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Check prices for these dates

Next weekend
Feb 13 - Feb 15
In two weeks
Feb 20 - Feb 22
In one month
Mar 6 - Mar 8
In two months
Apr 3 - Apr 5

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, (111 reviews)
"So great all around!"
United States
Janet
The price is ₩407,400
₩444,066 total
includes taxes & fees
Feb 4 - Feb 5
Stone Hearth Inn and Eatery
Lounge

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (419 reviews)
"Clean room/ great breakfast"
United States
Ryan
Bromley View Inn
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
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
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (344 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is ₩228,704
₩251,574 total
includes taxes & fees
Feb 11 - Feb 12
Colonel Williams 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 ₩201,704
₩218,849 total
includes taxes & fees
Feb 4 - Feb 5
The Carriage Barn 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, (287 reviews)
"super cute and clean, felt like home after not living there for 4 years!"
United States
MacLean
The price is ₩238,352
₩262,187 total
includes taxes & fees
Feb 8 - Feb 9
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 ₩216,684
₩238,352 total
includes taxes & fees
Feb 5 - Feb 6
The One Cat B&B
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 ₩258,576
₩284,433 total
includes taxes & fees
Feb 4 - Feb 5
Blue Gentian Lodge at Magic Mountain
Garden

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (194 reviews)
"Great mom and pop motel minutes from Mount Snow"
United States
Richard
The price is ₩257,493
₩283,235 total
includes taxes & fees
Feb 10 - Feb 11
Big Bears Lodge
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (264 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 Jackson
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, (154 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 ₩332,529
₩365,783 total
includes taxes & fees
Feb 4 - Feb 5
The Inn at Ormsby Hill
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)
"We had a fantastic room! Staff was very friendly and accommodating. Though we visited during peak foliage season, we’ll be trying to book again in the near future to try out the pool."
United States
J
The price is ₩273,022
₩297,594 total
includes taxes & fees
Feb 9 - Feb 10
Windham Hill Inn
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 ₩338,894
₩372,783 total
includes taxes & fees
Feb 5 - Feb 6
Inn on Putney Road
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
The price is ₩341,241
₩375,365 total
includes taxes & fees
Mar 3 - Mar 4
Deer Brook Inn
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (55 reviews)
"Charming bed and breakfast"
United States
Nicholas
The price is ₩268,139
₩294,964 total
includes taxes & fees
Feb 11 - Feb 12
The Vesper
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
3.0 star property
West Dover
9.6 out of 10, Exceptional, (102 reviews)
"Staff was great and the location is very close to the ski area. Cozy atmosphere at hotel."
Canada
Shane
Deerfield Valley Inn
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 ₩444,116
₩481,862 total
includes taxes & fees
Feb 12 - Feb 13
Chesterfield Inn
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 ₩431,923
₩475,115 total
includes taxes & fees
Feb 10 - Feb 11
Stay At Jimmy's
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 Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Woodstock is a magical place! We love staying at the Shire! They really make it feel like home! So cozy! The staff is very friendly and accommodating! We will always stay at the Shire!"
Stephanie 3-night trip
Posted 4 days ago
The Shire Woodstock

Find out more about Chester

Chester B&B information

Number of reviews
2,682
Accommodation
29 B&B
Lowest Price
₩218,849
Highest Price
₩481,862

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, Bonnie's Bundles Dolls and DaVallia Art & Accents 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 Bonnie's Bundles Dolls and DaVallia Art & Accents. 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.

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