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Compare 48 B&B in Chester with updated reviews, rates, and availability.

Deerfield Valley Inn
Front of property
Deerfield Valley Inn
3.0 star property
9.8 out of 10, Exceptional, (33)
"The deer valley inn was a cozy small guesthouse . The staff were very kind and helpful. Highly recommend the place . The staff manager was originally from turkey. Really sorry I forgot the name at this moment but he was wonderful . "
The price is SAR 251
SAR 379 total
includes taxes & fees
24 Nov - 25 Nov
Deerfield Valley Inn
The Jackson House Inn
Exterior
The Jackson House Inn
4.0 star property
10.0 out of 10, Exceptional, (180)
"Such a beautiful inn! Breakfast was amazing. "
The price is SAR 745
SAR 819 total
includes taxes & fees
24 Nov - 25 Nov
The Jackson House Inn
Colonel Williams Inn
Front of property
Colonel Williams Inn
3.0 star property
9.6 out of 10, Exceptional, (283)
"My boyfriend and I had a fabulous stay here this past weekend! Stayed here for the night so we could try a restaurant in Brattleboro and it was the perfect 15 min drive. The room was very clean and had a beautiful view of the pond. The staff was incredibly friendly and ready upon our arrival. The lounge/ living room was cozy for watching a movie at night and the breakfast was absolutely to die for! "
The price is SAR 520
SAR 567 total
includes taxes & fees
10 Dec - 11 Dec
Colonel Williams Inn
The Vesper
Room
The Vesper
3.0 star property
9.6 out of 10, Exceptional, (11)
"Dana and her staff were so welcoming and our experience was nothing less than perfect. My husband and I travel for a living and I feel like The Vesper is a little hidden gem that we have discovered and we look forward to staying there again. Stephanie Louris Ps.. Breakfast was so delicious!!"
The price is SAR 577
SAR 635 total
includes taxes & fees
25 Nov - 26 Nov
The Vesper
Stay At Jimmy's
Front of property
Stay At Jimmy's
3.0 star property
10.0 out of 10, Exceptional, (21)
"Wow! Loved our visit at Stay at Jimmy's. Room was beautifully decorated and supplied with everything we needed. Location was perfect for exploring Woodstock. We had excellent communication from John and Jimmy. A bonus for us was the EV charging station across the street. "
The price is SAR 935
SAR 1,028 total
includes taxes & fees
24 Nov - 25 Nov
Stay At Jimmy's
Stone Hearth Inn and Eatery
Front of property
Stone Hearth Inn and Eatery
3.0 star property
9.2 out of 10, Wonderful, (73)
"If you’re looking for an authentic experience in a 200 year old home - with tons of wonderful history and true early American character - you’ll love this stay! This is NOT a shiny new hotel, with all the conveniences. You can forget your free “make-your-own hot breakfast” deal. This chef-curated breakfast was fresh, carefully crafted, and delicious! The eggs were light, fluffy and flavorful. The bacon was thick and cooked perfectly. And OMG, the homemade Belgian waffles were literally covered...
The price is SAR 672
SAR 733 total
includes taxes & fees
27 Nov - 28 Nov
Stone Hearth Inn and Eatery
The Inn at Manchester
Exterior
The Inn at Manchester
3.5 star property
10.0 out of 10, Exceptional, (218)
"Great stay to end out our Vermont honeymoon."
The price is SAR 582
SAR 640 total
includes taxes & fees
24 Nov - 25 Nov
The Inn at Manchester
The Carriage Barn Inn
Exterior
The Carriage Barn Inn
3.0 star property
9.6 out of 10, Exceptional, (142)
"Lovely old BnB, easy to find, very convenient Very clean room Great continental breakfast Loved ease of walking to downtown, many stores and restaurants Informative and very friendly and helpful owner"
The price is SAR 679
SAR 737 total
includes taxes & fees
24 Nov - 25 Nov
The Carriage Barn Inn
Bromley View Inn
Restaurant
Bromley View Inn
3.5 star property
9.2 out of 10, Wonderful, (322)
"Very nice stay. Cozy and comfortable."
Bromley View Inn
Deerhill Inn
Exterior
Deerhill Inn
3.5 star property
9.6 out of 10, Exceptional, (211)
"The innkeepers were such nice, friendly, helpful people, going out of their way to see that we had a delicious breakfast before our early departure. We loved everything about this inn! "
The price is SAR 732
SAR 805 total
includes taxes & fees
27 Nov - 28 Nov
Deerhill Inn
Harvest Barn Inn
Porch
Harvest Barn Inn
3.0 star property
9.8 out of 10, Exceptional, (194)
"Such an excellent stay. Beautiful view, felt safe and quiet. Blessing was kind enough to make us breakfast in the morning, highly recommended "
The price is SAR 591
SAR 645 total
includes taxes & fees
3 Dec - 4 Dec
Harvest Barn Inn
Big Bears Lodge
Front of property
Big Bears Lodge
3.0 star property
8.8 out of 10, Excellent, (153)
