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
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for Chester bed & breakfast

A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

1. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
3.0 star property
Chester
9.2 out of 10, Wonderful, (130 reviews)
"Wonderful staff and restaurant"
United States
John
The price is RM846
RM922 total
includes taxes & fees
16 Nov - 17 Nov
Stone Hearth Inn and Eatery
A cozy room with a fireplace, green sofas, a pool table, and a lamp.

2. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (503 reviews)
"Great amenities, fantastic views, very clean, excellent breakfast!"
United States
BARBARA
The price is RM335
RM369 total
includes taxes & fees
22 Nov - 23 Nov
Bromley View Inn
A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

3. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (296 reviews)
"Staff was excellent and river views were amazing"
United States
John
The price is RM658
RM717 total
includes taxes & fees
28 Nov - 29 Nov
Harvest Barn Inn
A snow-covered cabin with a large window, surrounded by trees and a mountain in the background.

4. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (126 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
The price is RM603
RM664 total
includes taxes & fees
10 Nov - 11 Nov
Blue Gentian Lodge at Magic Mountain
A stone fire pit surrounded by rocks, with a tree in the background and a building with a red roof to the left.

5. Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (140 reviews)
"A very quaint, cozy inn set in West Dover, Vermont. We had a small room but it was clean and comfortable. We didn't choose to order breakfast while we were there but it smelled wonderful! Oz, the host, was professional, pleasant, and helpful."
United States
Ted
The price is RM186
RM316 total
includes taxes & fees
22 Nov - 23 Nov
Deerfield Valley Inn
A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.

6. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (338 reviews)
"Amazing stay and great restaurant!"
United States
Ava
The price is RM499
RM549 total
includes taxes & fees
11 Nov - 12 Nov
The Jackson
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

7. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (63 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
The price is RM634
RM691 total
includes taxes & fees
8 Nov - 9 Nov
Four Columns Inn
A two-story building with a blue exterior, a wooden front porch, and a sign indicating a vacancy.

8. Doveberry Inn

Doveberry Inn
3.0 star property
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Great location… very clean"
United States
Veronica
The price is RM547
RM601 total
includes taxes & fees
8 Nov - 9 Nov
Doveberry Inn
A large, multi-story building with a symmetrical facade, multiple windows, and a balcony with railings.

9. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
9.0 out of 10, Wonderful, (108 reviews)
"Beautiful location and all was well"
United States
richard
The price is RM1,328
RM1,448 total
includes taxes & fees
25 Nov - 26 Nov
Echo Lake Inn
A large, snow-covered house with multiple windows and a well-lit porch.

10. The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (401 reviews)
"Great place. Great host!"
United States
Zhihao
The price is RM565
RM715 total
includes taxes & fees
8 Nov - 9 Nov
The Inn at Manchester
A room with two single beds, a desk, and a radiator.

11. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (363 reviews)
"Beautiful grounds, nice walking trails, comfortable bed, excellent breakfast."
United States
Amy
The price is RM723
RM795 total
includes taxes & fees
8 Nov - 9 Nov
Colonel Williams Inn
A living room with a grey sectional sofa, a potted plant, and a radiator.

12. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (85 reviews)
"Very cute spot, good location and staff is super nice:)"
Canada
Rhea
The price is RM668
RM735 total
includes taxes & fees
12 Nov - 13 Nov
The Vesper
A dining area with wooden tables and chairs, large windows with a view of trees, and a bench along the wall.

13. The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (177 reviews)
"Clean,quiet, beautiful inn in the heart of downtown Keene,NH. Joe was friendly and accommodating and a hell of a great guy. A+++++++"
United States
Richard
The price is RM546
RM592 total
includes taxes & fees
18 Nov - 19 Nov
The Carriage Barn Inn
A cozy living room with a fireplace, wicker chairs, and a coffee table with snacks.

14. Deer Brook Inn

Deer Brook Inn
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (10 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
The price is RM942
RM1,036 total
includes taxes & fees
9 Nov - 10 Nov
Deer Brook Inn
A sign for Big Bear's Lodge advertising a heated pool, hot tub, and free WiFi.

15. Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (222 reviews)
"Welcoming host with great customer service"
United States
Alfred
The price is RM699
RM768 total
includes taxes & fees
29 Nov - 30 Nov
Big Bears Lodge
A two-story house with a snow-covered roof and yard, featuring multiple lit windows and a visible chimney.

16. The Inn at Ormsby Hill

The Inn at Ormsby Hill
3.5 star property
Manchester Center
9.8 out of 10, Exceptional, (172 reviews)
"It is a wonderful property inside and out. Great rooms, breakfasts and and very friendly people."
United States
Victoria
The price is RM927
RM1,020 total
includes taxes & fees
10 Nov - 11 Nov
The Inn at Ormsby Hill
A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.

17. Inn on Putney Road

Inn on Putney Road
4.0 star property
Brattleboro
9.8 out of 10, Exceptional, (61 reviews)
"Helpful staff, wonderful breakfast and homey ambiance."
United States
Karla
The price is RM1,081
RM1,189 total
includes taxes & fees
10 Nov - 11 Nov
Inn on Putney Road
A large, two-story house with a snow-covered driveway and surrounding trees.

18. Chesterfield Inn

Chesterfield Inn
4.0 star property
West Chesterfield
9.4 out of 10, Exceptional, (106 reviews)
"Great stay"
United States
Wayne
The price is RM1,219
RM1,323 total
includes taxes & fees
15 Nov - 16 Nov
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

Learn more about Chester

Nestled in a relaxing small-town setting, Chester invites visitors to explore DaVallia Art & Accents and browse handcrafted treasures at Bonnie's Bundles Dolls. Outdoor enthusiasts can enjoy nearby Stoughton Pond Recreation Area or take a scenic drive to Lowell Lake State Park and the charming Vermont Country Store.

See all hotels in Chester
A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

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 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 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.