B&B in Chester

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Top 5 hotels in Chester at a glance

Stone Hearth Inn and Eatery — 3-star hotel in Chester. Guest rating: 9.2/10 — Wonderful.
Harvest Barn Inn — 3-star hotel in Bellows Falls. Guest rating: 9.8/10 — Exceptional.
Blue Gentian Lodge at Magic Mountain — 2.5-star hotel in Londonderry. Guest rating: 9.2/10 — Wonderful.
Bromley View Inn — 3.5-star hotel in Bondville. Guest rating: 9.0/10 — Wonderful.
Four Columns Inn — 4-star hotel in Newfane. Guest rating: 9.8/10 — Exceptional.

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 September 1, 2026.

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

A conference room with a long wooden table, multiple chairs, and a large window providing natural light.

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.

Stone Hearth Inn and Eatery

Chester

CNY1,404

CNY1,530 total

includes taxes & fees

Sep 7 - Sep 8

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

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.

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

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.

Harvest Barn Inn

Bellows Falls

CNY1,168

CNY1,273 total

includes taxes & fees

Sep 3 - Sep 4

A calm lake reflecting a forest with autumn foliage.

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

Blue Gentian Lodge at Magic Mountain

Londonderry

CNY1,001

CNY1,101 total

includes taxes & fees

Sep 3 - Sep 4

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

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

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.

Bromley View Inn

Bondville

CNY514

CNY565 total

includes taxes & fees

Sep 3 - Sep 4

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

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.

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

Four Columns Inn

Newfane

CNY1,052

CNY1,147 total

includes taxes & fees

Sep 3 - Sep 4

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

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

A breakfast table with a menu, a coffee pot, a mug, and a plate of pancakes and bacon.

Echo Lake Inn

Plymouth

CNY1,549

CNY1,688 total

includes taxes & fees

Sep 7 - Sep 8

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

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

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

The Jackson

West Woodstock

CNY1,049

CNY1,154 total

includes taxes & fees

Sep 8 - Sep 9

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

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.

The Carriage Barn Inn

Keene

CNY1,058

CNY1,148 total

includes taxes & fees

Sep 3 - Sep 4

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

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

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

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

Colonel Williams Inn

Brattleboro

CNY1,058

CNY1,164 total

includes taxes & fees

Sep 8 - Sep 9

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

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

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

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

Windham Hill Inn

West Townshend

CNY1,565

CNY1,706 total

includes taxes & fees

Sep 22 - Sep 23

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.

The Inn at Manchester

Manchester Village Historic District

CNY937

CNY1,186 total

includes taxes & fees

Sep 9 - Sep 10

A two-story house with a red roof and grey siding, a front porch, and a stack of firewood.

Doveberry Inn

West Dover

CNY1,016

CNY1,118 total

includes taxes & fees

Sep 3 - Sep 4

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

A neatly made bed with a white duvet, two bedside tables with lamps, and a decorative plate on the wall.

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

The Vesper

Woodstock

CNY1,176

CNY1,293 total

includes taxes & fees

Sep 7 - Sep 8

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 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.

Deer Brook Inn

Woodstock

CNY1,563

CNY1,720 total

includes taxes & fees

Sep 6 - Sep 7

A porch with wicker chairs, potted plants, and a number '43' sign.

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

The One Cat B&B

Brattleboro

CNY2,016

CNY2,217 total

includes taxes & fees

Sep 8 - Sep 9

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

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

A fireplace with a fire burning inside, a metal screen, and a handle on the right side.

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

Deerfield Valley Inn

West Dover

CNY591

CNY835 total

includes taxes & fees

Sep 24 - Sep 25

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

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.

Big Bears Lodge

West Dover

CNY1,159

CNY1,275 total

includes taxes & fees

Sep 3 - Sep 4

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

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

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

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

Inn on Putney Road

Brattleboro

CNY1,980

CNY2,179 total

includes taxes & fees

Sep 3 - Sep 4

A house with a red roof, a porch with white railings, and a blue door.

A wooden dining table with a woven tray, a vase with dried flowers, a small potted plant, and two candles.

A cozy living room with a Christmas tree, a sofa, a coffee table, and a fireplace.

A living room with a sofa, armchair, coffee table, bookshelf, and a ceiling fan.

Woodbridge Inn

Woodstock

CNY3,326

CNY3,659 total

includes taxes & fees

Sep 7 - Sep 8

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

Stay At Jimmy's

Woodstock

CNY2,345

CNY2,580 total

includes taxes & fees

Sep 10 - Sep 11

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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 DaVallia Art & Accents and Bonnie's Bundles Dolls.

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Top landmarks in Chester

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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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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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 the local cuisine and its coffee shops. 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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