Search B&B in Chester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
17 Apr - 19 Apr
In two weeks
24 Apr - 26 Apr
In one month
8 May - 10 May
In two months
5 Jun - 7 Jun

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 Rp3.572.700
Rp3.894.243 total
includes taxes & fees
13 Apr - 14 Apr
Stone Hearth Inn and Eatery
Lounge

Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (438 reviews)
"We had an enjoyable stay and would stay again. "
United States
Donna
The price is Rp1.362.334
Rp1.498.652 total
includes taxes & fees
13 Apr - 14 Apr
Bromley View Inn
Porch

Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (257 reviews)
"Staff were wonderful, food was excellent, environment was peaceful, everything was clean and in decent condition."
United States
Charles
The price is Rp2.580.651
Rp2.812.910 total
includes taxes & fees
13 Apr - 14 Apr
Harvest Barn Inn
Land view from property

Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful location and nice staff."
United States
Cynthia
The price is Rp2.232.072
Rp2.432.959 total
includes taxes & fees
13 Apr - 14 Apr
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, (171 reviews)
"Super cute property. Rooms are clean with historical "
United States
Valerie
The price is Rp2.593.822
Rp2.814.297 total
includes taxes & fees
13 Apr - 14 Apr
The Carriage Barn Inn
Exterior

Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (115 reviews)
"Great location Host Oz cooked up a great breakfast Room was fine for one person "
United States
michael
The price is Rp1.370.030
Rp1.977.392 total
includes taxes & fees
14 Apr - 15 Apr
Deerfield Valley Inn
Front of property

Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (350 reviews)
"The hotel was very clean, the staff were friendly and welcoming, and the breakfast was delicious."
United States
Sahand
The price is Rp2.693.880
Rp2.963.439 total
includes taxes & fees
26 Apr - 27 Apr
Colonel Williams Inn
Interior

The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (57 reviews)
"Uniqueness of rooms, breakfast options and walking distance to so many great spots!"
United States
Emily
The price is Rp2.405.164
Rp2.645.818 total
includes taxes & fees
15 Apr - 16 Apr
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, (79 reviews)
"Conrad and Pat were so welcoming, their house was adorable, and breakfast was superb!"
United States
Cara
The price is Rp4.276.000
Rp4.703.600 total
includes taxes & fees
18 Apr - 19 Apr
The One Cat B&B
Restaurant

The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (277 reviews)
"Easy Check-In; Lovely Room; Great Location & Atmosphere. The staff was very friendly,"
United States
Michael
The price is Rp3.270.285
Rp3.597.313 total
includes taxes & fees
6 May - 7 May
The Jackson
Property grounds

The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (306 reviews)
"Staff was exceptionally friendly…lovely Inn! Beautiful views "
United States
Michael
The price is Rp3.164.240
Rp3.480.664 total
includes taxes & fees
30 Apr - 1 May
The Inn at Manchester
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 Rp3.232.656
Rp3.523.595 total
includes taxes & fees
23 Apr - 24 Apr
Windham Hill Inn
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 Rp4.268.303
Rp4.695.219 total
includes taxes & fees
13 Apr - 14 Apr
Inn on Putney Road
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, (160 reviews)
"Lovely place to stay Jack and Maryann excellent hosts"
United States
Lenny
The price is Rp4.429.936
Rp4.872.929 total
includes taxes & fees
13 Apr - 14 Apr
The Inn at Ormsby Hill
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 Rp4.421.384
Rp4.863.521 total
includes taxes & fees
13 Apr - 14 Apr
Deer Brook Inn
Garden

Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (210 reviews)
"Great mom and pop motel minutes from Mount Snow"
United States
Richard
The price is Rp2.950.440
Rp3.245.655 total
includes taxes & fees
13 Apr - 14 Apr
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 Rp5.150.699
Rp5.588.561 total
includes taxes & fees
19 Apr - 20 Apr
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Hampton Inn Brattleboro

Hampton Inn Brattleboro

8/10 Good
"The breakfast was not very good. "
Becky 1-night trip
Posted 3 hours ago
Hampton Inn Brattleboro

Find out more about Chester

Chester B&B information

Number of reviews
2,153
Accommodation
32 B&B
Lowest Price
Rp1.498.652
Highest Price
Rp5.588.561

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, DaVallia Art & Accents and Bonnie's Bundles Dolls 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 well-liked 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 decor. Bromley View Inn: 16 rooms. Located 17.8 mi (28.6 km) from the core 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 DaVallia Art & Accents and Bonnie's Bundles Dolls. You might also consider a trip to sites such as 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 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.

Explore a world of travel with Expedia