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Check prices for these dates

Next weekend
Feb 27 - Mar 1
In two weeks
Mar 6 - Mar 8
In one month
Mar 20 - Mar 22
In two months
Apr 17 - Apr 19

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 P12,086
P13,174 total
includes taxes & fees
Mar 4 - Mar 5
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
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
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 P8,679
P9,547 total
includes taxes & fees
Feb 22 - Feb 23
The One Cat B&B
Free daily continental breakfast

The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (168 reviews)
"Very helpful and welcoming host. "
United States
Bruce
The price is P8,841
P9,593 total
includes taxes & fees
Feb 22 - Feb 23
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, (346 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is P9,113
P10,025 total
includes taxes & fees
Feb 22 - Feb 23
Colonel Williams Inn
Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (251 reviews)
"Everything was great. Awesome hosts, room, common areas and a fabulous breakfast. Can’t recommend too highly."
United States
Mark
Harvest Barn 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 P10,357
P11,393 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
9.6 out of 10, Exceptional, (270 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, (56 reviews)
"Charming bed and breakfast"
United States
Nicholas
The price is P9,764
P10,741 total
includes taxes & fees
Feb 22 - Feb 23
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 P13,574
P14,932 total
includes taxes & fees
Mar 5 - Mar 6
Inn on Putney Road
Interior

Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
The price is P13,598
P14,957 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, (200 reviews)
"Great mom and pop motel minutes from Mount Snow"
United States
Richard
The price is P10,314
P11,345 total
includes taxes & fees
Feb 23 - Feb 24
Big Bears Lodge
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 P9,547
P10,502 total
includes taxes & fees
Mar 1 - Mar 2
The Inn at Manchester
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 P10,936
P11,920 total
includes taxes & fees
Feb 26 - Feb 27
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 P17,301
P19,031 total
includes taxes & fees
Feb 22 - Feb 23
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, (155 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 P13,250
P14,575 total
includes taxes & fees
Mar 1 - Mar 2
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 P17,789
P19,301 total
includes taxes & fees
Feb 22 - Feb 23
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

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Clean, staff friendly "
Luigi 1-night trip
Posted 5 days ago
Hampton Inn and Suites Manchester

Find out more about Chester

Chester B&B information

Number of reviews
2,718
Accommodation
34 B&B
Lowest Price
P9,547
Highest Price
P19,301

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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