Chester B&B: Find the Best Bed and Breakfast from CA $127

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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

Chester

John

CA $376 total

includes taxes & fees

Oct 15 - Oct 16

A room with a large window overlooking a lake and forested hills. There are two wooden chairs on a balcony.

2. Harvest Barn Inn

Bellows Falls

gail

CA $210 total

includes taxes & fees

Nov 2 - Nov 3

A calm lake reflecting a forest with autumn foliage.

3. Blue Gentian Lodge at Magic Mountain

Londonderry

Abigail

CA $214 total

includes taxes & fees

Nov 3 - Nov 4

A cozy room with a fireplace, green sofas, a pool table, and a lamp.

4. Bromley View Inn

Bondville

William

CA $127 total

includes taxes & fees

Nov 1 - Nov 2

A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.

5. Four Columns Inn

Newfane

CA $150 total

includes taxes & fees

Nov 2 - Nov 3

A wooden deck with a solar panel, surrounded by lush greenery and a hill in the background.

6. Windham Hill Inn

West Townshend

Nadine

CA $274 total

includes taxes & fees

Oct 20 - Oct 21

A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.

7. The Jackson

West Woodstock

Ava

CA $193 total

includes taxes & fees

Nov 3 - Nov 4

A large, multi-story building with a symmetrical facade, multiple windows, and a balcony with railings.

8. Echo Lake Inn

Plymouth

Amanda

CA $436 total

includes taxes & fees

Oct 13 - Oct 14

A large red barn and a white house with a porch, surrounded by trees and a well-maintained lawn.

9. The Inn at Manchester

Manchester Village Historic District

Reagan

CA $251 total

includes taxes & fees

Nov 2 - Nov 3

A bedroom with a bed, dresser, TV, and a chair.

10. Doveberry Inn

West Dover

Veronica

CA $188 total

includes taxes & fees

Nov 3 - Nov 4

A living room with a grey sectional sofa, a potted plant, and a radiator.

11. The Vesper

Woodstock

Keith

CA $259 total

includes taxes & fees

Nov 5 - Nov 6

A stone fire pit surrounded by rocks, with a tree in the background and a building with a red roof to the left.

12. Deerfield Valley Inn

West Dover

CA $152 total

includes taxes & fees

Nov 9 - Nov 10

A bedroom with a large bed, two bedside tables, a chair, and a mirror.

13. Colonel Williams Inn

Brattleboro

Amy

CA $227 total

includes taxes & fees

Nov 9 - Nov 10

A cozy living room with a fireplace, wicker chairs, and a coffee table with snacks.

14. Deer Brook Inn

Woodstock

Laurence

CA $364 total

includes taxes & fees

Nov 2 - Nov 3

A wooden table set with plates, cutlery, and a folded napkin.

15. The Carriage Barn Inn

Keene

Richard

CA $211 total

includes taxes & fees

Nov 8 - Nov 9

A garden with a large rock centerpiece, surrounded by various plants and a wooden structure in the background.

16. Big Bears Lodge

West Dover

Alfred

CA $270 total

includes taxes & fees

Oct 12 - Oct 13

A row of cabins with a snow-covered ground and trees in the background.

17. Sleep Woodstock - 2 Double Beds - Dog Friendly

Woodstock

CA $250 total

includes taxes & fees

Nov 9 - Nov 10

A two-story house with a covered patio area, a small outdoor seating area, and a gravel driveway.

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

Manchester

Ivy B.

CA $210 total

includes taxes & fees

Nov 2 - Nov 3

A modern fitness center with exercise equipment, mirrors, and a reception area.

19. Stay At Jimmy's

Woodstock

Jeanne

CA $468 total

includes taxes & fees

Oct 29 - Oct 30

A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.

20. Inn on Putney Road

Brattleboro

Karla

CA $418 total

includes taxes & fees

Nov 2 - Nov 3

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Top Chester Hotel Reviews

Latchis Hotel

10/10 Excellent

"Clean room, friendly staff. Great location for this hotel but limited parking."

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"The staff is amazing here at Jackson Gore Village. There were actually some issues with our stay and we reported to the front desk. The staff was really helpful and took care of the issue immediately. Katie, the manager, followed up the next day and further resolved the issue. The way they treat their customers makes me trust them in the future. We surely will come back."

Stone Hearth Inn and Eatery

8/10 Good

"Breakfast was very nice and staff very friendly… unfortunately it is not very accessible if you have walking difficulties … all the bedrooms are on the second floor and there are no elevators… l wish l had known this before l had booked the room …. we stayed 1 night even though we had reserved 2 nights because of the difficulty of the stairs… It was however nice if no handicaps"

The Manchester View

8/10 Good

"The lodge was in a picturesque location with lots of amenities. The rooms were clean apart from bugs in the window seals and in the main community areas. Lots of spider webs in lamp shades and around window areas. Just seemed to be overlooked for a long time. Unfortunately, we did not have a window screen on our room window in order to cool the room off due to the AC unit not functioning properly. We did find a fan which helped some. The breakfast was delicious and it was overall a comfortable place to stay and relax. I would definitely return for the views and location. Hopefully with the new staff in place, the lodge will improve in other areas needing attention."

Find out more about Chester

Chester B&B information

Number of reviews	2,141
Accommodation	65 B&B
Lowest Price	CA $127
Highest Price	CA $468

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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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester bed & breakfast

1. Stone Hearth Inn and Eatery

2. Harvest Barn Inn

3. Blue Gentian Lodge at Magic Mountain

4. Bromley View Inn

5. Four Columns Inn

6. Windham Hill Inn

7. The Jackson

8. Echo Lake Inn

9. The Inn at Manchester

10. Doveberry Inn

11. The Vesper

12. Deerfield Valley Inn

13. Colonel Williams Inn

14. Deer Brook Inn

15. The Carriage Barn Inn

16. Big Bears Lodge

17. Sleep Woodstock - 2 Double Beds - Dog Friendly

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

19. Stay At Jimmy's

20. Inn on Putney Road

Top Chester Hotel Reviews

Latchis Hotel

Hideaway Inn Mt. Snow

Jackson Gore Village, A Vail Resorts Property

Fullerton Inn

Colonial Motel

The Black Bear Lodge at Stratton Mountain Resort

Stone Hearth Inn and Eatery

The Manchester View

Woodstock Inn & Resort

Find out more about Chester

Chester B&B information

Frequently asked questions

Explore a world of travel with Expedia

Find a Bed and Breakfast in Chester from CA $127

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester bed & breakfast

1. Stone Hearth Inn and Eatery

2. Harvest Barn Inn

3. Blue Gentian Lodge at Magic Mountain

4. Bromley View Inn

5. Four Columns Inn

6. Windham Hill Inn

7. The Jackson

8. Echo Lake Inn

9. The Inn at Manchester

10. Doveberry Inn

11. The Vesper

12. Deerfield Valley Inn

13. Colonel Williams Inn

14. Deer Brook Inn

15. The Carriage Barn Inn

16. Big Bears Lodge

17. Sleep Woodstock - 2 Double Beds - Dog Friendly

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

19. Stay At Jimmy's

20. Inn on Putney Road

Top Chester Hotel Reviews

Latchis Hotel

Find out more about Chester

Chester B&B information

Frequently asked questions

Explore a world of travel with Expedia