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Check prices for these dates

Next weekend
Apr 17 - Apr 19
In two weeks
Apr 24 - Apr 26
In one month
May 8 - May 10
In two months
Jun 5 - Jun 7

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, (118 reviews)
"Great stay! Very cozy and homey. Very yummy breakfast! "
United States
Olena
The price is ￥29,477
￥32,130 total
includes taxes & fees
Apr 15 - Apr 16
Stone Hearth Inn and Eatery
Lounge

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (438 reviews)
"We had an enjoyable stay and would stay again. "
United States
Donna
The price is ￥12,658
￥13,925 total
includes taxes & fees
Apr 13 - Apr 14
Bromley View Inn
Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (257 reviews)
"Staff were wonderful, food was excellent, environment was peaceful, everything was clean and in decent condition."
United States
Charles
The price is ￥19,729
￥21,505 total
includes taxes & fees
Apr 12 - Apr 13
Harvest Barn Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful location and nice staff."
United States
Cynthia
The price is ￥20,278
￥22,103 total
includes taxes & fees
Apr 12 - Apr 13
Four Columns Inn
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (171 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is ￥20,679
￥22,437 total
includes taxes & fees
Apr 20 - Apr 21
The Carriage Barn Inn
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (350 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is ￥23,225
￥25,547 total
includes taxes & fees
Apr 26 - Apr 27
Colonel Williams Inn
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (115 reviews)
"Great location Host Oz cooked up a great breakfast Room was fine for one person "
United States
michael
The price is ￥11,177
￥16,656 total
includes taxes & fees
Apr 13 - Apr 14
Deerfield Valley Inn
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (57 reviews)
"Uniqueness of rooms, breakfast options and walking distance to so many great spots!"
United States
Emily
The price is ￥20,067
￥22,075 total
includes taxes & fees
Apr 20 - Apr 21
The Vesper
Front of property

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (79 reviews)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is ￥39,244
￥43,167 total
includes taxes & fees
Apr 12 - Apr 13
The One Cat B&B
Property grounds

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (305 reviews)
"Staff was exceptionally friendly…lovely Inn! Beautiful views "
United States
Michael
The price is ￥26,162
￥28,778 total
includes taxes & fees
May 10 - May 11
The Inn at Manchester
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, (40 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 ￥26,971
￥29,399 total
includes taxes & fees
Apr 20 - Apr 21
Windham Hill Inn
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (57 reviews)
"Room was super clean and the hosts are excellent. "
United States
Joe
The price is ￥39,569
￥43,527 total
includes taxes & fees
Apr 12 - Apr 13
Inn on Putney Road
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (277 reviews)
"Easy Check-In; Lovely Room; Great Location & Atmosphere. The staff was very friendly,"
United States
Michael
The price is ￥30,317
￥33,349 total
includes taxes & fees
May 5 - May 6
The Jackson
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (1 review)
"The property manager greeted us when we walked in and she was extremely friendly and kind. The inn was charming and had a homey feel, and the rooms were very clean and well maintained with awesome amenities."
United States
Sara
The price is ￥39,348
￥43,282 total
includes taxes & fees
Apr 13 - Apr 14
Deer Brook Inn
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 ￥11,654
￥20,765 total
includes taxes & fees
Apr 19 - Apr 20
Room 7 - family room sleeps 4
Garden

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (210 reviews)
"Great mom and pop motel minutes from Mount Snow"
United States
Richard
The price is ￥27,352
￥30,089 total
includes taxes & fees
Apr 10 - Apr 11
Big Bears Lodge
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, (160 reviews)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
The price is ￥36,960
￥40,657 total
includes taxes & fees
Apr 13 - Apr 14
The Inn at Ormsby Hill
Exterior detail

Sleep Woodstock Mobility Impaired Accessible Suite

Sleep Woodstock Mobility Impaired Accessible Suite
Woodstock
The price is ￥11,654
￥20,608 total
includes taxes & fees
Apr 13 - Apr 14
Sleep Woodstock Mobility Impaired Accessible Suite
Exterior

The Woodstocker B&B

The Woodstocker B&B
4.0 star property
Woodstock
10.0 out of 10, Exceptional, (51 reviews)
"This food at this property is amazing!! I would come back any day, the bread and entire menu is incredible. The zagat should try their breakfast! "
United States
Kavina
The price is ￥43,796
￥48,175 total
includes taxes & fees
Apr 10 - Apr 11
The Woodstocker B&B
Front of property - evening/night

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (105 reviews)
"Great stay"
United States
Wayne
The price is ￥47,749
￥51,808 total
includes taxes & fees
Apr 19 - Apr 20
Chesterfield 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

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

10/10 Excellent
"Was perfect for ski weekend. Will come back for sure!"
Brett 2-night trip
Posted 1 day ago
Hideaway Inn Mt. Snow

Find out more about Chester

Chester B&B information

Number of reviews
2,204
Accommodation
62 B&B
Lowest Price
￥13,925
Highest Price
￥51,808

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 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. Situated 17.8 mi (28.6 km) from the heart of Chester. 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 Vermont Country Store or Lowell Lake State Park 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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