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Check prices for these dates

Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct
In one month
6 Nov - 8 Nov
In two months
4 Dec - 6 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 AU$405
includes taxes & fees
13 Oct - 14 Oct
Stone Hearth Inn and Eatery
A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

2. Harvest Barn Inn

Harvest Barn Inn
3.0 star property
Bellows Falls
9.8 out of 10, Exceptional, (291 reviews)
"The breakfasts were amazing and the hosts were super kind and helpful!"
United States
gail
The price is AU$209
includes taxes & fees
1 Nov - 2 Nov
Harvest Barn Inn
A calm lake reflecting a forest with autumn foliage.

3. 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 AU$235
includes taxes & fees
3 Nov - 4 Nov
Blue Gentian Lodge at Magic Mountain
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, (492 reviews)
"Pleasant stay - excellent breakfast!"
Canada
William
The price is AU$127
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, (60 reviews)
"Lovely grounds, great location, wonderful restaurant. Staff was very pleasant and helpful. Just booke another stay."
United States
Raymond
The price is AU$150
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, (46 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 AU$276
includes taxes & fees
22 Oct - 23 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, (330 reviews)
"Amazing stay and great restaurant!"
United States
Ava
The price is AU$194
includes taxes & fees
3 Nov - 4 Nov
The Jackson
A large, multi-story building with a symmetrical facade, multiple windows, and a balcony with railings.

8. Echo Lake Inn

Echo Lake Inn
2.5 star property
Plymouth
8.8 out of 10, Excellent, (106 reviews)
"Beautiful property! The charm and character of the place were amazing. Staff was friendly and very helpful. Rooms were quaint and well appointed, clean with comfy beds!"
United States
Amanda
The price is AU$463
includes taxes & fees
13 Oct - 14 Oct
Echo Lake Inn
A bedroom with a bed, dresser, TV, and a chair.

9. 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 AU$189
includes taxes & fees
28 Oct - 29 Oct
Doveberry Inn
A large red barn and a white house with a porch, surrounded by trees and a well-maintained lawn.

10. The Inn at Manchester

The Inn at Manchester
3.5 star property
Manchester Village Historic District
10.0 out of 10, Exceptional, (388 reviews)
"Super clean, great location and really reasonable per night."
United States
Reagan
The price is AU$253
includes taxes & fees
1 Nov - 2 Nov
The Inn at Manchester
A stone fire pit surrounded by rocks, with a tree in the background and a building with a red roof to the left.

11. 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 AU$153
includes taxes & fees
1 Nov - 2 Nov
Deerfield Valley 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, (80 reviews)
"Room great breakfast fantastic Location a 10"
United States
Keith
The price is AU$260
includes taxes & fees
10 Nov - 11 Nov
The Vesper
A cozy living room with a fireplace, wicker chairs, and a coffee table with snacks.

13. 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 AU$366
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.

14. 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 AU$228
includes taxes & fees
20 Oct - 21 Oct
Colonel Williams Inn
A wooden table set with plates, cutlery, and a folded napkin.

15. 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 AU$231
includes taxes & fees
15 Oct - 16 Oct
The Carriage Barn Inn
A garden with a large rock centerpiece, surrounded by various plants and a wooden structure in the background.

16. Big Bears Lodge

Big Bears Lodge
3.0 star property
West Dover
9.0 out of 10, Wonderful, (219 reviews)
"Welcoming host with great customer service"
United States
Alfred
The price is AU$272
includes taxes & fees
12 Oct - 13 Oct
Big Bears Lodge
A row of cabins with a snow-covered ground and trees in the background.

17. Sleep Woodstock - 2 Double Beds - Dog Friendly

Sleep Woodstock - 2 Double Beds - Dog Friendly
Woodstock
The price is AU$254
includes taxes & fees
9 Nov - 10 Nov
Sleep Woodstock - 2 Double Beds - Dog Friendly
A modern fitness center with exercise equipment, mirrors, and a reception area.

18. 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 AU$471
includes taxes & fees
29 Oct - 30 Oct
Stay At Jimmy's
A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.

19. 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 AU$420
includes taxes & fees
1 Nov - 2 Nov
Inn on Putney Road
A cozy room with a bed, a sofa, a wooden table, and a coffee machine.

20. 3, cozy pet friendly Vermont retreat - two doubles

3, cozy pet friendly Vermont retreat - two doubles
Manchester
8.0 out of 10, Very good, (2 reviews)
"Great place! Loved the shared full kitchen! Loved all the seating outdoors to enjoy the mountains!!! Was centrally located to enjoy surrounding areas. Host was very responsive to questions."
United States
Cheryl C.
The price is AU$214
includes taxes & fees
2 Nov - 3 Nov
3, cozy pet friendly Vermont retreat - two doubles
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 Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"Beautiful place for getaway!!!😊"
Esther 2-night trip
Posted 12 hours ago
The Black Bear Lodge at Stratton Mountain Resort

Find out more about Chester

Chester B&B information

Number of reviews
2,125
Accommodation
66 B&B
Lowest Price
AU$127
Highest Price
AU$471

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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