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Check prices for these dates

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

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 S$262
includes taxes & fees
2 Mar - 3 Mar
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 S$200
includes taxes & fees
19 Feb - 20 Feb
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 S$209
includes taxes & fees
18 Feb - 19 Feb
The Carriage Barn Inn
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 S$199
includes taxes & fees
25 Feb - 26 Feb
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 S$239
includes taxes & fees
22 Feb - 23 Feb
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 S$238
includes taxes & fees
1 Mar - 2 Mar
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 S$326
includes taxes & fees
16 Feb - 17 Feb
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 S$229
includes taxes & fees
17 Mar - 18 Mar
The Inn at Manchester
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
The price is S$317
includes taxes & fees
9 Mar - 10 Mar
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 S$247
includes taxes & fees
25 Feb - 26 Feb
Big Bears Lodge
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 S$247
includes taxes & fees
18 Feb - 19 Feb
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 S$415
includes taxes & fees
16 Feb - 17 Feb
Stay At Jimmy's
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
3.0 star property
West Dover
9.4 out of 10, Exceptional, (105 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 S$318
includes taxes & fees
19 Feb - 20 Feb
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 S$421
includes taxes & fees
16 Feb - 17 Feb
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

Fullerton Inn

Fullerton Inn

10/10 Excellent
"Friendliness, ease of checkin and iut"
Marguerite 1-night trip
Posted 9 hours ago
Fullerton Inn

Find out more about Chester

Chester B&B information

Number of reviews
2,706
Accommodation
34 B&B
Lowest Price
S$199
Highest Price
S$421

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, Bonnie's Bundles Dolls and DaVallia Art & Accents 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?
Here are some B&Bs in the surrounding 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 decor. Bromley View Inn: 16 rooms. Situated 17.8 mi (28.6 km) from the heart of Chester. Enjoy the unique decor and fireplace in reception.
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 Bonnie's Bundles Dolls and DaVallia Art & Accents. You might also consider a trip to sites such as 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 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.

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