The Best Small Wedding Venues in Chester, NY

The Best Small Wedding Venues in Chester, NY

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11 Wedding Venues in Chester, NY

Up to 50 guests
Available on September 13, 2026
Quick responder
City Winery Hudson Valley 

5.0

Montgomery, NY
  • Up to 350 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $30,000

Thank you for considering City Winery for your upcoming wedding. City Winery offers the romance and unique style of a rustic winery wedding with the ease of a full-service wedding venue, located on the outskirts of the small village of Montgomery, NY, surrounded by the sights and sounds of the Wallkill River with the Shawangunk Mountains in the distance, and near numerous art and architecture attractions like the Storm King Art Center, Dia Beacon, and Bannerman Castle. With the ability to host everything from a small intimate rehearsal dinner to an elaborate wedding for up to 350 guests, our goal is to help you create everlasting memories. We look forward to bringing your wedding vision to life!

Why you'll love this venue

  • Provides lighting and sound
  • Provides event staff
  • Provides setup and cleanup

Venue considerations

  • Large venue, not ideal for small guest lists
Awarded Best of Zola
Our daughter and son-in-law had their wedding at City Winery Hudson Valley a few weeks ago and we are thrilled with our entire experience! We worked with Lerika from the very beginning when we first toured as our Sales Manager and communications with her throughout the process were perfect. Lerika also worked extremely well with our planner (Lauren F. from Wild Blooms – recommended by CW) and the two of them made sure all details were perfect. When we first toured CW, we loved all the different spaces and, due to a rainy wedding day, were very grateful for the many options. Although we intended for the ceremony to be by the river, the indoor space was beautiful and provided the perfect backdrop made even more beautiful with white flowers that popped against the brick and windows. And having cocktail hour within the bar area and restaurant, which they closed for us, made our event very private and allowed for sufficient seating during that time. The buttlered hors d’oeuvres were plentiful and the stations constantly replenished so they always looked stocked. Service was incredible throughout the day and our guests appeared to be served dinner all at once, and wait staff were very attentive. There were never lines at the bar during cocktail hour or the reception which was helped by the table wine service. We chose the Steak Bavette for our beef entrée and I was concerned the 6 oz standard portion would be too small so we upgraded to 8 oz which ended up being huge! And all the food served throughout the day was delicious! Lerika was attentive throughout the wedding day as was Tiffany, the CW event coordinator, who we did not meet until that day. Lerika and Tiffany anticipated our needs and made sure we were all taken care of throughout the day. Security identified a potential issue with one of our guests who had too much to drink and discreetly and professionally addressed it without our even knowing about it. We had more than 160 guests in attendance and the space was big enough to ensure it was easy to move around the tables while still feeling intimate. I love that we were able to place only two rows of tables on each side of the dance floor so everyone was close to the activity and never far apart. Our guests danced throughout the wedding which made it very fun. With recommendations from CW, we selected a florist (Laruen P. from Wild Blooms) and bistro lighting from Fox Haus that transformed the space and made it so beautiful. All the photos are absolutely gorgeous even though most were taken indoors. We also reserved the boiler bar for the guys to get ready which was fun for them and the Nest for the ladies which was spacious and beautiful. And lastly, we hosted an afterparty in the boiler bar for the friends of the bride and groom which was perfect to give them extra time with their close friends! CW hosts a combined food tasting for all couples with scheduled weddings and it gave us a great glimpse of what the actual wedding day would be like with plenty of special and personal touches for the bride and groom. I cannot say enough about how wonderful our experience was, and we continue to receive so many compliments from our guests! It was fun, it was beautiful, it was delicious, it was perfectly what our daughter and son-in-law envisioned!
Marie P., a month ago
Quick responder
The Wedding Foundry Hudson Valley 

5.0

Highland, NY
  • Up to 75 guests
  • All-inclusive
  • Outdoor
  • Starts at $15,000

We include coordination and staff, photography, officiant, florals, catering, desserts and more. Say "I do" to a stress-free wedding experience with The Wedding Foundry. Let us handle the details while you focus on what truly matters – celebrating your love in a setting that's as unique and unforgettable as your relationship. We host perfect Micro Weddings up to 75 guests.

