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Check prices for these dates

Next weekend
9 Jan - 11 Jan
In two weeks
16 Jan - 18 Jan
In one month
30 Jan - 1 Feb
In two months
27 Feb - 1 Mar

Our top choices for Chester bed & breakfast

Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (107)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is AED 767
AED 836 total
includes taxes & fees
5 Jan - 6 Jan
Stone Hearth Inn and Eatery
Garden
Four Columns Inn

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (16)
"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

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (406)
"Clean and great location with fun lounge area."
United States
Marshall
Bromley View Inn
Porch
Harvest Barn Inn

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (244)
"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

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (165)
"Excellent place!!!! Lovely room that had all I needed!!! The bed was comfortable and the stay was wonderful!!!!!!"
United States
natalia
The price is AED 459
AED 498 total
includes taxes & fees
4 Jan - 5 Jan
The Carriage Barn Inn
Exterior
The One Cat B&B

The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.6 out of 10, Exceptional, (78)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is AED 481
AED 529 total
includes taxes & fees
4 Jan - 5 Jan
The One Cat B&B
Front of property
Colonel Williams Inn

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (340)
"Very nice historic inn. We enjoyed our stay. Breakfast was exceptional."
United States
scott
The price is AED 550
AED 605 total
includes taxes & fees
6 Jan - 7 Jan
Colonel Williams Inn
Property grounds
The Inn at Manchester

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (282)
"Charming bed and breakfast found on a whim. Captures New England charm and the owners are so nice and hospitable. Really liked the bar as well to mingle with locals. Will definitely be returning again!"
United States
Amy
The price is AED 606
AED 667 total
includes taxes & fees
4 Jan - 5 Jan
The Inn at Manchester
Kayaking
Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (113)
"Lovely pleasant stay. "
United States
Heather
The price is AED 644
AED 709 total
includes taxes & fees
4 Jan - 5 Jan
Blue Gentian Lodge at Magic Mountain
Mountain view
Windham Hill Inn

Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.4 out of 10, Very Good, (38)
"Did not use"
United States
Douglas
The price is AED 694
AED 757 total
includes taxes & fees
5 Jan - 6 Jan
Windham Hill Inn
Front of property
The Jackson

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (259)
"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
Garden
Big Bears Lodge

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (185)
"The owners were wonderful: kind, interesting to talk to, and very hospitable."
United States
Margaret
The price is AED 655
AED 720 total
includes taxes & fees
4 Jan - 5 Jan
Big Bears Lodge
Front of property
Stay At Jimmy's

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (46)
"Very cool vibe at this very comfortable B&B. Hosts were very friendly and responsive. Would definitely stay here again!"
United States
Thomas
The price is AED 915
AED 1,006 total
includes taxes & fees
4 Jan - 5 Jan
Stay At Jimmy's
Exterior
Inn on Putney Road

Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (56)
"wonderful atmosphere, great breakfast, friedly staff, great location"
United States
Kurt
The price is AED 862
AED 948 total
includes taxes & fees
4 Jan - 5 Jan
Inn on Putney Road
Economy Room | Individually decorated, individually furnished, free WiFi, bed sheets
The Vesper

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (52)
"Charming bed and breakfast"
United States
Nicholas
The price is AED 614
AED 675 total
includes taxes & fees
11 Jan - 12 Jan
The Vesper
Property grounds
Room 7 - family room sleeps 4

Room 7 - family room sleeps 4

Room 7 - family room sleeps 4
Manchester
10.0 out of 10, Exceptional, (1)
"Nice spot, good location. Towels could be better, but overall a great spot. "
United States
Kuan-Chung
The price is AED 289
AED 502 total
includes taxes & fees
4 Jan - 5 Jan
Room 7 - family room sleeps 4
Front of property
The Inn at Ormsby Hill

The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (150)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
The price is AED 1,061
AED 1,168 total
includes taxes & fees
4 Jan - 5 Jan
The Inn at Ormsby Hill
Lobby
Chesterfield Inn

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104)
"Great stay"
United States
Wayne
The price is AED 1,129
AED 1,225 total
includes taxes & fees
13 Jan - 14 Jan
Chesterfield Inn
Exterior
Deerfield Valley Inn

Deerfield Valley Inn

Deerfield Valley Inn
3.0 star property
West Dover
9.6 out of 10, Exceptional, (90)
"Staff was great and the location is very close to the ski area. Cozy atmosphere at hotel."
Canada
Shane
Deerfield Valley Inn
Outdoor pool
Echo Lake Inn

Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (98)
"No lake-view. Friendly staff, excellent breakfast."
United States
Wendy
The price is AED 985
AED 1,073 total
includes taxes & fees
5 Jan - 6 Jan
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 Jackson

The Jackson

10/10 Excellent
"The most beautiful stay during Christmastime. The inn is absolutely stunning and cozy, designed with the most thoughtful detail and rare antiques everywhere."
Rachael 1-night trip
Posted 1 day ago
The Jackson

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?
Check out this B&B in the surrounding area: 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.