. Really truly from the bottom of my heart, thank you for an amazing wedding day.
Ariella P., 2 months ago
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Vanderbilt Lakeside Bar Room & Guesthouse 

5.0

Hudson, NY
  • Up to 130 guests
  • Select services
  • Indoor & outdoor
  • Starts at $7,000

Vanderbilt Lakeside offers thoughtfully curated stays and events in a welcoming gathering space, with custom in-house food and bar packages. Charming, versatile, and ideal for group getaways, retreats, and celebrations of all sizes—from intimate dinner parties, to large scale gatherings and bespoke weddings. ​ The space itself is a newly redesigned, large (6000 SF) house. It was originally built in the 1800s. The outdoor areas can also be incorporated for your event--our deck and yard are completely open-air; you would be welcome to work with a third-party rental company to have a tent set up, if of interest. Including the outdoor areas, we have the following approximate Capacity for Events: *Seated Dinner with a Ceremony: 100 guests *Seated Dinner without a Ceremony (or with a ceremony that has fewer guests in attendance): 130 *Cocktail Party with or without a Ceremony: up to 150 guests

Why you'll love this venue

  • Provides lighting and sound
  • Both indoor and outdoor options
  • Full catering menu to choose from

Venue considerations

  • No free parking
  • No on-site bridal suite
  • Not wheelchair accessible
I photographed a wedding here in the spring and I really really hope to come back! I can't say enough great things about the venue, the staff, and the planner. If you're looking for a unique venue, you've found it! Do you want your wedding day to go smoothly? Have it here!!! As a photographer this venue was pure eye candy and gave me so many interesting spots for photos!
Tara, 5 months ago
Farm Road Estate 

5.0

West Dover, VT
  • Up to 300 guests
  • All-inclusive
  • Indoor & outdoor

Imagine twinkling lights, farm-to-table fare, and your closest friends gathered under the expansive Vermont Sky. Farm Road Estate is the quintessential Vermont wedding destination uniquely suited to host weekend-long wedding celebrations and large events. Located in West Dover, VT near the base of Mount Snow, this stunning property is spread across 32acres, an easy drive from anywhere in New England. Farm Road Estate offers a variety of locations for all your wedding needs. We offer numerous ceremony locations: Beside the picturesque ponds, on the beautiful 1450 sqft bluestone terrace, or in our enchanted forest. Our newly renovated Great Room - once an 18th century sawmill - features exposed beams, wood floors, elegant chandeliers, and a large fireplace provides incredible ambiance for an indoor reception. We can also host up to 300 guests outdoors! Accommodations on-site for up to 96 guests! Come see why Forbes listed this property as one of the most romantic Inns in the world.

Why you'll love this venue

  • All-inclusive venue packages
  • Rustic-chic setting
  • Has a dance floor for celebration

Venue considerations

  • Not for you if you don't want a rustic vibe
  • Large venue, not ideal for small guest lists
Farm Road was incredible from the moment we first emailed about our wedding. Not only are the services, food and grounds INCREDIBLE- the people that work there too. Everything was perfect even more beautiful than we imagined. Our guests could not stop raving about the delicious food and gorgeous property. It truly felt like the best adult summer camp that we never wanted to leave. Taylor, the coordinator at Farm Road, was especially wonderful in ensuring we felt ready for the big day and taken care of. We couldn't have done it without her.
Nikki J., 5 months ago
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Bellavista Country Estate 
Old Chatham, NY
  • Up to 200 guests
  • Select services
  • Outdoor
  • Starts at $5,000

Your wedding at Bellavista Country Estate will include a two night or longer stay at the beautiful estate for up to 16 guests. The property is located on 60 private acres in picturesque Hudson Valley. Amenities include more than 1,000 square feet of beautiful bridal & groom men’s suites that are perfect for photo ops, game room with air hockey, pinball, card table, in-house gym, library, five full bathrooms, library and more .. all for the wedding couple, family and friends to enjoy during their stay.

Why you'll love this venue

  • Rustic yet refined style
  • Surrounded by nature
  • Provides event staff

Venue considerations

  • Requires outside catering services
  • No built-in audiovisual options
  • Best for events with big guest lists

Location flexible? Discover venues near Chester, MA

About wedding venues in Chester, MA

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

The cost of a wedding venue varies widely by location, number of guests, and many other details of the wedding package. Chester, MA offers a range of options that can fit most budgets. All-inclusive packages start at $500 and average $6,600.

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

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

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

Some of the most popular venues in this area include Quonquont Farm, The Boylston Rooms and The Log Cabin. 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, MA?

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 (80% in Chester do) or whether the venue provides an event coordinator (75% 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, MA accommodate both small and large weddings?

Of course! Small wedding venues in Chester, MA can host intimate parties while large venues can accommodate up to 500. The average venue in Chester can seat 150 guests.

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

The venues in Chester, MA are known for the exceptional suite of services and amenities offered to couples and their wedding parties. The most common services provided are Wheelchair accessible, Wi-Fi and Bar services. Some venues even offer Transportation!

What types of wedding venues are in Chester, MA?

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