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Check prices for these dates

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

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 £164
includes taxes & fees
13 Nov - 14 Nov
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 £111
includes taxes & fees
4 Nov - 5 Nov
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 £111
includes taxes & fees
2 Nov - 3 Nov
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, (495 reviews)
"Great amenities, fantastic views, very clean, excellent breakfast!"
United States
BARBARA
The price is £64
includes taxes & fees
1 Nov - 2 Nov
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 £80
includes taxes & fees
3 Nov - 4 Nov
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 £146
includes taxes & fees
26 Oct - 27 Oct
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 £103
includes taxes & fees
3 Nov - 4 Nov
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 £59
includes taxes & fees
1 Nov - 2 Nov
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 £133
includes taxes & fees
5 Nov - 6 Nov
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 £101
includes taxes & fees
25 Oct - 26 Oct
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 £137
includes taxes & fees
9 Nov - 10 Nov
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 £194
includes taxes & fees
1 Nov - 2 Nov
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 £122
includes taxes & fees
20 Oct - 21 Oct
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 £112
includes taxes & fees
25 Oct - 26 Oct
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 £144
includes taxes & fees
28 Oct - 29 Oct
Big Bears Lodge
A wall with various framed artworks, including a collection of fishing floats and a colorful abstract painting.

16. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is £136
includes taxes & fees
9 Nov - 10 Nov
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 £115
includes taxes & fees
9 Nov - 10 Nov
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 £222
includes taxes & fees
5 Nov - 6 Nov
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 £214
includes taxes & fees
15 Nov - 16 Nov
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 £249
includes taxes & fees
29 Oct - 30 Oct
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

Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

10/10 Excellent
"This was a nice place. The staff was great as there were prompt responses to my inquiries. The property is a little dated but clean. We were not there long enough to enjoy the amenities. I would stay again."
Kelly 1-night trip
Posted 3 hours ago
Hideaway Inn Mt. Snow

Find out more about Chester

Chester B&B information

Number of reviews
2,493
Accommodation
66 B&B
Lowest Price
£59
Highest Price
£249

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.

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