𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Chester (2026)

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Pet friendly

Apartment

Pool

Condo

Hot tub

Spa

Cottage

Family friendly

Waterpark

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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 bedroom with a bed, a bedside table, a lamp, a mirror, a dresser, a window, and a ceiling fan.

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

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

1. Fullerton Inn

Chester Depot

kris

S$180

includes taxes & fees

10 Nov - 11 Nov

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

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

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

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

2. Stone Hearth Inn and Eatery

Chester

John

S$335

includes taxes & fees

19 Oct - 20 Oct

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.

3. Pointe at Castle Hill Resort

Cavendish

Cristian

S$210

includes taxes & fees

18 Oct - 19 Oct

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

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

A hotel room with a bed, a sitting area, a bathroom with a bathtub, and a large mirror.

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

4. Best Western Springfield Hotel

Springfield

Dzmitry

S$214

includes taxes & fees

1 Nov - 2 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 living room with a fireplace, a sofa, a coffee table, and a dining area with chairs and a table.

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

5. The Upper Pass Lodge at Magic Mountain

Londonderry

Terry

S$148

includes taxes & fees

15 Oct - 16 Oct

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

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

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.

6. Harvest Barn Inn

Bellows Falls

gail

S$189

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 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.

7. Bromley View Inn

Bondville

BARBARA

S$114

includes taxes & fees

1 Nov - 2 Nov

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

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

A large, multi-story building with a symmetrical facade, multiple chimneys, and a well-maintained garden with evergreen trees.

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

8. The Inn at Weathersfield

Perkinsville

Dorrie

S$348

includes taxes & fees

5 Nov - 6 Nov

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

A building with a 'Public Welcome' sign, a vending machine, and a hanging flower basket.

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

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

9. Claremont Motor Lodge

Claremont

Alastair

S$147

includes taxes & fees

18 Oct - 19 Oct

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

A living room with a fireplace, a sofa, a coffee table, a cabinet, and two chairs.

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.

10. The Manchester View

Manchester Center

Jan

S$143

includes taxes & fees

3 Nov - 4 Nov

A calm lake reflecting a forest with autumn foliage.

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

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.

11. Blue Gentian Lodge at Magic Mountain

Londonderry

Abigail

S$210

includes taxes & fees

3 Nov - 4 Nov

A modern bedroom with two beds, wooden headboards, a bench, a small table, and a large window with a view of greenery.

A bedroom with a bed, a wooden pegboard wall with books and a guitar, and a TV mounted on the wall.

A person performing yoga on a wooden deck overlooking a river with trees in the background.

A living room with a sofa, a coffee table, a red chair, a lamp, and a patterned rug.

12. Otherland Hotel

Newfane

Omar

S$244

includes taxes & fees

15 Oct - 16 Oct

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

13. Four Columns Inn

Newfane

Raymond

S$133

includes taxes & fees

3 Nov - 4 Nov

A red building with a gravel driveway and a large tree.

An aerial view of a residential area with houses, a tennis court, and a swimming pool.

A cozy interior with a bar area, wooden furniture, and a Christmas tree.

A spacious room with high ceilings, wooden beams, large windows, and tables and chairs arranged for dining.

14. The Landgrove

Londonderry

Lisa

S$225

includes taxes & fees

9 Nov - 10 Nov

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

A golf course with rolling hills, trees, and a distant mountain range.

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

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

15. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area

Jessica

S$287

includes taxes & fees

10 Nov - 11 Nov

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

A banquet hall with multiple round tables set for dining, featuring chandeliers and brick walls.

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

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

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 stone facade with a wooden door, steps leading up to a porch, and a small white chair outside.

17. The Hartness House

Springfield

Elizabeth

S$284

includes taxes & fees

10 Nov - 11 Nov

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

A dining area with a wooden table and chairs, a window with a view, and a bookshelf with books and decorative items.

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

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

18. Sun Lodge near Manchester VT, Ascend Collection Hotel

Bromley Mountain

Lynn

S$168

includes taxes & fees

1 Nov - 2 Nov

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

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

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.

19. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

Shannon

S$215

includes taxes & fees

1 Nov - 2 Nov

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

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.

A spacious living room with a fireplace, comfortable seating, and a large window providing natural light.