Why you'll love this venue

  • Provides lighting and sound
  • Allows pets
  • Exudes old-world charm

Venue considerations

  • Not for you if you don't want a rustic vibe
Awarded Best of Zola
Billiam, Erica and their entire team were amazing! The whole process was smooth and they were always able and willing to answer any of our questions, we had lots of them! The end result of our wedding was incredible. I was blown away at the beauty of the venue and the food was incredible. My guests were all amazed at how gorgeous everything was and couldn’t get over how delicious the food was. They are still talking about it! I can’t wait to see the photos Erica took, she was great to work with and made us feel comfortable during the whole process! I recommend this venue to everyone! Thank you to everyone at Liberty View Farm for making our day perfect! It was truly a fairytale wedding.
Samantha B., 5 days ago
Quick responder
Mountainville Manor 

5.0

Mountainville, NY
  • Up to 150 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $15,000

Mountainville Manor ensures that your wedding day is a merging of natural beauty and award winning, world class cuisine. The Victorian details and beautiful grounds offer a timeless backdrop for your special day, where you can say your vows in front of the charming gazebo. There is also an inside ceremony option, in our ballroom. Cocktail hour is enjoyed in the “home” part of the Manor with access to the wrap around porch and courtyard area with fire pit. The Manor provides two areas for a spectacular reception - an elegant setting with windows on several sides of the main ballroom to accommodate up to 150 guests or a tented reception on our lush landscaped grounds accommodating up to 250 guests. You may arrive four hours before your ceremony and get ready in our spacious bridal party suites. Hosting only one wedding a day, we pay special care and attention to every detail, making the wedding planning process stress-free and the event flawless for you and your guests.

Why you'll love this venue

  • Has a dance floor to dance the night away
  • Versatile for various event styles
  • All-inclusive venue packages

Venue considerations

  • Not for you if you are looking for something nontraditional
  • No on-site guest accommodations
I cannot day enough good things about Mountainville manor. We had an elopement ceremony and pictures on the property. We could not have been happier and luckier to have found this venue. The whole process was simple and although it was an elopement with just the two of us, the owner Lauren, made it feel so special. The bouquet that was included in the elopement package was beautiful and exceeded my expectations. The grounds are immaculately kept w beautiful landscaping. The newly remodeled interior is as beautiful. There is a beautiful bridal and grooms room. The bride room includes a full bathroom w a shower. The owner, Lauren was very attentive and made sure we had water and a bite to eat as well as offering to go to the store in the event we forgot something. She was extremely accommodating and and made sure our vision was executed and really wanted to make sure we had the wedding of our dreams.
Gabriella and R., 4 years ago
Sugarhouse 
Chester, NY
  • Up to 350 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $15,000

Located in Hudson Valley, this 1854 Stone House Farm offers a beautiful, rustic setting for enchanting weddings & events. We love hosting a dream wedding but it’s not all we do! Wow your guests with delicious catering and scenery to pair with any event: showers, holiday parties, birthdays, company events, reunions, or any reason to gather and party. SugarHouse offers on and off site catering for any occasion.

Why you'll love this venue

  • Multiple event spaces
  • All-inclusive venue packages
  • Provides catering services

Venue considerations

  • Not for you if you're looking for a sleek and contemporary space
  • Not wheelchair accessible
  • No on-site guest accommodations
Stagecoach Inn 

5.0

Goshen, NY
  • Up to 200 guests
  • All-inclusive
  • Indoor & outdoor

From the moment you step into our historic inn, you can see why so many couples envision their wedding here. From rehearsal dinners to lavish wedding ceremonies, intimate receptions, bridal showers or day after wedding brunch with family and friends, we do it all and cater to every detail. The inn’s owner, Faith Ferguson, is a renowned wedding and event planner, so your special occasion is truly in expert hands. Faith is known for her attention to detail which is evident throughout the Inn. The Stagecoach Inn staff will be on hand to help you with all of the personal touches that will make the most of your special day. Please be sure to schedule a visit to the Stagecoach Inn early into your wedding planning so that we may show you our historic inn, introduce you to our team, and discuss your wishes further.

