𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Chester (2026)

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Hot tub

Pool

Condo

Spa

Cottage

Family friendly

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Our top choices for Chester hotels

A well-maintained garden with a variety of plants and flowers, a wooden pergola, and a gravel path.

A two-story building with a central entrance, a balcony with railings, and a sign indicating it is a lodging and fine dining establishment.

A variety of dishes including a steak, muffins, and a dessert with fruit.

A cozy living room with a stone fireplace, a leather sofa set, a wooden coffee table, and a patterned rug.

1. Fullerton Inn

Chester Depot

kris

S$208

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

2. Stone Hearth Inn and Eatery

Chester

John

S$369

includes taxes & fees

8 Oct - 9 Oct

A hotel with a covered entrance, stone facade, and a sign indicating it is part of the Best Western chain.

A spacious, well-lit kitchen area with modern appliances, a central island with bar stools, and a chandelier.

An indoor swimming pool with clear water, lounge chairs, and a stone fireplace.

A hotel room with a bed, a sofa, a coffee table, a desk, and a TV.

3. Best Western Springfield Hotel

Springfield

Gerry

S$214

includes taxes & fees

1 Nov - 2 Nov

A spa named Castle Hill Spa with a well-maintained lawn and a pathway leading to the entrance.

A kitchen with wooden cabinets, a white microwave, a stove, and a refrigerator.

A spacious lobby with a fireplace, leather seating, and a chandelier.

An indoor swimming pool with four chairs and a hot tub.

4. Pointe at Castle Hill Resort

Cavendish

Cristian

S$215

includes taxes & fees

21 Oct - 22 Oct

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

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.

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.

5. Harvest Barn Inn

Bellows Falls

gail

S$197

includes taxes & fees

1 Nov - 2 Nov

A bedroom with a fireplace, two beds, a chair, and a nightstand.

A living room with a fireplace, a sofa, a coffee table, and a chair.

A large, two-story house with a central entrance, surrounded by trees and a mountain backdrop.

A living room with a fireplace, a sofa, a coffee table, and a view through a sliding glass door.

6. The Manchester View

Manchester Center

Gregory

S$119

includes taxes & fees

5 Nov - 6 Nov

A restaurant with wooden tables and chairs, a central table with a sign reading "The Red Slate Restaurant", and large windows with views of the outside.

A bar area with a sign reading "MAGIC" and "featured Vermont beers".

A Christmas tree decorated with lights, ornaments, and a bow.

A hotel room with a large bathtub, a bed with a colorful quilt, two bedside lamps, and a framed picture on the wall.

7. The Upper Pass Lodge at Magic Mountain

Londonderry

Terry

S$159

includes taxes & fees

1 Nov - 2 Nov

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

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

8. Bromley View Inn

Bondville

William

S$115

includes taxes & fees

1 Nov - 2 Nov

A rustic dining area with wooden beams, tables, chairs, and a fireplace.

A living room with a sofa, ottoman, armchair, and a television on a stand.

An outdoor event space with tables set for dining, surrounded by a covered area with a transparent roof.

A bedroom with a large bed, a bedside table, a lamp, and a view of the outdoors through a sliding door.

9. The Inn at Weathersfield

Perkinsville

Rula

S$347

includes taxes & fees

3 Nov - 4 Nov

A hotel room with two beds, a wooden headboard, bedside lamps, and a window with curtains.

A picnic table with benches in a grassy area in front of a motel with multiple cars parked in the driveway.

A reception desk with a check-in counter, a framed picture above it, and a potted plant to the right.

A hotel room with a desk, chair, television, refrigerator, and a dresser.

10. Claremont Motor Lodge

Claremont

Jerri

S$153

includes taxes & fees

18 Oct - 19 Oct

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

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

11. Blue Gentian Lodge at Magic Mountain

Londonderry

Abigail

S$209

includes taxes & fees

5 Nov - 6 Nov

A modern kitchen with a central island, stainless steel appliances, and a dining area with chairs.

A red car parked at a charging station in front of a building with a 'OPEN' sign.

A hotel room with two beds, a desk, and a chair. The room has a wooden floor and red walls with framed pictures.

A modern kitchen with a wooden dining table, stainless steel appliances, and a view of the outdoors through the window.

12. Sleep Woodstock Motel

Woodstock

michelle

S$177

includes taxes & fees

27 Oct - 28 Oct

A hotel with multiple buildings, a covered outdoor area, and a snowy landscape.

