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Check prices for these dates

Next weekend
30 Jan - 1 Feb
In two weeks
6 Feb - 8 Feb
In one month
20 Feb - 22 Feb
In two months
20 Mar - 22 Mar

Our top choices for Chester bed & breakfast

Front of property

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (109 reviews)
"So great all around!"
United States
Janet
The price is SAR 1,093
SAR 1,191 total
includes taxes & fees
2 Feb - 3 Feb
Stone Hearth Inn and Eatery
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.6 out of 10, Exceptional, (19 reviews)
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
Four Columns Inn
Lounge

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (416 reviews)
"Gem of an older ski bed n breakfast "
United States
Martin
Bromley View Inn
Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (246 reviews)
"Gourmet breakfast, quiet and beautiful scenery. Loved it!!!!!"
United States
RICHARD
Harvest Barn Inn
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (167 reviews)
"Very helpful and welcoming host. "
United States
Bruce
The price is SAR 504
SAR 547 total
includes taxes & fees
29 Jan - 30 Jan
The Carriage Barn Inn
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (343 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is SAR 549
SAR 604 total
includes taxes & fees
1 Feb - 2 Feb
Colonel Williams Inn
Property grounds

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (285 reviews)
"super cute and clean, felt like home after not living there for 4 years!"
United States
MacLean
The price is SAR 619
SAR 681 total
includes taxes & fees
25 Jan - 26 Jan
The Inn at Manchester
Front of property

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78 reviews)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is SAR 557
SAR 613 total
includes taxes & fees
26 Jan - 27 Jan
The One Cat B&B
Property grounds

Room 7 - family room sleeps 4

Room 7 - family room sleeps 4
Manchester
10.0 out of 10, Exceptional, (1 review)
"Nice spot, good location. Towels could be better, but overall a great spot. "
United States
Kuan-Chung
The price is SAR 791
SAR 1,092 total
includes taxes & fees
6 Feb - 7 Feb
Room 7 - family room sleeps 4
Kayaking

Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (113 reviews)
"Lovely pleasant stay. "
United States
Heather
The price is SAR 644
SAR 709 total
includes taxes & fees
1 Feb - 2 Feb
Blue Gentian Lodge at Magic Mountain
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
3.0 star property
West Dover
9.6 out of 10, Exceptional, (98 reviews)
"Staff was great and the location is very close to the ski area. Cozy atmosphere at hotel."
Canada
Shane
Deerfield Valley Inn
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (262 reviews)
"The Jackson Inn is incredibly charming and in a picturesque area. The room was very comfortable and the restaurant and staff was amazing."
United States
Abby
The price is SAR 672
SAR 739 total
includes taxes & fees
25 Jan - 26 Jan
The Jackson
Garden

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (189 reviews)
"Hot tub was nice and hot, fits 6 people so could get a little crowded if they are booked up. the property is dated but kept up very well. Breakfast was perfect and made to order. Eggs with bacon or sausage, french toast. Simple but all you need before going out to ski in the morning. "
United States
agata
The price is SAR 668
SAR 735 total
includes taxes & fees
26 Jan - 27 Jan
Big Bears Lodge
Room, 1 Queen Bed, Garden View | Mountain view

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.4 out of 10, Very Good, (38 reviews)
"This place was amazing, beautiful and the staff was great. We will be coming back here again. Visit the waterfalls in the area, beautiful. Great romantic getaway. "
United States
Brandon
The price is SAR 659
SAR 718 total
includes taxes & fees
29 Jan - 30 Jan
Windham Hill Inn
Front of property - evening/night

The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (152 reviews)
"Love this place! Have stayed here twice now and will again. Great location, beautiful rooms, delicious breakfast and very friendly owners. A+"
United States
cynthia
The price is SAR 859
SAR 945 total
includes taxes & fees
25 Jan - 26 Jan
The Inn at Ormsby Hill
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (56 reviews)
"wonderful atmosphere, great breakfast, friedly staff, great location"
United States
Kurt
The price is SAR 880
SAR 968 total
includes taxes & fees
25 Jan - 26 Jan
Inn on Putney Road
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (53 reviews)
"Charming bed and breakfast"
United States
Nicholas
The price is SAR 657
SAR 723 total
includes taxes & fees
25 Jan - 26 Jan
The Vesper
Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (47 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is SAR 934
SAR 1,027 total
includes taxes & fees
25 Jan - 26 Jan
Stay At Jimmy's
Front of property - evening/night

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104 reviews)
"Great stay"
United States
Wayne
The price is SAR 1,153
SAR 1,251 total
includes taxes & fees
1 Feb - 2 Feb
Chesterfield Inn
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
The price is SAR 1,042
SAR 1,146 total
includes taxes & fees
11 Feb - 12 Feb
Deer Brook 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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Top Chester Hotel Reviews

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

10/10 Excellent
"We have been staying at the Equinox for over 35 yrs. Love the whole scene and vibe. Love the pool and hot tub. Love the big real wood fireplace. "
Patricia 4-night trip
Posted 3 hours ago
The Equinox Golf Resort & Spa

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. Bromley View Inn: 16 rooms. 17.8 mi (28.6 km) from the downtown core. Enjoy the unique décor and fireplace in the lobby.
How many Bed & Breakfasts should I expect to find in Chester?
Expedia has 5 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.