20 Best B&B in Chester, VT - Bed and Breakfast from AED 168

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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

AED 769 total

includes taxes & fees

16 Nov - 17 Nov

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

John

AED 638 total

includes taxes & fees

28 Nov - 29 Nov

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

3. Bromley View Inn

Bondville

BARBARA

AED 330 total

includes taxes & fees

22 Nov - 23 Nov

A snow-covered cabin with a large window, surrounded by trees and a mountain in the background.

4. Blue Gentian Lodge at Magic Mountain

Londonderry

Abigail

AED 602 total

includes taxes & fees

9 Nov - 10 Nov

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

5. Four Columns Inn

Newfane

Raymond

AED 602 total

includes taxes & fees

10 Nov - 11 Nov

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

6. The Jackson

West Woodstock

Ava

AED 498 total

includes taxes & fees

11 Nov - 12 Nov

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

7. Echo Lake Inn

Plymouth

richard

AED 1,287 total

includes taxes & fees

25 Nov - 26 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

Ted

AED 287 total

includes taxes & fees

22 Nov - 23 Nov

A two-story building with a blue exterior, a wooden front porch, and a sign indicating a vacancy.

9. Doveberry Inn

West Dover

Veronica

AED 502 total

includes taxes & fees

16 Nov - 17 Nov

A large, snow-covered house with multiple windows and a well-lit porch.

10. The Inn at Manchester

Manchester Village Historic District

Zhihao

AED 648 total

includes taxes & fees

9 Nov - 10 Nov

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

11. Deer Brook Inn

Woodstock

Laurence

AED 931 total

includes taxes & fees

9 Nov - 10 Nov

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

12. The Vesper

Woodstock

Rhea

AED 666 total

includes taxes & fees

10 Nov - 11 Nov

A room with two single beds, a desk, and a radiator.

13. Colonel Williams Inn

Brattleboro

Amy

AED 707 total

includes taxes & fees

22 Nov - 23 Nov

A dining area with wooden tables and chairs, large windows with a view of trees, and a bench along the wall.

14. The Carriage Barn Inn

Keene

Richard

AED 435 total

includes taxes & fees

16 Nov - 17 Nov

A two-story house with a snow-covered roof and yard, featuring multiple lit windows and a visible chimney.

15. The Inn at Ormsby Hill

Manchester Center

Victoria

AED 925 total

includes taxes & fees

10 Nov - 11 Nov

A small room with a table and two chairs, a window with curtains, and a lamp on the table.

16. Alpine 5, cozy Vermont retreat

Manchester

Shuo P.

AED 531 total

includes taxes & fees

16 Nov - 17 Nov

A sign for Big Bear's Lodge advertising a heated pool, hot tub, and free WiFi.

17. Big Bears Lodge

West Dover

Alfred

AED 697 total

includes taxes & fees

29 Nov - 30 Nov

A modern living room with a sofa, chairs, a coffee table, a fireplace, and a kitchen area in the background.

18. Sleep Woodstock - 2 Double Beds - Dog Friendly

Woodstock

AED 594 total

includes taxes & fees

30 Nov - 1 Dec

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

19. Inn on Putney Road

Brattleboro

Karla

AED 1,078 total

includes taxes & fees

10 Nov - 11 Nov

A large, two-story house with a snow-covered driveway and surrounding trees.

20. Chesterfield Inn

West Chesterfield

Wayne

AED 1,200 total

includes taxes & fees

15 Nov - 16 Nov

View all properties

Learn more about Chester

Nestled in a relaxing small-town setting, Chester invites visitors to explore DaVallia Art & Accents and browse handcrafted treasures at Bonnie's Bundles Dolls. Outdoor enthusiasts can enjoy nearby Stoughton Pond Recreation Area or take a scenic drive to Lowell Lake State Park and the charming Vermont Country Store.

See all hotels in Chester

A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Top reviews in Chester

Stone Hearth Inn and Eatery

Chester

10/10 Excellent

William

Harvest Barn Inn

Bellows Falls

10/10 Excellent

Virginia

The Inn at Manchester

Manchester Village Historic District

10/10 Excellent

Mary

Four Columns Inn

Newfane

10/10 Excellent

Nettie

Blue Gentian Lodge at Magic Mountain

Londonderry

10/10 Excellent

Anonymous traveler

Colonel Williams Inn

Brattleboro

10/10 Excellent

Beautiful Vermont Inn with exceptional breakfast: changes everyday - we had frittata, fresh fruit, steel cut oats fried with maple syrup and pecans and always muffins or other baked goods. Our hosts were friendly, accommodating and know the area well. We had room 3- spacious and comfortable. When it snows there is a 5 mile snowshoe,cross country trail on the property for guests only. We were there to attend a show at the Vermont Jazz Center in Brattleboro-about 20 min away. Also hiked...

Ann

The Carriage Barn Inn

Keene

10/10 Excellent

Richard

The Inn at Ormsby Hill

Manchester Center

10/10 Excellent

The Inn at Ormsby Hill is a magnificent B&B in historic Manchester Vermont. We were in Vermont for a ski week vacation. We ended our trip staying at this Inn and skiing at Stratton Ski Area. When we arrived, the Innkeeper Maryanne greeted us then suggested we move our room to one more centrally located. Our room was beautiful with a 4 post king bed, gas fireplace and plush bathrobes. The daily breakfast was superb! The dining area was full of antiques, many from the Pullman Corporation. Edward...

Anonymous traveler

Echo Lake Inn

Plymouth

10/10 Excellent

Deb

Inn on Putney Road

Brattleboro

10/10 Excellent

Victoria

Chesterfield Inn

West Chesterfield

10/10 Excellent

Our stay at the Chesterfield Inn was absolutely wonderful. The inn is sweet, charming, and full of character. We slept so good and our room was so peaceful. We were treated to a beautiful sunset, enjoyed a delicious breakfast next morning, and appreciated the warm hospitality throughout our stay. The staff was exceptionally kind, welcoming, and helpful, making us feel right at home. We would definitely stay here again and highly recommend it to anyone looking for a relaxing New England getaway.

Beverly

Doveberry Inn

West Dover

10/10 Excellent

This was a unique experience for me. It was like having a nice room in a log cabin. It was very quiet and peaceful right off the winding country road sitting in front of a forest with a beautiful outlook from the dining area. There was good self serve beverage options available when I arrived in the late evening and breakfast the next morning had enough quality items for a gluten free person like myself. No bread or baked goods for me but nice yogurt, fresh fruit and coffee. The owner Nick...

Hilda

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.

Search B&B 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. Harvest Barn Inn

3. Bromley View Inn

4. Blue Gentian Lodge at Magic Mountain

5. Four Columns Inn

6. The Jackson

7. Echo Lake Inn

8. Deerfield Valley Inn

9. Doveberry Inn

10. The Inn at Manchester

11. Deer Brook Inn

12. The Vesper

13. Colonel Williams Inn

14. The Carriage Barn Inn

15. The Inn at Ormsby Hill

16. Alpine 5, cozy Vermont retreat

17. Big Bears Lodge

18. Sleep Woodstock - 2 Double Beds - Dog Friendly

19. Inn on Putney Road

20. Chesterfield Inn

Learn more about Chester

Top reviews in Chester

Stone Hearth Inn and Eatery

10/10 Excellent

Frequently Asked Questions

Searching for B&Bs in Chester?

Are you thinking about B&Bs over traditional hotel rooms?

What are the top B&Bs in Chester?

How many Bed & Breakfasts should I expect to find in Chester?

What's the best time of year to stay at a B&B in Chester?

What is there to do in Chester?

How can I get to and around Chester?