B&B in Chester

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B&B in Chester

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Chester on Hotels.com. These Chester B&B consistently deliver on quality, location and traveler experience. Last updated on October 17, 2026.

A red barn with a white door and shutters, surrounded by a garden with various plants and flowers.

A bedroom with a bed, a fireplace, a window, a dresser, and a clock on the wall.

A white house with a porch, wooden chairs, and an American flag.

A living room with two sofas, a fireplace, and a wooden floor.

1. Stone Hearth Inn and Eatery

Chester

CNY1,397

CNY1,522 total

includes taxes & fees

Nov 16 - Nov 17

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

A dining area with a table and chairs, a window with a view of trees, a potted plant, and a door with a view of a mountain.

A neatly made bed with a white comforter and pillows, a wooden nightstand with a lamp, and a wall hanging above the bed.

A room with a wooden table, two chairs, a vase with flowers, a hanging plant, a framed picture on the wall, and a patterned rug.

2. Harvest Barn Inn

Bellows Falls

CNY1,018

CNY1,110 total

includes taxes & fees

Nov 1 - Nov 2

A calm lake reflecting a forest with autumn foliage.

A house with a balcony and a garden with red flowers.

A modern house with a pool, surrounded by lush greenery and mountains in the background.

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

3. Blue Gentian Lodge at Magic Mountain

Londonderry

CNY996

CNY1,096 total

includes taxes & fees

Nov 3 - Nov 4

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

A deck with white railings overlooking a forested area and a mountain in the distance.

A wooden interior with a dining table set for four, a wooden cabinet with glass doors, and a kitchen area with a refrigerator and cabinets.

A bedroom with a wooden floor, a bed with a white bedspread, a nightstand with a lamp, a dresser, and a television on the dresser.

4. Bromley View Inn

Bondville

CNY504

CNY555 total

includes taxes & fees

Nov 1 - Nov 2

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

A panoramic view of a lake surrounded by forested hills.

A bathroom with a double sink, a large mirror, and a bed with a blue patterned bedspread.

A bunk bed with a blue patterned bedspread and a white pillow.

5. Doveberry Inn

West Dover

CNY812

CNY894 total

includes taxes & fees

Oct 25 - Oct 26

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

A serene pond with a statue in the center, surrounded by lush greenery and trees.

A living room with leather sofas, a round ottoman, a fireplace, and a bookshelf.

A spacious living area with a staircase, a red door, and a large window.

6. Four Columns Inn

Newfane

CNY715

CNY780 total

includes taxes & fees

Nov 2 - Nov 3

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

A well-maintained lawn with a central garden area, a brick building, and a view of a forested hill.

A two-story house with a porch, American flags, and a well-maintained garden.

A cozy room with a wooden bench, a chair, and a sofa. There are large windows with wooden frames and a chandelier hanging from the ceiling.

7. The Jackson

West Woodstock

CNY824

CNY906 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.

A snow-covered landscape with a tree illuminated by string lights, a red building, and a street in the background.

A living room with a stone wall, a television, and a fireplace.

A two-story house with a dark brown exterior, a dark blue front door, and a small porch area.

8. Deerfield Valley Inn

West Dover

CNY308

CNY522 total

includes taxes & fees

Nov 1 - Nov 2

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

A two-story building with a porch, a sign indicating guest rooms, and an American flag.

A bench in front of an apple tree with ripe apples.

A corner room with wooden flooring, a wooden table, and four chairs. Large windows with curtains are visible, offering a view of a green landscape and a red deck outside.

9. The Carriage Barn Inn

Keene

CNY1,129

CNY1,225 total

includes taxes & fees

Oct 18 - Oct 19

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

A kitchen with wooden cabinets, a built-in stove, a microwave, and a sink.

A stone pathway leading to a porch with a wooden railing, surrounded by lush greenery and a lattice fence.

A room with a stone fireplace, large windows with curtains, a patterned rug, and a plush chair.

10. Windham Hill Inn

West Townshend

CNY1,181

CNY1,287 total

includes taxes & fees

Oct 28 - Oct 29

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

A swimming pool with lounge chairs, a red building with a tower, and lush greenery.

A bar area with wooden flooring, a leather sofa, and a bar counter with a variety of liquor bottles.

A cozy living room with a fireplace, bookshelves, and comfortable seating.

11. The Inn at Manchester

Manchester Village Historic District

CNY933

CNY1,180 total

includes taxes & fees

Nov 12 - Nov 13

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

A large white house with a dark roof, surrounded by snow-covered ground and trees.

A long banquet table set up in a rustic barn with string lights and paper lanterns.

A pathway leading to a gazebo in a park with a pond and trees.

