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Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13

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 CA $252
CA $275 total
includes taxes & fees
Nov 16 - Nov 17
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, (126 reviews)
"Lovely stay near Magic Mountain. "
United States
Abigail
The price is CA $180
CA $198 total
includes taxes & fees
Nov 8 - Nov 9
Blue Gentian Lodge at Magic Mountain
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, (292 reviews)
"The breakfasts were amazing and the hosts were super kind and helpful!"
United States
gail
The price is CA $195
CA $212 total
includes taxes & fees
Nov 2 - Nov 3
Harvest Barn Inn
A cozy room with a fireplace, green sofas, a pool table, and a lamp.

4. Bromley View Inn

Bromley View Inn
3.5 star property
Bondville
9.0 out of 10, Wonderful, (496 reviews)
"Great amenities, fantastic views, very clean, excellent breakfast!"
United States
BARBARA
The price is CA $109
CA $120 total
includes taxes & fees
Nov 1 - Nov 2
Bromley View Inn
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

5. Four Columns Inn

Four Columns Inn
4.0 star property
Newfane
9.8 out of 10, Exceptional, (61 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
The price is CA $135
CA $148 total
includes taxes & fees
Nov 2 - Nov 3
Four Columns Inn
A wooden deck with a solar panel, surrounded by lush greenery and a hill in the background.

6. Windham Hill Inn

Windham Hill Inn
4.0 star property
West Townshend
8.6 out of 10, Excellent, (47 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 $251
CA $273 total
includes taxes & fees
Oct 28 - Oct 29
Windham Hill Inn
A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.

7. The Jackson

The Jackson
4.0 star property
West Woodstock
9.6 out of 10, Exceptional, (331 reviews)
"Amazing stay and great restaurant!"
United States
Ava
The price is CA $175
CA $192 total
includes taxes & fees
Nov 16 - Nov 17
The Jackson
A stone fire pit surrounded by rocks, with a tree in the background and a building with a red roof to the left.

8. Deerfield Valley Inn

Deerfield Valley Inn
2.0 star property
West Dover
9.4 out of 10, Exceptional, (134 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 $65
CA $111 total
includes taxes & fees
Nov 16 - Nov 17
Deerfield Valley Inn
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, (392 reviews)
"Amazing place in a beautiful setting!"
United States
Dawn
The price is CA $198
CA $250 total
includes taxes & fees
Nov 16 - Nov 17
The Inn at Manchester
A bedroom with a bed, dresser, TV, and a chair.

10. 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 CA $157
CA $173 total
includes taxes & fees
Oct 25 - Oct 26
Doveberry Inn
A living room with a grey sectional sofa, a potted plant, and a radiator.

11. The Vesper

The Vesper
3.0 star property
Woodstock
9.2 out of 10, Wonderful, (80 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
The price is CA $234
CA $258 total
includes taxes & fees
Nov 15 - Nov 16
The Vesper
A cozy living room with a fireplace, wicker chairs, and a coffee table with snacks.

12. 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 $330
CA $363 total
includes taxes & fees
Nov 16 - Nov 17
Deer Brook Inn
A large white building with a stone wall and a lawn covered in fallen leaves.

13. Colonel Williams Inn

Colonel Williams Inn
3.0 star property
Brattleboro
9.8 out of 10, Exceptional, (362 reviews)
"Beautiful grounds, nice walking trails, comfortable bed, excellent breakfast."
United States
Amy
The price is CA $206
CA $227 total
includes taxes & fees
Nov 3 - Nov 4
Colonel Williams Inn
A wooden table set with plates, cutlery, and a folded napkin.

14. 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 CA $199
CA $216 total
includes taxes & fees
Oct 19 - Oct 20
The Carriage Barn Inn
A garden with a large rock centerpiece, surrounded by various plants and a wooden structure in the background.

15. Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (220 reviews)
"Welcoming host with great customer service"
United States
Alfred
The price is CA $245
CA $269 total
includes taxes & fees
Oct 28 - Oct 29
Big Bears Lodge
A row of cabins with a snow-covered ground and trees in the background.

16. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is CA $148
CA $249 total
includes taxes & fees
Nov 16 - Nov 17
Sleep Woodstock - 2 Double Beds - Dog Friendly
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 $112
CA $210 total
includes taxes & fees
Nov 16 - Nov 17
Room 1, peaceful retreat in Manchester - King bed
A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.

18. 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 CA $379
CA $417 total
includes taxes & fees
Nov 15 - Nov 16
Inn on Putney Road
A two-story house with a snow-covered roof and yard, featuring multiple lit windows and a visible chimney.

19. 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 CA $365
CA $401 total
includes taxes & fees
Nov 15 - Nov 16
The Inn at Ormsby Hill
A modern fitness center with exercise equipment, mirrors, and a reception area.

20. Stay At Jimmy's

Stay At Jimmy's
3.0 star property
Woodstock
10.0 out of 10, Exceptional, (54 reviews)
"My husband kept saying that the room was a model for providing everything a traveler might need. Lovely stay."
United States
Jeanne
The price is CA $424
CA $467 total
includes taxes & fees
Oct 29 - Oct 30
Stay At Jimmy's
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
"Very nice hotel! Recommend"
Vladimir 1-night trip
Posted 1 hour ago
Hampton Inn and Suites Manchester

Find out more about Chester

Chester B&B information

Number of reviews
2,494
Accommodation
65 B&B
Lowest Price
CA $111
Highest Price
CA $467

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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