Chester B&B: Best Bed and Breakfast 2026

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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

includes taxes & fees

13 Nov - 14 Nov

A calm lake reflecting a forest with autumn foliage.

2. Blue Gentian Lodge at Magic Mountain

Londonderry

Abigail

includes taxes & fees

3 Nov - 4 Nov

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

3. Harvest Barn Inn

Bellows Falls

gail

includes taxes & fees

1 Nov - 2 Nov

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

4. Bromley View Inn

Bondville

BARBARA

includes taxes & fees

1 Nov - 2 Nov

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

5. Four Columns Inn

Newfane

Raymond

includes taxes & fees

2 Nov - 3 Nov

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

6. Windham Hill Inn

West Townshend

Nadine

includes taxes & fees

26 Oct - 27 Oct

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

7. The Jackson

West Woodstock

Ava

includes taxes & fees

3 Nov - 4 Nov

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

West Dover

Patrick

includes taxes & fees

1 Nov - 2 Nov

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

includes taxes & fees

1 Nov - 2 Nov

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

10. Doveberry Inn

West Dover

Veronica

includes taxes & fees

25 Oct - 26 Oct

A four-poster bed with a round mirror above it, two bedside tables with lamps, and a patterned rug on the floor.

11. The Vesper

Woodstock

Keith

includes taxes & fees

9 Nov - 10 Nov

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

12. Deer Brook Inn

Woodstock

Laurence

includes taxes & fees

1 Nov - 2 Nov

A large white building with a stone wall and a lawn covered in fallen leaves.

13. Colonel Williams Inn

Brattleboro

Amy

includes taxes & fees

20 Oct - 21 Oct

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

14. The Carriage Barn Inn

Keene

Richard

includes taxes & fees

15 Oct - 16 Oct

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

15. Big Bears Lodge

West Dover

Alfred

includes taxes & fees

28 Oct - 29 Oct

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

16. Sleep Woodstock - 2 Double Beds - Dog Friendly

Woodstock

includes taxes & fees

9 Nov - 10 Nov

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

Manchester

Ivy B.

includes taxes & fees

2 Nov - 3 Nov

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

18. Inn on Putney Road

Brattleboro

Karla

includes taxes & fees

10 Nov - 11 Nov

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

Manchester Center

Victoria

includes taxes & fees

10 Nov - 11 Nov

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

20. Stay At Jimmy's

Woodstock

Jeanne

includes taxes & fees

29 Oct - 30 Oct

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Top Chester Hotel Reviews

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"Beautiful location and convenient location for Golf trip to Vermont. Only one working outlet in the room was an inconvenience."

Grand Summit Resort, A Vail Resorts Property

8/10 Good

"The accommodations were very good but was disappointed that they made us pay $20 to park for the day we were leaving because we asked to stay in the lobby for an extra hour until we could pick up our grandson up at a neighboring ski camp. Especially since the parking lot was not full & we were there for four nights."

Aspen At Manchester

10/10 Excellent

"Great location, simple room--minimalist but nice with microwave, fridge. Was a great place to set up headquarters for our trip to Vermont. Beautiful view behind the motel with firepits. It is a self-serve kind of property, which suited us well. We stayed 4 days and they didn't come to clean throughout. But we could go to the office and pick up anything we needed: extra toiletries, towels, etc. We enjoyed staying at the Aspen."

Pointe at Castle Hill Resort

10/10 Excellent

"My sister and I needed a very last minute place to stay after our VRBO rental was not what we thought. The ladies at the front desk were really nice and very help. The beds and pillows were very comfortable and the room was very clean. The only issue is the area, it’s a bit of a drive if you want to shop however, one minute up the road is Murdoch’s restaurant and they had delicious food. We ate there twice. Just make sure to make a reservation. All in all it was a nice stay and we definitely suggest staying there."

Find out more about Chester

Chester B&B information

Number of reviews	2,493
Accommodation	66 B&B
Lowest Price	€70
Highest Price	€294

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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Check prices for these dates

Our top choices for Chester bed & breakfast

1. Stone Hearth Inn and Eatery

2. Blue Gentian Lodge at Magic Mountain

3. Harvest Barn Inn

4. Bromley View Inn

5. Four Columns Inn

6. Windham Hill Inn

7. The Jackson

8. Deerfield Valley Inn

9. The Inn at Manchester

10. Doveberry Inn

11. The Vesper

12. Deer Brook Inn

13. Colonel Williams Inn

14. The Carriage Barn Inn

15. Big Bears Lodge

16. Sleep Woodstock - 2 Double Beds - Dog Friendly

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

18. Inn on Putney Road

19. The Inn at Ormsby Hill

20. Stay At Jimmy's

Top Chester Hotel Reviews

Jackson Gore Village, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

Aspen At Manchester

Latchis Hotel

Pointe at Castle Hill Resort

The Manchester View

Fullerton Inn

The Equinox Golf Resort And Spa

Hampton Inn and Suites Manchester

Find out more about Chester

Chester B&B information

Frequently asked questions

Search Bed and Breakfast in Chester

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. Blue Gentian Lodge at Magic Mountain

3. Harvest Barn Inn

4. Bromley View Inn

5. Four Columns Inn

6. Windham Hill Inn

7. The Jackson

8. Deerfield Valley Inn

9. The Inn at Manchester

10. Doveberry Inn

11. The Vesper

12. Deer Brook Inn

13. Colonel Williams Inn

14. The Carriage Barn Inn

15. Big Bears Lodge

16. Sleep Woodstock - 2 Double Beds - Dog Friendly

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

18. Inn on Putney Road

19. The Inn at Ormsby Hill

20. Stay At Jimmy's

Top Chester Hotel Reviews

Jackson Gore Village, A Vail Resorts Property

Find out more about Chester

Chester B&B information

Frequently asked questions