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Check prices for these dates

Next weekend
Mar 13 - Mar 15
In two weeks
Mar 20 - Mar 22
In one month
Apr 3 - Apr 5
In two months
May 1 - May 3

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, (115 reviews)
"So great all around!"
United States
Janet
The price is ￥30,224
￥32,944 total
includes taxes & fees
Mar 9 - Mar 10
Stone Hearth Inn and Eatery
Lounge

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (426 reviews)
"Clean room/ great breakfast"
United States
Ryan
Bromley View Inn
Room 4 | Hypo-allergenic bedding, free WiFi, bed sheets

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (349 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is ￥23,104
￥25,414 total
includes taxes & fees
Mar 31 - Apr 1
Colonel Williams Inn
Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (253 reviews)
"Everything was great. Awesome hosts, room, common areas and a fabulous breakfast. Can’t recommend too highly."
United States
Mark
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, (169 reviews)
"Very helpful and welcoming host. "
United States
Bruce
The price is ￥21,677
￥23,519 total
includes taxes & fees
Apr 2 - Apr 3
The Carriage Barn Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (23 reviews)
"Everything was great 👍 I will stay there again and highly recommend to others "
United States
Linda
Four Columns Inn
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 ￥38,234
￥42,057 total
includes taxes & fees
Mar 12 - Mar 13
The One Cat B&B
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (272 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
Exterior

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (290 reviews)
"super cute and clean, felt like home after not living there for 4 years!"
United States
MacLean
The price is ￥25,950
￥28,545 total
includes taxes & fees
Mar 4 - Mar 5
The Inn at Manchester
Property grounds

Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (115 reviews)
"Host was wonderful. "
United States
Robert
The price is ￥26,817
￥29,498 total
includes taxes & fees
Mar 12 - Mar 13
Blue Gentian Lodge at Magic Mountain
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (57 reviews)
"Charming bed and breakfast"
United States
Nicholas
The price is ￥24,577
￥27,035 total
includes taxes & fees
Mar 12 - Mar 13
The Vesper
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 ￥27,346
￥29,808 total
includes taxes & fees
Mar 16 - Mar 17
Windham Hill Inn
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
The price is ￥35,756
￥39,332 total
includes taxes & fees
Mar 15 - Mar 16
Deer Brook 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 ￥36,609
￥40,270 total
includes taxes & fees
Mar 12 - Mar 13
Inn on Putney Road
Dining

Alpine 5, cozy Vermont retreat

Alpine 5, cozy Vermont retreat
Manchester
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay! The room was very clean and spacious, which made it extremely comfortable and relaxing. Everything was well maintained and exactly as described. The space felt fresh, organized, and welcoming from the moment we arrived.Overall, a great experience, and we would definitely stay here again. Highly recommend!"
United States
Shuo P.
The price is ￥11,559
￥20,596 total
includes taxes & fees
Mar 5 - Mar 6
Alpine 5, cozy Vermont retreat
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
3.0 star property
West Dover
9.4 out of 10, Exceptional, (112 reviews)
"Great location Host Oz cooked up a great breakfast Room was fine for one person "
United States
michael
Deerfield Valley Inn
Garden

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (203 reviews)
"Great mom and pop motel minutes from Mount Snow"
United States
Richard
The price is ￥26,919
￥29,612 total
includes taxes & fees
Mar 31 - Apr 1
Big Bears Lodge
Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (48 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is ￥46,659
￥51,325 total
includes taxes & fees
Mar 5 - Mar 6
Stay At Jimmy's
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, (156 reviews)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
The price is ￥38,289
￥42,118 total
includes taxes & fees
Mar 8 - Mar 9
The Inn at Ormsby Hill
Exterior

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (100 reviews)
"Food was excellent. Room was clean and cozy. Staff were all incredibly welcoming and friendly. Perfect location. Would highly recommend. "
United States
Danielle
The price is ￥35,608
￥38,812 total
includes taxes & fees
Apr 1 - Apr 2
Echo Lake 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 Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"Shuttle if very efficient and the wait is never long to get to the slopes and village area. Great area for walks and/or with dogs. Although I was hoping for pancakes or waffles with the continental breakfast but was great nonetheless. Had dinner reservations in the village and the shuttle was the way to go on a super cold night. It’s just what you need to be comfortable. Hot tub and sauna was refreshing. I’d would deff recommend staying there again. "
Cherish Kae 1-night trip
Posted 18 hours ago
The Black Bear Lodge at Stratton Mountain Resort

Find out more about Chester

Chester B&B information

Number of reviews
2,764
Accommodation
62 B&B
Lowest Price
￥23,519
Highest Price
￥51,325

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 Stratton Mountain Resort or Vermont Country Store 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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