Why you'll love this venue

  • Both indoor and outdoor options
  • Provides event staff
  • Full catering menu to choose from

Venue considerations

  • No built-in audiovisual options
  • Does not allow pets
  • Not wheelchair accessible
Still riding the high from our wedding weekend! We were absolutely floored by all the work Jen and Ally and the whole Stagecoach team did to make our wedding weekend spectacular! They have several different packages that you can choose from which allowed us to find something that truly worked for us. We ended up having around 115 guests for the wedding and the space was just perfect! We had been to the Inn for dinner before and we knew we wanted to make food a priority. Chef Jerrel hit it out of the park for the rehearsal dinner, the cocktail hour/reception, and the brunch the next morning! Also because they have rooms upstairs, we were able to have our closest family stay and not have to worry about any travel! We couldn't recommend them enough!
Michelle G., 10 months ago
Quick responder
Blooming Hill Farm 

5.0

Monroe, NY
  • Up to 200 guests
  • All-inclusive
  • Indoor & outdoor

Blooming Hill Farm is a rustic wedding venue located in New York's Hudson Valley. This family-owned farm is known for growing organic produce on land in Blooming Grove for over 30 years. They use their own fresh ingredients to give you and your guests a true farm-to-table experience. Their friendly staff will work closely with you to coordinate decor, timelines, vendors, etc. Its beautiful natural setting and fresh cuisine make for a wedding your guests won't soon to forget.

Why you'll love this venue

  • Rustic charm with elegance
  • Handles all cleanup logistics
  • Flexible event spaces

Venue considerations

  • Large venue, not ideal for small guest lists
  • No dedicated areas for getting ready
  • Not for you if you're looking for a sleek and contemporary space
Blooming Hill Farm was an absolute dream to work with for our wedding day. From the very first interaction, their communication style was thorough, attentive and easy - Kate gave me her personal cell number and was available to answer any questions I had almost immediately in the days leading up to our big day. The farm was absolutely breathtaking, with the venue's natural beauty and lush landscaping providing the perfect backdrop for our special celebration. Our guests could not stop talking about how good the food was and everyone said it was the best wedding they have ever been to. The staff was so amazing, making sure to think about everything possible in advance to ensure our wedding day went off without a hitch. We can’t wait to come back to the restaurant on our anniversary! We are so grateful to the entire Blooming Hill Farm team for helping to make our day truly unforgettable.
Brittany K., 8 months ago
The Orange Inn Boutique Hotel 
Goshen, NY
  • Up to 86 guests
  • All-inclusive
  • Indoor
  • Starts at $2,000

Nestled in the small New York town of Goshen, the Limoncello at The Orange Inn offers a charming setting for an upstate style wedding. Surrounded by gently rolling hills, this picturesque Inn has been a long-time fixture in this charming town -- making it the ideal location for a memorable occasion. Featuring three private dining rooms, an expansive patio, and a full bar, this Inn provides soon-to-be-wed couples with an intimate yet elegant location for hosting their wedding day. Imagine toasting to your future as spouses over a finely set table, enjoying an expansive spread of magnificent cuisine that has been tailored to suit your exact tastes and preferences.

