Top B&B in Chester, VT

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

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B&B in Chester

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

$282

$307 total

includes taxes & fees

Oct 21 - Oct 22

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

A hotel hallway with wooden walls, a reception desk, and a sign indicating 'Employees Only'.

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

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.

2. Bromley View Inn

Bondville

$91

$100 total

includes taxes & fees

Nov 1 - Nov 2

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 two-story white house with a porch, a front yard, and a mailbox.

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.

3. Harvest Barn Inn

Bellows Falls

$152

$166 total

includes taxes & fees

Nov 4 - Nov 5

A calm lake reflecting a forest with autumn foliage.

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

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

A hot tub on a covered porch with a view of autumn foliage.

4. Blue Gentian Lodge at Magic Mountain

Londonderry

$149

$164 total

includes taxes & fees

Nov 3 - Nov 4

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

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

A narrow hallway leading to a bathroom with a toilet and shower curtain.

A panoramic view of a lake surrounded by forested hills.

5. Doveberry Inn

West Dover

$122

$134 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 spacious living area with a staircase, a red door, and a large window.

A long wooden table with red placemats and multiple wine glasses arranged for a tasting.

6. Four Columns Inn

Newfane

$107

$117 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 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.

A bedroom with a large window, a bed, a chair, and a lamp.

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

7. The Jackson

West Woodstock

$132

$145 total

includes taxes & fees

Nov 4 - Nov 5

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

A cozy room with a wooden floor, a rocking chair, a blue armchair, a bookshelf, and a globe on a table.

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.

8. The Carriage Barn Inn

Keene

$190

$206 total

includes taxes & fees

Oct 15 - Oct 16

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

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

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.

9. Windham Hill Inn

West Townshend

$186

$203 total

includes taxes & fees

Oct 20 - Oct 21

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

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

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

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

10. Colonel Williams Inn

Brattleboro

$158

$173 total

includes taxes & fees

Oct 13 - Oct 14

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.

11. The Vesper

Woodstock

$165

$182 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 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.

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

12. Deerfield Valley Inn

West Dover

$81

$117 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

A wooden-paneled room with a white sofa, a red pillow, a dark wooden cabinet, and a television mounted on the wall.

13. The Inn at Manchester

Manchester Village Historic District

$155

$196 total

includes taxes & fees

Nov 1 - Nov 2

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

A bar area with wooden bar counter, leather bar stools, and hanging stained glass lights.

A covered outdoor seating area with red chairs and tables, surrounded by white walls and red-framed windows.

14. Echo Lake Inn

Plymouth

$328

$358 total

includes taxes & fees

Oct 13 - Oct 14

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

A wooden deck with a hot tub, a wooden chair, and a broom leaning against the wall.

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

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

15. Deer Brook Inn

Woodstock

$233

$256 total

includes taxes & fees

Nov 1 - Nov 2

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 dining area with a round wooden table, white chairs, and a green wall.

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

16. Inn on Putney Road

Brattleboro

$267

$294 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

A modern interior with a black wall-mounted sign reading "HANGOUT".

17. Stay At Jimmy's

Woodstock

$299

$329 total

includes taxes & fees

Oct 29 - Oct 30

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

A wooden desk with a variety of books and pamphlets, a small tiger figurine, and a mirror reflecting the room.

18. The One Cat B&B

Brattleboro

$300

$330 total

includes taxes & fees

Oct 11 - Oct 12

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

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

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

19. Big Bears Lodge

West Dover

$173

$190 total

includes taxes & fees

Oct 9 - Oct 10

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

$301

$327 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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About the destination

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.