A hot tub with a tiled interior and a window in the background.

A balcony with a stone wall and wooden railing overlooking a grassy area with a building in the background.

A hotel with a swimming pool area, including two hot tubs and lounge chairs.

13. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area

Daniel

S$280

includes taxes & fees

26 Oct - 27 Oct

A bay window seating area with a round table, a potted plant, and a garland with pine cones and lights.

A room with a red sofa, armchairs, a coffee table, and a fireplace. There is a window with a view of trees and a chandelier.

A restaurant with a stone wall bar area, wooden tables, and chairs.

A living room with a fireplace, two armchairs, a TV mounted above the fireplace, and a desk with a mirror and lamp.

14. The Hartness House

Springfield

Elizabeth

S$279

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

15. Four Columns Inn

Newfane

Raymond

S$139

includes taxes & fees

3 Nov - 4 Nov

A cozy living room with a fireplace, leather furniture, and a coffee table with a puzzle.

A cozy room with a large bed, a fireplace, and a brick wall.

A wooden interior with a pool, benches, and a clock.

A metal bucket with a spoon, two wine glasses, and a checkered cloth on a brick ledge by a pool.

16. The Common Man Inn & Restaurant

Claremont

Bruce

S$180

includes taxes & fees

1 Nov - 2 Nov

A sign for The Putney Inn, a restaurant and motel, with a friendly welcome message and floral decorations.

A two-story white house with a front porch and a garage, surrounded by lush greenery.

A hotel room with two beds, a desk, and a TV.

A grassy field with a playground and trees in the background.

17. The Putney Inn

Putney

Elizabeth G

S$118

includes taxes & fees

25 Oct - 26 Oct

A multi-story hotel with a central courtyard and a reflective water feature.

A bar area with stools, a counter, and a large window offering a view of a snowy landscape.

A group of people gathered around a fire pit in a snowy outdoor setting with a large building in the background.

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

18. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

Shannon

S$242

includes taxes & fees

27 Oct - 28 Oct

A cozy room with a sofa, armchair, and round table, decorated with leaf-patterned artwork and a lamp.

A bar area with wooden ceiling, shelves with bottles, and a bar counter.

A hotel room with a bed, a chair, a table, and a view of mountains through a large window.

A multi-story hotel with balconies, a ski slope in the background, and a clear blue sky.

19. Sun Lodge near Manchester VT, Ascend Collection Hotel

Bromley Mountain

Glen

S$161

includes taxes & fees

5 Nov - 6 Nov

A large stone building with a steep roof, surrounded by dense forest and hills.

A hotel room with a bed, a nightstand, a lamp, a door, and a view into another room with a couch and a window.

A spacious living room with a fireplace, red sofas, a wooden coffee table, and a television.

A traditional bedroom with a four-poster bed, two armchairs, a wooden wardrobe, and a mirror.

20. Castle Hill Resort And Spa

Cavendish

Brandon

S$307

includes taxes & fees

19 Oct - 20 Oct

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Where to stay in Chester

Find the best Chester areas for the activities you enjoy most.

Chester Depot

A forest with autumn foliage in various colors.

Chester Depot

If you're spending some time in Chester Depot, Bonnie's Bundles Dolls and DaVallia Art & Accents are top sights worth seeing.

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Stay near popular Chester attractions

Bonnie's Bundles Dolls

7.6/10 (4 reviews)

This historic Vermont studio showcased handcrafted cloth dolls with embroidered faces and calico clothing. Visitors treasured personal interactions with artist Bonnie Watters and stories behind her creations.

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DaVallia Art & Accents

10.0/10 (2 reviews)

This Vermont art haven showcases fine local art and handcrafted furniture in thoughtfully designed spaces. Browse both the Art Boutique and 39 North Gallery to experience indoor exhibits and outdoor sculpture gardens.

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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 Chester Hotel Reviews

Woodstock Inn & Resort

10/10 Excellent

"Clean rooms, very friendly staff, noise AC"

Grand Summit Resort, A Vail Resorts Property

10/10 Excellent

"1"

On The River Inn

10/10 Excellent

"Everyone was so friendly and the food at breakfast and dinner was excellent! Looking forward to coming back next year!"

The Palmer House Resort, an Ascend Collection Hotel

8/10 Good

"Older property that needs updating. Beds were very comfortable."

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent

"Great place to stay"

The Jackson

10/10 Excellent

"Amazing stay and great restaurant!"