Why you'll love this venue

  • Provides catering services
  • Dressing room available
  • All-inclusive venue packages

Venue considerations

  • Dance floor not included
  • Does not allow pets
  • Not wheelchair accessible
Harness Racing Museum & Hall of Fame 
Goshen, NY
  • Up to 120 guests
  • Select services
  • Indoor & outdoor
  • Starts at $1,500

The Harness Racing Museum & Hall of Fame is housed in a magnificent Tudor-style stable, built in 1913. The unique setting of this historic site is beautiful, elegant and comfortable with an atmosphere to suit all tastes. It is the perfect place to plan your Wedding Ceremony and/or Reception. The museum is located in the historic downtown Goshen, New York. Its elegant and timeless Haughton Hall can accommodate up to 125 guests. For larger groups our beautifully manicured lawn and garden provide a perfect stage for a country wedding celebration! Whether you are planning a traditional or non-traditional affair, our staff at The Harness Racing Museum & Hall of Fame will ensure your special day is memorable.

Why you'll love this venue

  • Provides catering services
  • Classic seating dinner
  • Flexible event spaces

Venue considerations

  • No on-premises lodging options
  • No in-house lighting and sound packages available
  • Not for you if you are looking for something nontraditional
The Captain’s Table 
Monroe, NY
  • Up to 100 guests
  • All-inclusive
  • Indoor & outdoor
  • Starts at $1,050

Ensure that your next party or work event is a great success by hiring The Captain’s Table to prepare the food! We offer both in-house private dining and off-site catering available. We have dozens of dishes for you to choose from with ½ trays and full trays available. Depending on the nature of your event, different types of foods may be more appropriate than others. Certain trays will be ideal for a buffet-style feast while others are intended to be enjoyed as hors devours with drinks for a casual affair. Great for After Wedding Celebrations!

Why you'll love this venue

  • Both indoor and outdoor options
  • Provides event staff
  • Provides catering services

Venue considerations

  • No on-site bridal suite
  • No on-premises lodging options
  • Does not allow pets
Emmerich Tree Farm 
Warwick, NY
  • Up to 160 guests
  • Select services
  • Outdoor

Emmerich Tree Farm is a working Christmas Tree Farm catering to the 'Choose-and-Cut' market in Warwick, NY, just 50 miles NW of the George Washington Bridge. Our property has been in the family since 1960, and the trees were planted in 2007. Our pavilion is 30 by 40 and was built in the summer of 2011 using beams harvested from the property. There are rustic accents added throughout, which help make the space unique. Articulating glass windows & doors on the South & East walls allow us to control temperature shifts, creating a unique indoor/outdoor space. Adjacent to the pavilion is a tented patio which is 60' x 30'. The tent is provided by our venue, includes hanging string lights, and has sides available upon request. The space allows room to seat up to 180 people using rectangular tables and up to 130 people using 5' round tables. We also have a Bridal tent built with rustic cedar trim. The tent is furnished with seating, full-length mirror and power.

Why you'll love this venue

  • Picturesque garden backdrop
  • Provides lighting and sound
  • Provides event staff

Venue considerations

  • Does not allow pets
  • On-site parking not available
  • Not wheelchair accessible
Sleep Inn & Suites Middletown - Goshen 
Middletown, NY
  • Up to 2500 guests
  • Select services
  • Indoor
  • Starts at $175

Dream better at The Sleep Inn & Suites hotel in Middletown, NY. We are near the Galleria at Crystal Run mall and are a simple stylish sanctuary that’s designed for a happy night’s rest. Our location off Interstate 84 makes it easy to enjoy hot air balloon rides, outdoor activities in the Poconos in Pennsylvania and attractions like: Hudson River, Holiday Mountain Ski Area and Monticello Raceway. You’ll find current, stylish design elements inspired by nature to refresh and relax around every corner at our affordable Middletown hotel. Our reasonable amenities simply complete your stay and include: Free breakfast ,Free WiFi, use of our indoor pool, fitness center, and business center. All of our guest rooms help you rest and unwind and include microwaves and refrigerators! Dream better at the Sleep Inn & Suites. Middletown hotels like ours are just as restful as home, but better–so that you leave with a smile on your face and a spring in your step.

