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Check prices for these dates

Next weekend
15 May - 17 May
In two weeks
22 May - 24 May
In one month
5 Jun - 7 Jun
In two months
3 Jul - 5 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 AED 698
AED 761 total
includes taxes & fees
26 May - 27 May
Stone Hearth Inn and Eatery
Lounge

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (441 reviews)
"We had an enjoyable stay and would stay again. "
United States
Donna
The price is AED 293
AED 322 total
includes taxes & fees
11 May - 12 May
Bromley View Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (36 reviews)
"The hot tub was so amazing"
United States
Mark
The price is AED 479
AED 522 total
includes taxes & fees
11 May - 12 May
Four Columns Inn
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (353 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is AED 532
AED 585 total
includes taxes & fees
21 May - 22 May
Colonel Williams Inn
Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (262 reviews)
"If you're planning a trip to bellows falls or the surrounding areas I would highly recommend the Harvest Barn Inn. The location is beauti"
United States
Gabriel
The price is AED 547
AED 596 total
includes taxes & fees
17 May - 18 May
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 AED 625
AED 678 total
includes taxes & fees
11 May - 12 May
The Carriage Barn Inn
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.4 out of 10, Exceptional, (60 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 AED 574
AED 631 total
includes taxes & fees
12 May - 13 May
The Vesper
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (279 reviews)
"Easy Check-In; Lovely Room; Great Location & Atmosphere. The staff was very friendly,"
United States
Michael
The price is AED 548
AED 603 total
includes taxes & fees
8 Jun - 9 Jun
The Jackson
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 AED 905
AED 995 total
includes taxes & fees
12 May - 13 May
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, (118 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
The price is AED 536
AED 590 total
includes taxes & fees
28 May - 29 May
Blue Gentian Lodge at Magic Mountain
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (118 reviews)
"Great location Host Oz cooked up a great breakfast Room was fine for one person "
United States
michael
The price is AED 294
AED 425 total
includes taxes & fees
27 May - 28 May
Deerfield Valley 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, (311 reviews)
"Staff was exceptionally friendly…lovely Inn! Beautiful views "
United States
Michael
The price is AED 606
AED 667 total
includes taxes & fees
31 May - 1 Jun
The Inn at Manchester
Exterior

Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AED 270
AED 461 total
includes taxes & fees
11 May - 12 May
Sleep Woodstock - 2 Double Beds - Dog Friendly
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 AED 683
AED 744 total
includes taxes & fees
27 May - 28 May
Windham Hill 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 AED 270
AED 461 total
includes taxes & fees
10 May - 11 May
Room 7 - family room sleeps 4
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 AED 846
AED 931 total
includes taxes & fees
13 May - 14 May
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 AED 779
AED 849 total
includes taxes & fees
25 May - 26 May
Echo Lake Inn
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 AED 1,043
AED 1,148 total
includes taxes & fees
21 May - 22 May
Inn on Putney Road
Garden

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (214 reviews)
"Great mom and pop motel minutes from Mount Snow"
United States
Richard
The price is AED 634
AED 697 total
includes taxes & fees
22 May - 23 May
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, (161 reviews)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
The price is AED 951
AED 1,046 total
includes taxes & fees
10 May - 11 May
The Inn at Ormsby Hill
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

Latchis Hotel

Latchis Hotel

10/10 Excellent
"Really great place to stay in Brattleboro. Clean room, friendly and helpful staff, free coffee in the lobby and a great little bar/restaurant is attached. I'll definitely be back."
Kaitlin 3-night trip
Posted 10 hours ago
Latchis Hotel

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?
This is a B&B that Expedia travelers like in Chester: Stone Hearth Inn and Eatery: 8 rooms. Enjoy the free buffet breakfast and unique décor.
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 North Springfield Lake Recreation Area 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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