A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

Find the Best Chester Bed and Breakfast

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept
In one month
2 Oct - 4 Oct
In two months
30 Oct - 1 Nov

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, (123 reviews)
"We had a lovely stay at Stone Hearth Inn! Very quaint place and comfortable, clean accommodations. Beautiful grounds around the property with outside seating to enjoy the fresh air. The dinner we had at the attached “Eatery” was awesome!!! So was the amazingly delicious included breakfast. Vickie was so welcoming and kind. We can’t say enough good things! Highly recommend"
United States
Kathleen
The price is £163
includes taxes & fees
1 Sept - 2 Sept
Stone Hearth Inn and Eatery
A calm lake reflecting a forest with autumn foliage.

2. Blue Gentian Lodge at Magic Mountain

Blue Gentian Lodge at Magic Mountain
2.5 star property
Londonderry
9.2 out of 10, Wonderful, (123 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
The price is £121
includes taxes & fees
1 Sept - 2 Sept
Blue Gentian Lodge at Magic Mountain
A cozy room with a fireplace, green sofas, a pool table, and a lamp.

3. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (474 reviews)
"Pleasant stay - excellent breakfast!"
Canada
William
The price is £62
includes taxes & fees
1 Sept - 2 Sept
Bromley View Inn
A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

4. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (277 reviews)
"Beautiful views of the river excellent breakfast"
United States
Michael
The price is £129
includes taxes & fees
2 Sept - 3 Sept
Harvest Barn Inn
A wooden deck with a solar panel, surrounded by lush greenery and a hill in the background.

5. Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (44 reviews)
"The view of mountains id stunning, as is the aroma of fresh air and the enchanting songbirds. We had a great time in the small but adequate swimming pool. It is easy to miss the turn onto Laurence Lane, so it would be good if a sign were to be installed there."
United States
Nadine
The price is £188
includes taxes & fees
22 Sept - 23 Sept
Windham Hill Inn
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

6. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (54 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
The price is £113
includes taxes & fees
9 Sept - 10 Sept
Four Columns Inn
A large, multi-story building with a symmetrical facade, multiple windows, and a balcony with railings.

7. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.6 out of 10, Excellent, (102 reviews)
"Kat and everyone were very friendly and helpful, we had a wonderful stay"
United States
Michael
The price is £169
includes taxes & fees
2 Sept - 3 Sept
Echo Lake Inn
A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.

8. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (310 reviews)
"Everything was terrific! Great vibe & location."
United States
Brian
The price is £145
includes taxes & fees
1 Sept - 2 Sept
The Jackson
A large red barn and a white house with a porch, surrounded by trees and a well-maintained lawn.

9. The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (373 reviews)
"Great staff, great location and beautiful place!"
United States
Lori
The price is £130
includes taxes & fees
9 Sept - 10 Sept
The Inn at Manchester

10. Doveberry Inn

Doveberry Inn
2.0 star property
West Dover
The price is £119
includes taxes & fees
8 Sept - 9 Sept
Doveberry Inn
A large white building with a stone wall and a lawn covered in fallen leaves.

11. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (358 reviews)
"A very historic and well maintained bed and breakfast. The owners are wonderful and the rooms were cozy. The hand made breakfast was a highlight"
United States
Robert
The price is £128
includes taxes & fees
1 Sept - 2 Sept
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, (74 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
The price is £142
includes taxes & fees
7 Sept - 8 Sept
The Vesper
A wooden table set with plates, cutlery, and a folded napkin.

13. The Carriage Barn Inn

The Carriage Barn Inn
3.0 star property
Keene
9.6 out of 10, Exceptional, (176 reviews)
"Perfectly clean and quaint. Friendly owner, great location"
United States
Jonathan
The price is £121
includes taxes & fees
9 Sept - 10 Sept
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, (7 reviews)
"Everything was fantastic, my room and the staff."
United States
Laurence
The price is £187
includes taxes & fees
1 Sept - 2 Sept
Deer Brook Inn
A row of cabins with a snow-covered ground and trees in the background.

15. Sleep Woodstock - Dog Friendly King Suite

Sleep Woodstock - Dog Friendly King Suite
Woodstock
10.0 out of 10, Exceptional, (1 review)
"Considering the place was hit by a TORNADO the week prior to our visit, the accommodations were great, and the owner/host was in remarkably good spirits despite hassles with insurance."
United States
David M.
The price is £123
includes taxes & fees
7 Sept - 8 Sept
Sleep Woodstock - Dog Friendly King Suite
A stone fire pit surrounded by rocks, with a tree in the background and a building with a red roof to the left.

16. Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (132 reviews)
"Good price, really quite, clean, person on site very friendly helpful with places we can go & things to do I recommend the place"
United States
Patrick
The price is £92
includes taxes & fees
15 Sept - 16 Sept
Deerfield Valley Inn
A two-story house with a covered patio area, a small outdoor seating area, and a gravel driveway.

17. Room 1, peaceful retreat in Manchester - King bed

Room 1, peaceful retreat in Manchester - King bed
Manchester
10.0 out of 10, Exceptional, (2 reviews)
"Cute little motel. Place was clean and the host was very helpful with any questions I had. The fire area was nice to go relax at the end of the day. Highly recommended a visit if your in the at area."
United States
Ivy B.
The price is £112
includes taxes & fees
1 Sept - 2 Sept
Room 1, peaceful retreat in Manchester - King bed
A porch with wicker chairs, potted plants, and a number '43' sign.

18. The One Cat B&B

The One Cat B&B
2.5 star property
Brattleboro
9.8 out of 10, Exceptional, (81 reviews)
"Breakfast was fantastic Did not need any shops Hosts were super friendly We enjoyed our short stay"
United States
marjie
The price is £229
includes taxes & fees
1 Oct - 2 Oct
The One Cat B&B
A house with a red roof, a porch with white railings, and a blue door.

19. Woodbridge Inn

Woodbridge Inn
3.0 star property
Woodstock
9.6 out of 10, Exceptional, (67 reviews)
"Great place to stay"
United States
eric
The price is £402
includes taxes & fees
7 Sept - 8 Sept
Woodbridge Inn
A garden with a large rock centerpiece, surrounded by various plants and a wooden structure in the background.

20. Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (216 reviews)
"Clean and convenient, would stay again. "
United States
Todd
The price is £140
includes taxes & fees
1 Sept - 2 Sept
Big Bears Lodge
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

Latchis Hotel

Latchis Hotel

10/10 Excellent
"Clean room, it is an older place but very nice. Only issue was a shortage of electrical outlets in room. We needed to unplug lamps in order to plug in phone chargers. No outlets for hair dryer near a mirror. But all part of the ambience."
Linda 3-night trip
Posted 2 hours ago
Latchis Hotel

Find out more about Chester

Chester B&B information

Number of reviews
2,054
Accommodation
66 B&B
Lowest Price
£62
Highest Price
£402

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.

Explore a world of travel with Expedia