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

Find a Bed and Breakfast in Chester from CA $117

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Check prices for these dates

Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13
In one month
Sep 25 - Sep 27
In two months
Oct 23 - Oct 25

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, (122 reviews)
"Great stay! Very cozy and homey. Very yummy breakfast! "
United States
Olena
The price is CA $241
CA $263 total
includes taxes & fees
Aug 31 - Sep 1
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 CA $207
CA $228 total
includes taxes & fees
Aug 31 - Sep 1
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, (472 reviews)
"Pleasant stay - excellent breakfast!"
Canada
William
The price is CA $106
CA $117 total
includes taxes & fees
Aug 31 - Sep 1
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, (275 reviews)
"Beautiful views of the river excellent breakfast"
United States
Michael
The price is CA $218
CA $237 total
includes taxes & fees
Sep 1 - Sep 2
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 CA $258
CA $282 total
includes taxes & fees
Sep 9 - Sep 10
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)
"Can’t go wrong with this place."
United States
John
The price is CA $196
CA $214 total
includes taxes & fees
Sep 1 - Sep 2
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 CA $292
CA $318 total
includes taxes & fees
Sep 7 - Sep 8
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, (307 reviews)
"Everything was terrific! Great vibe & location."
United States
Brian
The price is CA $249
CA $274 total
includes taxes & fees
Aug 31 - Sep 1
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 CA $194
CA $245 total
includes taxes & fees
Sep 9 - Sep 10
The Inn at Manchester

10. Doveberry Inn

Doveberry Inn
2.0 star property
West Dover
The price is CA $203
CA $223 total
includes taxes & fees
Aug 31 - Sep 1
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 CA $207
CA $227 total
includes taxes & fees
Sep 1 - Sep 2
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 CA $243
CA $268 total
includes taxes & fees
Aug 31 - Sep 1
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 CA $185
CA $201 total
includes taxes & fees
Aug 31 - Sep 1
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 CA $320
CA $352 total
includes taxes & fees
Aug 31 - Sep 1
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 CA $128
CA $226 total
includes taxes & fees
Sep 14 - Sep 15
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 CA $122
CA $173 total
includes taxes & fees
Sep 13 - Sep 14
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 CA $120
CA $217 total
includes taxes & fees
Sep 1 - Sep 2
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 CA $344
CA $379 total
includes taxes & fees
Aug 31 - Sep 1
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 CA $688
CA $757 total
includes taxes & fees
Sep 7 - Sep 8
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 CA $240
CA $264 total
includes taxes & fees
Aug 31 - Sep 1
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.
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Top Chester Hotel Reviews

The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

10/10 Excellent
"Nice room and property. With was down."
Amanda 1-night trip
Posted 3 hours ago
The Palmer House Resort, an Ascend Collection Hotel

Find out more about Chester

Chester B&B information

Number of reviews
2,472
Accommodation
65 B&B
Lowest Price
CA $117
Highest Price
CA $757

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, DaVallia Art & Accents and Bonnie's Bundles Dolls 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 DaVallia Art & Accents and Bonnie's Bundles Dolls. You might also consider a trip to sites like 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 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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