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Check prices for these dates

Next weekend
Jun 12 - Jun 14
In two weeks
Jun 19 - Jun 21
In one month
Jul 3 - Jul 5
In two months
Jul 31 - Aug 2

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 ₩317,085
₩345,623 total
includes taxes & fees
Jun 9 - Jun 10
Stone Hearth Inn and Eatery
Lounge

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (443 reviews)
"We had an enjoyable stay and would stay again. "
United States
Donna
The price is ₩128,971
₩141,874 total
includes taxes & fees
Jun 8 - Jun 9
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 ₩200,335
₩218,365 total
includes taxes & fees
Jun 8 - Jun 9
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, (172 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is ₩268,899
₩291,755 total
includes taxes & fees
Jun 9 - Jun 10
The Carriage Barn 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 ₩239,088
₩262,997 total
includes taxes & fees
Jun 9 - Jun 10
Colonel Williams Inn
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (283 reviews)
"Everything about our stay was perfect! Couldn't be happier and will be back!"
United States
Courtney
The price is ₩241,785
₩265,979 total
includes taxes & fees
Jun 9 - Jun 10
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 ₩263,953
₩287,709 total
includes taxes & fees
Jun 15 - Jun 16
Harvest Barn Inn
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 ₩121,594
₩175,501 total
includes taxes & fees
Jun 18 - Jun 19
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, (321 reviews)
"Had a wonderful stay. Staff very pleasant."
United States
Ellen
The price is ₩227,968
₩250,780 total
includes taxes & fees
Jun 22 - Jun 23
The Inn at Manchester
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 ₩265,654
₩292,219 total
includes taxes & fees
Jun 9 - Jun 10
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 ₩379,505
₩417,455 total
includes taxes & fees
Jun 6 - Jun 7
The One Cat B&B
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 ₩353,167
₩388,484 total
includes taxes & fees
Jun 29 - Jun 30
Deer Brook Inn
Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (49 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is ₩377,987
₩415,784 total
includes taxes & fees
Jun 16 - Jun 17
Stay At Jimmy's
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 ₩431,194
₩474,306 total
includes taxes & fees
Jun 9 - Jun 10
Inn on Putney Road
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 ₩349,888
₩381,378 total
includes taxes & fees
Jun 15 - Jun 16
Echo Lake Inn
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 ₩282,124
₩307,515 total
includes taxes & fees
Jun 15 - Jun 16
Windham Hill Inn
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 ₩261,858
₩288,059 total
includes taxes & fees
Jun 19 - Jun 20
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 ₩457,137
₩495,998 total
includes taxes & fees
Jun 9 - Jun 10
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

Latchis Hotel

Latchis Hotel

10/10 Excellent
"The front desk staff was courteous and the cheese platter at Sage was excellent."
Marcia 1-night trip
Posted 13 hours ago
Latchis Hotel

Find out more about Chester

Chester B&B information

Number of reviews
2,581
Accommodation
34 B&B
Lowest Price
₩141,874
Highest Price
₩495,998

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 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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