Hampton Inn and Suites Manchester

10/10 Excellent

"The staff were very nice, room was clean, and the breakfast was good. All made for an easy night as we traveled through Manchester."

Aspen At Manchester

10/10 Excellent

"Great place, but a bit over priced for what it is"

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"By far, our favorite place to stay at as a family. The staff is always very friendly, courteous and kind, and the property is breathtaking. The views of the mountains and the foliage were absolutely stunning. The rooms are spacious and well taken care of. We especially enjoyed the hot tubs with the Mountain View."

More cheap stays in Chester

The Putney Inn

57 Putney Landing Rd Putney VT

S$118

25 Oct - 26 Oct

includes taxes & fees

8.4/10 Very good! (1,005 reviews)

The Manchester View

77 High Meadow Way & VT-7A Manchester Center VT

S$119

5 Nov - 6 Nov

includes taxes & fees

Aspen At Manchester

5669 Main Street Manchester Center VT

S$159

2 Nov - 3 Nov

includes taxes & fees

8.8/10 Excellent! (699 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

S$165

2 Nov - 3 Nov

includes taxes & fees

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT

S$206

1 Nov - 2 Nov

includes taxes & fees

9.6/10 Exceptional! (1,004 reviews)

Latchis Hotel

50 Main Street Brattleboro VT

S$249

7 Oct - 8 Oct

includes taxes & fees

Frequently asked questions

Where is the best place to stay in Chester?

Based on our traveller data, Fullerton Inn is one of the top choices for your stay. This inn offers free breakfast and a restaurant. Stone Hearth Inn and Eatery is another good choice for your visit. See all available top hotels, or vacation rentals in Chester.

If I need to cancel my hotel reservation in Chester, will I receive a refund?

Yes! The majority of hotel reservations are fully refundable if cancelled prior to the hotel's cancellation deadline, which is often 24 or 48 hours before your check-in date. If your reservation is non-refundable, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

What's the best dog-friendly accommodation option in Chester?

Motel in the Meadow is a top dog-friendly option for your stay. See more pet-friendly hotel accommodations in Chester.

What are some accommodation options with pools in Chester?

Woodstock Inn & Resort: Features a seasonal outdoor pool, an indoor pool and 4 restaurants. Aspen At Manchester and The Manchester View are two additional hotels that feature an on-site pool. View all hotels with pools in Chester.

What is staying in Chester like?

Visitors to Chester will definitely enjoy the skiing, cafes and shopping. Quaint and relaxing, this city also attracts tourists with its restaurants. In Chester, there are 67 hotels and other accommodation options to choose from. Find out more about Chester.

What should I do while I'm visiting Chester?

A couple of favourite places to visit are DaVallia Art & Accents and Bonnie's Bundles Dolls. You'll also find Vermont Country Store and Lowell Lake State Park in the area. Take a look at what more there is to see and do in Expedia's Chester guide.

What's the weather like in Chester?

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.

Chester Hotels from S$89

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chester hotels

1. Fullerton Inn

2. Stone Hearth Inn and Eatery

3. Best Western Springfield Hotel

4. Pointe at Castle Hill Resort

5. Harvest Barn Inn

6. The Manchester View

7. The Upper Pass Lodge at Magic Mountain

8. Bromley View Inn

9. The Inn at Weathersfield

10. Claremont Motor Lodge

11. Blue Gentian Lodge at Magic Mountain

12. Sleep Woodstock Motel

13. Jackson Gore Village, A Vail Resorts Property

14. The Hartness House

15. Four Columns Inn

16. The Common Man Inn & Restaurant

17. The Putney Inn

18. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

19. Sun Lodge near Manchester VT, Ascend Collection Hotel

20. Castle Hill Resort And Spa

Where to stay in Chester

Chester Depot

Stay near popular Chester attractions

Bonnie's Bundles Dolls

DaVallia Art & Accents

Learn more about Chester

Top Chester Hotel Reviews

Woodstock Inn & Resort

Grand Summit Resort, A Vail Resorts Property

On The River Inn

The Palmer House Resort, an Ascend Collection Hotel

The Black Bear Lodge at Stratton Mountain Resort

The Jackson

Hampton Inn and Suites Manchester

Aspen At Manchester

Jackson Gore Village, A Vail Resorts Property

More cheap stays in Chester

The Putney Inn

The Manchester View

Aspen At Manchester

Keene Elm City Hotel, an Ascend Collection Hotel

Hampton Inn and Suites Manchester

Latchis Hotel

Frequently asked questions

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