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Check prices for these dates

Next weekend
Feb 20 - Feb 22
In two weeks
Feb 27 - Mar 1
In one month
Mar 13 - Mar 15
In two months
Apr 10 - Apr 12

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, (112 reviews)
"So great all around!"
United States
Janet
The price is ₩301,077
₩328,173 total
includes taxes & fees
Feb 24 - Feb 25
Stone Hearth Inn and Eatery
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (21 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, (78 reviews)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is ₩216,573
₩238,230 total
includes taxes & fees
Feb 17 - Feb 18
The One Cat B&B
Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (249 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, (167 reviews)
"Very helpful and welcoming host. "
United States
Bruce
The price is ₩220,245
₩238,966 total
includes taxes & fees
Feb 22 - Feb 23
The Carriage Barn 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, (344 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is ₩227,017
₩249,733 total
includes taxes & fees
Feb 25 - Feb 26
Colonel Williams Inn
Lounge

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (422 reviews)
"Clean room/ great breakfast"
United States
Ryan
Bromley View Inn
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, (114 reviews)
"Host was wonderful. "
United States
Robert
The price is ₩258,007
₩283,808 total
includes taxes & fees
Feb 22 - Feb 23
Blue Gentian Lodge at Magic Mountain
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.8 out of 10, Exceptional, (266 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
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (55 reviews)
"Charming bed and breakfast"
United States
Nicholas
The price is ₩267,549
₩294,315 total
includes taxes & fees
Feb 16 - Feb 17
The Vesper
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 ₩338,148
₩371,963 total
includes taxes & fees
Feb 16 - Feb 17
Inn on Putney Road
Exterior

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (288 reviews)
"super cute and clean, felt like home after not living there for 4 years!"
United States
MacLean
The price is ₩238,230
₩262,053 total
includes taxes & fees
Mar 1 - Mar 2
The Inn at Manchester
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
The price is ₩338,724
₩372,597 total
includes taxes & fees
Mar 3 - Mar 4
Deer Brook Inn
Garden

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (199 reviews)
"Great mom and pop motel minutes from Mount Snow"
United States
Richard
The price is ₩256,926
₩282,611 total
includes taxes & fees
Feb 24 - Feb 25
Big Bears Lodge
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 ₩272,421
₩296,939 total
includes taxes & fees
Feb 24 - Feb 25
Windham Hill Inn
Front of property

Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (47 reviews)
"Wonderful amenities, location, and team, Highly recommend and would love to stay again"
United States
Heather
The price is ₩430,973
₩474,071 total
includes taxes & fees
Feb 18 - Feb 19
Stay At Jimmy's
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
3.0 star property
West Dover
9.4 out of 10, Exceptional, (106 reviews)
"Great location Host Oz cooked up a great breakfast Room was fine for one person "
United States
michael
Deerfield Valley Inn
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, (154 reviews)
"Love this place! Have stayed here twice now and will again. Great location, beautiful rooms, delicious breakfast and very friendly owners. A+"
United States
cynthia
The price is ₩330,076
₩363,084 total
includes taxes & fees
Feb 25 - Feb 26
The Inn at Ormsby Hill
Front of property - evening/night

Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.0 out of 10, Wonderful, (104 reviews)
"Great stay"
United States
Wayne
The price is ₩443,138
₩480,801 total
includes taxes & fees
Feb 24 - Feb 25
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

On The River Inn

On The River Inn

10/10 Excellent
"The room was clean and the kitchen area was well stocked. The staff is always extremely friendly and helpful. The only thing about the room that could use updating was the carpeting. It was frayed in spots and looked like it needed a refresh!"
Mona 2-night trip
Posted 2 days ago
On The River Inn

Find out more about Chester

Chester B&B information

Number of reviews
2,709
Accommodation
34 B&B
Lowest Price
₩238,230
Highest Price
₩480,801

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 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. Situated 17.8 mi (28.6 km) from the heart of Chester. 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 Okemo 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.

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