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Check prices for these dates

Next weekend
5 Jun - 7 Jun
In two weeks
12 Jun - 14 Jun
In one month
26 Jun - 28 Jun
In two months
24 Jul - 26 Jul

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 €195
includes taxes & fees
15 Jun - 16 Jun
Stone Hearth Inn and Eatery
Lounge

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (442 reviews)
"We had an enjoyable stay and would stay again. "
United States
Donna
The price is €80
includes taxes & fees
3 Jun - 4 Jun
Bromley View Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (39 reviews)
"The hot tub was so amazing"
United States
Mark
The price is €122
includes taxes & fees
1 Jun - 2 Jun
Four Columns Inn
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (354 reviews)
"Great breakfast!"
United States
Billie
The price is €149
includes taxes & fees
1 Jun - 2 Jun
Colonel Williams Inn
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (281 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
The price is €149
includes taxes & fees
4 Jun - 5 Jun
The Jackson
Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (266 reviews)
"Excellent hosts provided a terrific stay!"
United States
Mark
The price is €163
includes taxes & fees
1 Jun - 2 Jun
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, (172 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is €165
includes taxes & fees
1 Jun - 2 Jun
The Carriage Barn Inn
Kayaking

Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (118 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
Blue Gentian Lodge at Magic Mountain
Property grounds

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (319 reviews)
"Had a wonderful stay. Staff very pleasant."
United States
Ellen
The price is €149
includes taxes & fees
14 Jun - 15 Jun
The Inn at Manchester
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (120 reviews)
"Great location Host Oz cooked up a great breakfast Room was fine for one person "
United States
michael
The price is €99
includes taxes & fees
2 Jun - 3 Jun
Deerfield Valley Inn
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (62 reviews)
"This was the cutest little bed and breakfast. The staff was lovely, the check-in was easy, and we had a great time in Woodstock! "
United States
Melissa
The price is €165
includes taxes & fees
8 Jun - 9 Jun
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, (80 reviews)
"Breakfast was fantastic Did not need any shops Hosts were super friendly We enjoyed our short stay"
United States
marjie
The price is €236
includes taxes & fees
3 Jun - 4 Jun
The One Cat B&B
Room, 1 Queen Bed, Garden View | Mountain view

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (41 reviews)
"The room was wonderful. SO spacious and well-appointed, extremely clean. Loved the excellent bedding, the soaking tub, the perfect water pressure in the shower. We did not expect the flat-screen TV, so it was a treat to have. Don't let the lack of restaurant bother you: There are plenty of great choices around, though you have a bit of a drive. For a leisurely romantic weekend, I can't think of a better place. "
United States
Debbie
The price is €174
includes taxes & fees
11 Jun - 12 Jun
Windham Hill Inn
Exterior

Room 1, peaceful retreat in Manchester - King bed

Room 1, peaceful retreat in Manchester - King bed
Manchester
10.0 out of 10, Exceptional, (1 review)
"The room was spotless. The communal guest kitchen is an awesome feature. "
United States
Jacob
The price is €112
includes taxes & fees
2 Jun - 3 Jun
Room 1, peaceful retreat in Manchester - King bed
Exterior

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (58 reviews)
"Fabulous home, breakfast, staff, and location. Excellent value! Will definitely be back!"
United States
Mary
The price is €268
includes taxes & fees
1 Jun - 2 Jun
Inn on Putney Road
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (2 reviews)
"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 €220
includes taxes & fees
2 Jun - 3 Jun
Deer Brook Inn
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 €215
includes taxes & fees
1 Jun - 2 Jun
Echo Lake Inn
Exterior

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
Sleep Woodstock - 2 Double Beds - Dog Friendly
Garden

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (214 reviews)
"Place is great and location as well, 5 minutes from Mount Snow."
United States
Matheus
The price is €163
includes taxes & fees
2 Jun - 3 Jun
Big Bears Lodge
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 €280
includes taxes & fees
1 Jun - 2 Jun
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

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent
"The reception area looked inviting. The staff were friendly. The unit we stayed in was good and clean with enough sleeping areas for our family (2 bedrooms plus a sofa bed) and 2 bathrooms. We were not able to use the other amenities so I can’t say if they are good or not."
Leoda 1-night trip
Posted 2 hours ago
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Find out more about Chester

Chester B&B information

Number of reviews
2,204
Accommodation
77 B&B
Lowest Price
€80
Highest Price
€280

Frequently asked questions

Searching for B&Bs in Chester?
If you're hoping for something a little different than your standard hotel experience, a bed and breakfast might be the perfect option for your trip. When you want to explore some attractions in town, DaVallia Art & Accents and Bonnie's Bundles Dolls are worth a stop.
Are you considering an apartment for your stay?
With attentive service, opportunities to meet guests from other places and delectable breakfasts, B&Bs all have a unique setting.
What are the top B&Bs in Chester?
This is a B&B that Expedia travellers like in Chester: Stone Hearth Inn and Eatery: 8 rooms. Enjoy the free buffet breakfast and unique decor.
How many bed & breakfasts should I expect to find in Chester?
Expedia has 5 B&Bs for your getaway in Chester.
What's the best time of year to stay at a B&B in Chester?
When you're dreaming of a getaway to Chester, make sure that you take the year-round temperatures into account. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.
What is there to do in Chester?
If you like to experience a new place through your taste buds, you'll definitely enjoy Chester for its coffee shops and restaurants. If you're looking to find something to do during your travels, you might consider visiting DaVallia Art & Accents and Bonnie's Bundles Dolls. You might also consider a trip to sites such as 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 centre. You can also search 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, consider renting a car to explore more sights.