12. Colonel Williams Inn

Brattleboro

CNY1,053

CNY1,158 total

includes taxes & fees

Oct 20 - Oct 21

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

A dining area with a white table, two white chairs, a small vase with flowers, and a framed artwork on the wall.

A cozy living room with a high ceiling, a wooden floor, a sofa, a chair, and a small table.

13. The Vesper

Woodstock

CNY1,103

CNY1,214 total

includes taxes & fees

Nov 15 - Nov 16

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

A living room with a beige sofa, a wooden coffee table, and a fireplace. There are framed pictures on the walls and a lamp on a side table.

A two-story house with a covered porch and a well-maintained garden.

A room with a wooden desk, a lamp, and two leather sofas with patterned cushions.

14. Deer Brook Inn

Woodstock

CNY1,556

CNY1,711 total

includes taxes & fees

Nov 15 - Nov 16

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

A covered porch with wicker furniture, a white railing, and a view of greenery.

A bathroom with a large bathtub, a mirror with a gold frame, and a wooden chair with a towel.

A large, white two-story house with a stone wall and yellow flowers in the foreground.

15. The Inn at Ormsby Hill

Manchester Center

CNY1,732

CNY1,905 total

includes taxes & fees

Nov 8 - Nov 9

A blue house with a porch, a sign reading "The One Cat", and a garden with various plants and flowers.

A bedroom with a bed, a headboard with a birdcage design, a nightstand with a lamp, and a window with blue curtains.

A cozy living room with a television, books, and a comfortable couch.

A garden with a sign reading "The One Cat" and various plants and flowers.

16. The One Cat B&B

Brattleboro

CNY2,006

CNY2,207 total

includes taxes & fees

Oct 20 - Oct 21

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

A cozy living room with a piano, leather sofa, armchair, and a globe on a coffee table.

A room with a chessboard, leather chairs, a large vase, and a bookshelf.

A living room with a fireplace, a pool table, and comfortable seating.

17. Inn on Putney Road

Brattleboro

CNY1,785

CNY1,963 total

includes taxes & fees

Nov 3 - Nov 4

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

A room with a 'RELAX' sign, a black leather sofa, and a patterned floor.

A two-story building with a porch, a sign reading "STAY AT JIMMY'S", and a pathway leading to it.

A modern kitchen with white cabinets, a built-in oven, and a microwave.

18. Stay At Jimmy's

Woodstock

CNY1,999

CNY2,199 total

includes taxes & fees

Oct 29 - Oct 30

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

A spacious dining area with multiple wooden tables and chairs, large windows with curtains, and a wooden ceiling.

A living room with a stone fireplace, a television, a brown sofa, and a wooden coffee table.

A house with a porch, a wooden staircase, and a welcome sign.

19. Big Bears Lodge

West Dover

CNY1,153

CNY1,269 total

includes taxes & fees

Oct 28 - Oct 29

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

A bedroom with a large bed, a blue armchair, a wooden desk, and a view through a glass door.

A cozy living room with a fireplace, leather chairs, a sofa, and a table with wine glasses.

A cozy room with a brick fireplace, floral wallpaper, and comfortable seating.

20. Chesterfield Inn

West Chesterfield

CNY2,014

CNY2,185 total

includes taxes & fees

Oct 18 - Oct 19

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Top neighborhoods in Chester

Chester Depot

A forest with autumn foliage in various colors.

Chester Depot

The Chester Depot neighborhood has lots to see including Bonnie's Bundles Dolls and DaVallia Art & Accents.

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Top landmarks in Chester

Bonnie's Bundles Dolls

7.6/10 (4 reviews)

Chester Depot is home to Bonnie's Bundles Dolls, so why not stop by during your stay in Chester. If you have fun at Bonnie's Bundles Dolls, you'll love DaVallia Art & Accents, located nearby.

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DaVallia Art & Accents

10.0/10 (2 reviews)

Chester Depot is home to DaVallia Art & Accents, so why not stop by during your stay in Chester. If you have fun at DaVallia Art & Accents, you'll love Bonnie's Bundles Dolls, located nearby.

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Learn more about Chester

Notable for its skiing, Chester features attractions such as DaVallia Art & Accents and Bonnie's Bundles Dolls. Visitors speak highly of this relaxing city's coffeehouses and small-town setting.

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

Find out more about Chester

Chester is a relaxing city where you can spend time checking out its coffee shops and the local cuisine. If you're visiting during colder months, enjoy activities such as skiing during your stay. Why not take time to see places like DaVallia Art & Accents and Bonnie's Bundles Dolls? In the surrounding area, you won't want to miss out on seeing Whitney Hill and Springfield Art and Historical Society Museum.

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