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

The Jackson
Exterior

The Jackson

4.0 star property
10.0 out of 10, Exceptional, (188)
"Great people "
The price is AED 774
AED 852 total
includes taxes & fees
5 Jan - 6 January 2025
The Jackson
The Vesper
Room

The Vesper

3.0 star property
9.6 out of 10, Exceptional, (12)
"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 AED 488
AED 537 total
includes taxes & fees
6 Jan - 7 January 2025
The Vesper
Big Bears Lodge
Front of property

Big Bears Lodge

3.0 star property
8.8 out of 10, Excellent, (154)
"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 AED 612
AED 674 total
includes taxes & fees
5 Jan - 6 January 2025
Big Bears Lodge
The Inn at Manchester
Exterior

The Inn at Manchester

3.5 star property
10.0 out of 10, Exceptional, (223)
"Amazing friendly service. "
The price is AED 569
AED 626 total
includes taxes & fees
5 Jan - 6 January 2025
The Inn at Manchester
Stone Hearth Inn and Eatery
Front of property

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (75)
"Breakfast was great. The owner is super nice"
The price is AED 822
AED 896 total
includes taxes & fees
23 Dec - 24 Dec
Stone Hearth Inn and Eatery
Bromley View Inn
Restaurant

Bromley View Inn

3.5 star property
9.2 out of 10, Wonderful, (322)
"Very nice stay. Cozy and comfortable."
The price is AED 563
AED 620 total
includes taxes & fees
2 Jan - 3 January 2025
Bromley View 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 AED 921
AED 1,003 total
includes taxes & fees
8 Jan - 9 January 2025
Echo Lake Inn
Deerfield Valley Inn
Front of property

Deerfield Valley Inn

3.0 star property
9.8 out of 10, Exceptional, (37)
"no frills, but convenient, clean, attentive staff, "
The price is AED 537
AED 692 total
includes taxes & fees
23 Dec - 24 Dec
Deerfield Valley Inn
Colonel Williams Inn
Front of property

Colonel Williams Inn

3.0 star property
9.6 out of 10, Exceptional, (284)
"Great New England hospitality!....delicious breakfast and comfortable bedding. The location was great - between the small town of Wilmington, Mt. Snow and Brattleboro. Victoria and Brian could not have been more accommodating and friendly! Would definitely stay again when in the area. "
The price is AED 480
AED 523 total
includes taxes & fees
23 Dec - 24 Dec
Colonel Williams Inn
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
Harvest Barn Inn
Porch

Harvest Barn Inn

3.0 star property
9.8 out of 10, Exceptional, (197)
"No Complaints, Excellent breakfast "
The price is AED 693
AED 755 total
includes taxes & fees
3 Jan - 4 January 2025
Harvest Barn Inn
Stay At Jimmy's
Front of property

Stay At Jimmy's

3.0 star property
10.0 out of 10, Exceptional, (23)
"Our stay here was absolutely amazing! As soon as we walked in, we knew that we picked the right place. It was safe, clean and so close to downtown. John and Jimmy were the sweetest and made us feel right at home. We can’t recommend this place enough and will definitely be back!!"
The price is AED 915
AED 1,006 total
includes taxes & fees
2 Jan - 3 January 2025
Stay At Jimmy's
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 AED 716
AED 788 total
includes taxes & fees
23 Dec - 24 Dec
Deerhill Inn
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 AED 561
AED 609 total
includes taxes & fees
31 Dec - 1 January 2025
The Carriage Barn 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."
Blue Gentian Lodge at Magic Mountain
Inn on Putney Road
Exterior

Inn on Putney Road

4.0 star property
9.8 out of 10, Exceptional, (43)
"Great stop on our way out of N Vermont. Nice warm room on a cold night."
The price is AED 862
AED 948 total
includes taxes & fees
2 Jan - 3 January 2025
Inn on Putney Road
King & Queen Suite in Historic Inn Circa 1780
Room

King & Queen Suite in Historic Inn Circa 1780

9.6 out of 10, Exceptional, (14)
"This is a fine place to stay. Everything is thoughtfully provided to make guests comfortable. The bed was very high quality, too. There were snacks, breakfast options, and good coffee available in the morning. Nothing fancy, but very useful and much appreciated."
The price is AED 621
AED 963 total
includes taxes & fees
5 Jan - 6 January 2025
King & Queen Suite in Historic Inn Circa 1780
The Inn at Ormsby Hill
Terrace/patio

The Inn at Ormsby Hill

3.5 star property
9.8 out of 10, Exceptional, (115)
"Really liked the beautiful interior of the inn."
The price is AED 945
AED 1,039 total
includes taxes & fees
23 Dec - 24 Dec
The Inn at Ormsby Hill
Chesterfield Inn
Lobby

Chesterfield Inn

4.0 star property
9.0 out of 10, Wonderful, (101)
"Lots of things were lovely; fantastic room service food (unbelievably fresh and delicious, better than anywhere I’ve ever eaten in a hotel while traveling), beautiful serene natural setting, and wonderful design of the buildings plus COOKIES and tea in the afternoon. The service was also fantastic. The paint could use freshening and the bathroom grout needs redoing (or consider retiling). A piece of one window pane, a wood bit, fell off… so I stuck it back, obviously needs a proper repair. With...
The price is AED 1,129
AED 1,225 total
includes taxes & fees
7 Jan - 8 January 2025
Chesterfield Inn
Four Columns Inn
Garden

Four Columns Inn

3.0 star property
8.8 out of 10, Excellent, (3)
"Friendliest Staff Ever!"
Four Columns Inn
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

Long Trail House at Stratton Mountain Resort
Living room

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very Good, (72)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is AED 1,392
AED 1,731 total
includes taxes & fees
6 Jan - 7 January 2025
Long Trail House at Stratton Mountain Resort
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, (40)
"Like property— sad the lift that made it ski and in out was closed due weather conditions "
The price is AED 1,939
AED 2,618 total
includes taxes & fees
10 Jan - 11 January 2025
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Located in the Okemo Mt. Community, a mile to the base lodge

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

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 "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
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.