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Compare 47 B&B in Chester with updated reviews, rates, and availability.

Fireplace
The Jackson House Inn
4.0 star property
10.0 out of 10, Exceptional, (167)
"Fantastic homemade breakfast and cookies at night. The rooms were very clean and comfortable. The staff was fantastic! Will be staying again. Book directly and save money."
The price is $263
$289 total
includes taxes & fees
May 27 - May 28
The Jackson House Inn
Property grounds
The Inn at Manchester
3.5 star property
10.0 out of 10, Exceptional, (190)
"We had an excellent stay! Friendly and helpful check in, beautiful room, and delicious breakfasts. We also enjoyed some time in the bar room. If we are ever in the area again, we would definitely stay here again!"
The price is $155
$171 total
includes taxes & fees
May 19 - May 20
The Inn at Manchester
Front of property
Stay At Jimmy's
3.0 star property
10.0 out of 10, Exceptional, (1)
"Our short but sweet stay was great. Check in was smooth and the breakfast bundles were a nice touch. The rooms are newly designed and felt like such a getaway!"
The price is $199
$219 total
includes taxes & fees
May 19 - May 20
Stay At Jimmy's
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Seasonal outdoor pool
Golden Stage Inn B&B
3.5 star property
10.0 out of 10, Exceptional, (22)
"We chose this bed and breakfast based on others’ reviews- and you should, too! Our room was lovely and homey and had everything you’d want or need available. Mike and Julie are spectacularly thoughtful hosts. We felt welcomed, cared for, and a little bit spoiled :) during our three day stay. Will absolutely stay here again on our next visit to VT! "
Golden Stage Inn B&B
Exterior
Deerfield Valley Inn
3.0 star property
10.0 out of 10, Exceptional, (3)
"I had an absolutely wonderful stay at Dearfield Valley Inn in West Dover, VT. The charming ambiance, attentive staff, and cozy rooms made for a delightful experience. The inn's picturesque surroundings added to the overall charm, creating a perfect getaway. I highly recommend it for anyone seeking a peaceful and memorable stay in Vermont."
The price is $94
$124 total
includes taxes & fees
Jun 2 - Jun 3
Deerfield Valley Inn
Exterior
The Buckmaster Inn
3.0 star property
10.0 out of 10, Exceptional, (49)
"This Inn was built in 1801, so it’s a very old Inn. There are not enough superlatives. Fantastic. Awesome. Amazing. Going back definitely. All rooms are beautifully furnished with four-posters and very comfortable chairs. Place to be lived in. Immaculately clean. As soon as you walk in you want to stay forever. Warm. Delicious homemade breakfasts. Innkeeper Elizabeth is friendly and accommodating. We could have talked for hours. Still blissing out days later. "
The Buckmaster Inn
Front of property
The Woodstocker B&B
4.0 star property
10.0 out of 10, Exceptional, (50)
"This is a lovely and charming guest house / B&B, run by a very nice and friendly couple. During our stay they recommended a number of places to visit and were warm and welcoming every day. I would not hesitate to book with them again."
The Woodstocker B&B
Seasonal outdoor pool
The Brattleboro
3.0 star property
10.0 out of 10, Exceptional, (4)
"Peaceful, comfortable, great views. We were made welcome and had wonderful beverage and snack options and the Breakfast were Superior. We will definitely return. "
The Brattleboro
Exterior
Inn on Putney Road
4.0 star property
9.8 out of 10, Exceptional, (38)
"The Inn was so warm and comforting that it felt like home. It's beautifully decorated and you have access to the common areas where you can enjoy a game of pool, play piano, play a board game or find a nice book to read. The grounds are beautiful with flowers and plenty of seating. The owner Paul was very welcoming and included local snacks and sodas as well as waters in the room which I thought was a nice touch. The breakfast each morning was out of this world! Will definitely stay here again...
The price is $268
$295 total
includes taxes & fees
Jun 16 - Jun 17
Inn on Putney Road
Porch
Harvest Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (169)
"Excellent B&B! Very cozy and friendly, gourmet breakfasts. And the town is very cool and artsy, good coffee shops. "
The price is $155
$169 total
includes taxes & fees
May 17 - May 18
Harvest Barn Inn
Free daily continental breakfast
The Carriage Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (121)
"Joe went above and beyond for us. I recently had surgery and needed a chair to put in the shower (not the typical request) and he found me one within ten minutes of asking. He also had a lovely breakfast and was enjoy to talk to"
The price is $197
$214 total
includes taxes & fees
May 20 - May 21
The Carriage Barn Inn
Exterior
Deerhill Inn
3.5 star property
9.6 out of 10, Exceptional, (200)
"I would 100% stay here again! Incredibly caring, attentive, friendly hosts! We stayed in the Orchid room and it was beautiful. Whether it was remembering a small detail of one guest such as lactose intolerance or recommendations of things to do in town, the owners were always willing to help in any way they can. "
The price is $175
$193 total
includes taxes & fees
May 23 - May 24
Deerhill Inn
Front of property - evening/night
Woodbridge Inn
3.0 star property
9.6 out of 10, Exceptional, (57)
"Very nice experience. The people running the bed and breakfast were very nice "
Woodbridge Inn
Front of property
Colonel Williams Inn
3.0 star property
9.6 out of 10, Exceptional, (265)
"Beautiful Vermont Inn with exceptional breakfast: changes everyday - we had frittata, fresh fruit, steel cut oats fried with maple syrup and pecans and always muffins or other baked goods. Our hosts were friendly, accommodating and know the area well. We had room 3- spacious and comfortable. When it snows there is a 5 mile snowshoe,cross country trail on the property for guests only. We were there to attend a show at the Vermont Jazz Center in Brattleboro-about 20 min away. Also hiked...
The price is $134
$147 total
includes taxes & fees
May 19 - May 20
Colonel Williams Inn
Exterior detail
The One Cat B&B
2.5 star property
9.6 out of 10, Exceptional, (66)
"Wonderful selection of books, friendly hosts, happy colors."
The price is $187
$206 total
includes taxes & fees
May 29 - May 30
The One Cat B&B
View from property
The Inn at Ormsby Hill
3.5 star property
9.6 out of 10, Exceptional, (105)
"Great breakfast; grounds were beautiful; great innkeepers! Would recommend to others"
The price is $269
$296 total
includes taxes & fees
May 19 - May 20
The Inn at Ormsby Hill
Interior
King & Queen Suite in Historic Inn Circa 1780
9.6 out of 10, Exceptional, (13)
"SUCH a lovely, cozy stay in this beautiful VT town. Could not recommend more highly!"
The price is $119
$196 total
includes taxes & fees
May 18 - May 19
King & Queen Suite in Historic Inn Circa 1780
Lounge
Bromley View Inn
3.5 star property
9.2 out of 10, Wonderful, (311)
"Nice family oriented motel "
Bromley View Inn
Front of property
Stone Hearth Inn and Eatery
2.0 star property
9.0 out of 10, Wonderful, (48)
"Vicky and her family are wonderful hosts. We stayed on the last day of their season and received as welcoming a reception as you might expect at the height of the season. Stonehearth Inn is a labor of love and it shows. "
The price is $218
$238 total
includes taxes & fees
May 28 - May 29
Stone Hearth Inn and Eatery
Lobby
Chesterfield Inn
4.0 star property
9.0 out of 10, Wonderful, (100)
"A true find!"
The price is $301
$327 total
includes taxes & fees
May 19 - May 20
Chesterfield Inn
Don't see what you're looking for?
See all available properties in Chester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in Chester