20. Castle Hill Resort And Spa

Cavendish

Brandon

S$331

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

Hideaway Inn Mt. Snow

8/10 Good

"Hard to find the hot tub. Strange to not have staff there."

Best Western Plus Keene Hotel

8/10 Good

"The hotel needs some updating, and could be a little cleaner. Bathroom door looked like it had not been cleaned in a long time. The staff was friendly, and breakfast was good."

Hampton Inn and Suites Manchester

8/10 Good

"Clean rooms and convenient morning breakfast. Laundry on property."

Woodstock Inn & Resort

10/10 Excellent

"Room was spacious and very clean upon arrival. Staff was also very attentive and took care all our needs."

Pointe at Castle Hill Resort

8/10 Good

"Room was adequate. Bedding was uncomfortable. We would not revisit this property. We would not recommend to others."

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent

"It's a great place to stay! I've been there several times in different seasons. Off-season or leaf peeper season the free breakfast is a lot less than the free breakfast during ski season. During ski season AKA winter, eggs, waffles, pancakes etc however during other seasons they only offer cold cereal, milk bagels toast and juice and coffee of course. Other than that it's a fantastic place and they're dog friendly"

Aspen At Manchester

10/10 Excellent

"This was the first time I've ever stayed in a hotel where you arrive and go straight to your room without having to check in at a front desk first. The instructions via email or text (whichever it was) for how to do so were clear and we had no problems getting into our room. The location was convenient and the property itself was very nice."

Latchis Hotel

10/10 Excellent

"For being a historic hotel this place was nice. Sound machines in the rooms to make up for being on a busy street. Fan in the room to help with circulation. Historic charm in great walkable downtown location. Parking lot was small but there is additional parking in a city lot and on the street."

The Manchester View

10/10 Excellent

"We loved this property, our view opened up to magnificent Mountain View, if you are there during lead peeping season you know that makes a difference. We enjoyed the hot tub at night and the fireplace . Kind staff, they left cookies and bowls for our dog, breakfast was delicious, the variety of baked goods was perfect and the Vermont coffee provided brought up to a higher level I can’t wait to go back for a longer stay"

More cheap stays in Chester

The Putney Inn

57 Putney Landing Rd Putney VT

S$119

25 Oct - 26 Oct

includes taxes & fees

The Manchester View

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

S$143

3 Nov - 4 Nov

includes taxes & fees

9.4/10 Exceptional! (925 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

S$165

2 Nov - 3 Nov

includes taxes & fees

8.6/10 Excellent! (1,004 reviews)

Aspen At Manchester

5669 Main Street Manchester Center VT

S$188

2 Nov - 3 Nov

includes taxes & fees

8.8/10 Excellent! (700 reviews)

Latchis Hotel

50 Main Street Brattleboro VT

S$200

1 Nov - 2 Nov

includes taxes & fees

8.6/10 Excellent! (1,010 reviews)

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT

S$214

1 Nov - 2 Nov

includes taxes & fees

9.6/10 Exceptional! (1,007 reviews)

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$119

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. Pointe at Castle Hill Resort

4. Best Western Springfield Hotel

5. The Upper Pass Lodge at Magic Mountain

6. Harvest Barn Inn

7. Bromley View Inn

8. The Inn at Weathersfield

9. Claremont Motor Lodge

10. The Manchester View

11. Blue Gentian Lodge at Magic Mountain

12. Otherland Hotel

13. Four Columns Inn

14. The Landgrove

15. Jackson Gore Village, A Vail Resorts Property

16. The Common Man Inn & Restaurant

17. The Hartness House

18. Sun Lodge near Manchester VT, Ascend Collection Hotel

19. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

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

Hideaway Inn Mt. Snow

Best Western Plus Keene Hotel

Hampton Inn and Suites Manchester

Woodstock Inn & Resort

Pointe at Castle Hill Resort

The Black Bear Lodge at Stratton Mountain Resort

Aspen At Manchester

Latchis Hotel

The Manchester View

More cheap stays in Chester

The Putney Inn

The Manchester View

Keene Elm City Hotel, an Ascend Collection Hotel

Aspen At Manchester

Latchis Hotel

Hampton Inn and Suites Manchester

Frequently asked questions

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