Why you'll love this venue

  • Accommodates more than 200 guests
  • Wheelchair accessible
  • Dressing room available

Venue considerations

  • No in-house catering options
  • No built-in audiovisual options
  • Does not allow pets

Location flexible? Discover venues near Chester, NY

About wedding venues in Chester, NY

Why is New York the Perfect Wedding Destination?

New York gives you incredible variety for your special day, from Manhattan's iconic skyline to the charming countryside of Upstate. You can enjoy timeless elegance at The Plaza Hotel with its grand ballrooms overlooking Central Park, or take in breathtaking panoramic views of Manhattan at Tribeca Rooftop. Brooklyn offers photography-friendly industrial-chic spaces like The Foundry with its character-filled exposed brick and factory windows. Head Upstate and you'll find City Winery Hudson Valley where your celebration unfolds against the backdrop of a working vineyard with mountain views that change beautifully with each season. April sees the most wedding inquiries in New York, showing just how many couples are drawn to the region during spring's beautiful blooming season.

What's the Reality of Wedding Costs in New York?

Expect to pay more for your New York wedding than the national average of $6,500-$12,000 for venues alone. New York venues typically cost around $16,709 which makes up about 22% of your total wedding budget. Your overall costs will vary based on how many guests you're hosting:

Guest CountTotal Wedding Budget
50 guests (small wedding)$32,316
100 guests$54,844
150 guests$76,011
200 guests$94,911
250 guests$113,810
300 guests (large wedding)$132,709

Your other major expenses will include catering at $13,367 (18%), bar services running $10,694 (14%), florals at $8,177 (11%), planners costing $6,044 (8%), photography at $5,119 (7%), videography at $4,622 (6%), entertainment at $2,298 (3%), cake and desserts at $1,067 (1%), and hair and makeup averaging $550 (1%).

How Do NYC Wedding Venues Compare to Upstate Locations?

NYC venues offer you urban sophistication with distinctive skyline views. At Tribeca Rooftop + 360° you'll enjoy floor-to-ceiling windows showcasing Manhattan panoramas while The Plaza presents opulent ballrooms featuring chandeliers ornate molding and gold accents. The 620 Loft & Garden gives you a stunning rooftop terrace overlooking St. Patrick's Cathedral and Fifth Avenue.

Upstate venues surround you with natural beauty and historic architecture. City Winery Hudson Valley welcomes you to a renovated factory featuring vaulted ceilings stone walls and vineyard views. You can host up to 350 guests here and customize your outdoor ceremony areas to create exactly the atmosphere you're dreaming of.

Which New York Venues Offer Outstanding Culinary Experiences?

You can treat your guests to Two Michelin star cuisine at Manhatta perched 60 floors high in the Financial District where Executive Chef Justin Bogle creates memorable dishes like hamachi and black truffle dumplings. The River Cafe in Brooklyn serves Michelin-starred cuisine featuring Hudson Valley foie gras and Nantucket Bay scallops with Brooklyn Bridge views right outside your window. For a farm-to-table experience Blue Hill at Stone Barns in Westchester County offers cuisine sourced directly from their on-site farm with their HayLoft space accommodating anywhere from 40 to 260 guests.

Where Can You Find Accessible Wedding Venues in New York?

For couples prioritizing accessibility 620 Loft & Garden offers customizable settings that can work with various needs though you'll want to confirm specific features during your planning. Prospect Park Boathouse and Central Park Conservatory Garden provide accessible options with proper pathways for all your guests. Always ask about specific accommodations like wheelchair ramps elevators and accessible restrooms when you're researching potential venues to ensure everyone can fully participate in your celebration.

How Can Guests Participate Remotely at New York Weddings?

Historic Manhattan venues can make remote guests feel included by incorporating virtual tours during ceremony breaks while Midtown Loft & Terrace supports interactive platforms that go beyond simple passive streaming. You might consider venues in Chelsea or SoHo that can enhance those famous skyline views with live streaming that includes interactive elements like virtual photobooths live chats or virtual toasts. These features help create genuine engagement for participants joining your special day from afar.

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