"Very quaint place to stay; the owners are sweet and considerate! They make the place feel like a safe get-away to somewhere nostalgic. I will definitely be booking a stay here again! "
The price is SAR 604
SAR 665 total
includes taxes & fees
23 Nov - 24 Nov
Big Bears Lodge
The Buckmaster Inn
Property entrance
The Buckmaster Inn
3.0 star property
10.0 out of 10, Exceptional, (56)
"Elizabeth and Richard were absolutely wonderful hosts! I enjoyed every second of staying at this property. They went out of their way to be hospitable and to make all guests comfortable. The breakfast was fantastic each day and they had wonderful suggestions for the local area. I was already planning a trip back before I had even checked out. Highly recommend!!"
The Buckmaster Inn
Echo Lake Inn
Front of property
Echo Lake Inn
2.5 star property
8.6 out of 10, Excellent, (94)
"Old fashioned inn with wonderful hosts."
The price is SAR 930
SAR 1,014 total
includes taxes & fees
11 Dec - 12 Dec
Echo Lake Inn
Windham Hill Inn
Exterior
Windham Hill Inn
3.0 star property
8.2 out of 10, Very Good, (32)
"The rustic charm of a beautifully renovated New England barn, with spacious rooms that provide quiet solitude and comfortable furnishings, wall to wall! The king size bed, the oversized bathroom with a giant jetted tub beneath a skylight…SO INCREDIBLY PEACEFUL!! And outdoors there are numerous trails and Adirondack chairs placed at scenic spots to take in the beauty of the land in front of you and to enjoy the star filled wide-open sky above at night, which we did and thoroughly enjoyed! We...
The price is SAR 777
SAR 847 total
includes taxes & fees
5 Dec - 6 Dec
Windham Hill Inn
Blue Gentian Lodge at Magic Mountain
Property entrance
Blue Gentian Lodge at Magic Mountain
2.5 star property
9.0 out of 10, Wonderful, (92)
"Very welcoming host."
The price is SAR 672
SAR 739 total
includes taxes & fees
24 Nov - 25 Nov
Blue Gentian Lodge at Magic Mountain
The One Cat B&B
Property entrance
The One Cat B&B
2.5 star property
9.6 out of 10, Exceptional, (74)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
The One Cat B&B
The Inn at Ormsby Hill
Terrace/patio
The Inn at Ormsby Hill
3.5 star property
9.8 out of 10, Exceptional, (113)
"What a beautiful B&B! The staff was super kind and friendly. Loved my room and how it was so nicely decorated. Cozy and comfortable. Breakfast was great and town was just a 5 minute drive away. So glad my last minute decision to visit Vermont turned out so perfect. ❤️"
The price is SAR 1,085
SAR 1,193 total
includes taxes & fees
24 Nov - 25 Nov
The Inn at Ormsby Hill
Golden Stage Inn B&B
Front of property
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
Inn on Putney Road
Exterior
Inn on Putney Road
4.0 star property
9.8 out of 10, Exceptional, (42)
"A lovely four day stay in Vermont. Inn was perfect, with gardens to enjoy and lots of lounges and nooks to spend time and read. We had a suite with a separate sitting room, which allowed us to have our daughter accompany us on a last minute visit. Paul and his staff are super accommodating and are genuinely friendly hosts. Paul also cooks all the breakfasts which are superb! Different breakfasts each day, beautifully presented and absolutely delicious!"
The price is SAR 1,002
SAR 1,102 total
includes taxes & fees
26 Nov - 27 Nov
Inn on Putney Road
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.
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Other property types in Chester

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (39)
"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Outdoor spa tub
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
9.8 out of 10, Exceptional, (196)
"A few weeks ago my partner and I stayed at the Hideway Cabin for the fifth year in a row. We made this a yearly tradition of ours. I cannot say enough about the place! The cabin very clean and cozy. The kitchen and bedrooms are stocked with all the necessities. It is located only a few, short minutes from Ludlow's center of town. The hot tub is amazing. I love seeing the stars shining bright at night. Highly recommend!"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off!
Located in the Okemo Mt. Community, a mile to the base lodge
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off!
9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off!
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.

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?
This is a B&B that Expedia travelers like in Chester: Stone Hearth Inn and Eatery: 8 rooms. Enjoy the free buffet breakfast and unique décor.
How many Bed & Breakfasts should I expect to find in Chester?
Expedia has 6 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 Okemo Mountain Resort or Stratton Mountain Resort 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.