Exterior
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (174)
"It was very clean and area is beautiful. The pictures did not show inside stairs and i just had back surgery. It was very difficult for me on stairs. I wish i knew that before booking.. Also the couch in living room was terrible to sit in. If they remodeled the upstairs, i would stay again. Thank you"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Exterior
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (177)
"We stayed the weekend for our 26th anniversary and had a wonderful time. Very private and everything was as described. The cottage is super charming! Will definitely be going back!"
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Fridge, microwave, oven, stovetop
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (30)
"My family really enjoyed this Lake House. The beautiful views of the lake were breathtaking. The house had everything we needed for preparing meals. The kitchen was functional and generally well equipped. The beds in the house were particularly comfortable. We enjoyed early morning coffee on the deck with perfect views of the lake. The location was great. Lots of wonderful hiking trials in close proximity. My only suggestion to the owners is to give the house a good deep cleaning. Nonetheless,...
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chester B&B information

Number of reviews
1,947
Accommodation
47 B&B
Lowest Price
$94
Highest Price
$301

Frequently asked questions

Searching for B&Bs in Chester?
If you’re looking for something a little different than your standard hotel experience, a bed and breakfast might be the perfect option for your vacation. When you want to explore some attractions in town, DaVallia Art & Accents and Bonnie’s Bundles Dolls are worth a stop.
Are you thinking about B&Bs over traditional hotel rooms?
With attentive service, opportunities to mingle with other guests, and hearty breakfasts, B&Bs provide a unique setting.
What are the top B&Bs in Chester?
Here are some B&Bs in the surrounding area: Stone Hearth Inn and Eatery: 8 rooms. 1.5 mi (2.3 km) from the heart of Chester. Enjoy the free buffet breakfast and unique décor. King & Queen Suite in Historic Inn Circa 1780: 0.3 mi (0.4 km) from the downtown core. Honeymoon Suite with Jacuzzi Tub in Historic Inn: Situated 0.3 mi (0.4 km) from the heart of Chester. Room in Historic Inn! 20 Minutes to Okemo!: 0.3 mi (0.4 km) from the heart of downtown.
How many Bed & Breakfasts should I expect to find in Chester?
Expedia has 7 B&Bs for your stay in Chester.
What's the best time of year to stay at a B&B in Chester?
When you’re dreaming of a escape to Chester, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.
What is there to do in Chester?
If you like to experience a new place through your taste buds, you’ll be sure to enjoy Chester for its coffeehouses and restaurants. If you’re looking to find something to do during your travels, you might consider checking out DaVallia Art & Accents and Bonnie’s Bundles Dolls. You might also consider a trip to sites like Vermont Country Store or Baltimore Covered Bridge if you have time to see more of the area.
How can I get to and around Chester?
You can map out your trip in and around Chester ahead of time with these transportation options. Fly into Springfield, VT (VSF-Hartness State), which is located 6.6 mi (10.7 km) away from the city center. Otherwise, look for flights into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 25.4 mi (40.8 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.

Recent reviews of Chester hotels
Expedia verified reviews