𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Chester (2026)

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Pet friendly

Apartment

Hot tub

Condo

Pool

Spa

Cottage

Family friendly

Waterpark

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Our top choices for Chester hotels

Hotel

Motel

Breakfast included

Bed & breakfast

Pet friendly

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

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

1. Fullerton Inn

Chester Depot

Kirsty

S$193

includes taxes & fees

1 Sept - 2 Sept

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

2. Stone Hearth Inn and Eatery

Chester

Olena

S$278

includes taxes & fees

24 Aug - 25 Aug

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

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

3. Best Western Springfield Hotel

Springfield

Gerry

S$225

includes taxes & fees

27 Aug - 28 Aug

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

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

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

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

4. The Hartness House

Springfield

Dan

S$248

includes taxes & fees

26 Aug - 27 Aug

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

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.

5. The Upper Pass Lodge at Magic Mountain

Londonderry

Terry

S$121

includes taxes & fees

2 Sept - 3 Sept

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

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.

6. Harvest Barn Inn

Bellows Falls

Michael

S$227

includes taxes & fees

31 Aug - 1 Sept

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.

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

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

7. Pointe at Castle Hill Resort

Cavendish

Stephen

S$181

includes taxes & fees

3 Sept - 4 Sept

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 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.

8. Bromley View Inn

Bondville

William

S$107

includes taxes & fees

24 Aug - 25 Aug

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

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

9. Claremont Motor Lodge

Claremont

Shane

S$149

includes taxes & fees

24 Aug - 25 Aug

A calm lake reflecting a forest with autumn foliage.

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

10. Blue Gentian Lodge at Magic Mountain

Londonderry

Abigail

S$202

includes taxes & fees

31 Aug - 1 Sept

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

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

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

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

11. The Inn at Weathersfield

Perkinsville

Rula

S$313

includes taxes & fees

23 Aug - 24 Aug

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

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

12. The Common Man Inn & Restaurant

Claremont

Denis

S$185

includes taxes & fees

23 Aug - 24 Aug

A two-story building with a bar and restaurant on the ground floor, a vintage car parked in front, and a sign indicating "Main Mountain".

A bar area with a long counter, green upholstered bar stools, and a variety of bottles and glasses on shelves.

A modern hotel room with a bed, a seating area with a chair and a small table, a TV mounted on the wall, and a window with curtains.

13. Main and Mountain Bar & Motel

Ludlow

Kristina

S$204

includes taxes & fees

31 Aug - 1 Sept

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

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

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

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

14. Sun Lodge near Manchester VT, Ascend Collection Hotel

Bromley Mountain

Charlene

S$178

includes taxes & fees

13 Sept - 14 Sept

A large, multi-story hotel with a central courtyard featuring a pond and a fountain.

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

A bar area with a wooden counter and stools, large windows with a view of a snowy landscape, and a ceiling with recessed lighting.

A multi-story building with a central staircase, outdoor seating area, and a view of the sunset.

15. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

Gene

S$173

includes taxes & fees

23 Aug - 24 Aug

A white two-story house with a front porch, a covered patio, and a well-maintained garden.

A bathroom with a glass shelf holding toiletries, a vase with sunflowers, and a window with blinds.

A living room with a sofa, a coffee table, and a painting on the wall.

A dining table with plates of food, two glasses of white wine, and a bottle of wine.

16. The Weston

Weston

LISA

S$366

includes taxes & fees

24 Aug - 25 Aug

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

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

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

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

17. Four Columns Inn

Newfane

John

S$204

includes taxes & fees

14 Sept - 15 Sept

A hotel room with two beds, a window with blinds, a desk with a television, and a lamp.

A reception desk with a wooden finish, a small plant, and a seating area with tables and chairs.

A lobby with a stone fireplace, leather sofas, and a reception desk.

A stone wall surrounding a swimming pool with a metal handrail.

18. The Black Bear Lodge at Stratton Mountain Resort

Stratton

Luis

S$199

includes taxes & fees

1 Sept - 2 Sept

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 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.

19. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area

Cynthia

S$285

includes taxes & fees

21 Sept - 22 Sept

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 view through a sliding glass door.

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 chair.

20. The Manchester View

Manchester Center

Edward

S$138

includes taxes & fees

26 Aug - 27 Aug

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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, DaVallia Art & Accents and Bonnie's Bundles Dolls are top sights worth seeing.

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Stay near popular Chester attractions

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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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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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

Claremont Motor Lodge

10/10 Excellent

"My wife and I were very pleased with our stay at the Claremont Motor Lodge. We had a very comfortable stay. We will be stopping here again on our next trip out to Claremont, NH."

On The River Inn

8/10 Good

"Staff was friendly and the room was clean. Nice social atmosphere, game rooms."

Hampton Inn and Suites Manchester

10/10 Excellent

"The room was clean and very comfortable. The amenities were perfect! Breakfast was great!"

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent

"Staff was great. Room was fine. Besides the small bathroom set up and basic continental breakfast, stay was great."

Hampton Inn Brattleboro

10/10 Excellent

"The facility was clean, comfortable and friendly staff"

The Jackson

8/10 Good

"If you are looking for a quiet B & B type experience, a little bit off the beaten path, then this could be a great option for you. Our room was on the second floor with a narrow wooden staircase which made it challenging to bring our multiple bags up to the room. We opted to pull a few necessities out of our main bag and just bring in a carry on, which worked fine. The rooms are lovely and comfortably furnished. The bed was comfortable. One of the "charms" of staying in a B&B type lodging is getting to meet your hosts. We went into town for dinner, so missed the complimentary wine and cheese offering. Other than that, all communication (check-in, questions and checkout) was entirely electronic and we did not see anyone throughout our one-night stay. That felt strange and impersonal to us, but perhaps our expectations were too high. I think we would have been happier in a more traditional hotel setting."

The Palmer House Resort, an Ascend Collection Hotel

8/10 Good

"The property is older, but clean. Staff were very friendly and helpful."

Days Inn by Wyndham Keene NH

8/10 Good

"It was a very pleasant stay"

The Equinox Golf Resort & Spa

10/10 Excellent

"We loved this hotel, really nice amenities, great rooms. I wish we had planned less activities and spent more time at the hotel. If you want to stay in the hotel, plan to spend a day in the hotel. Breakfast ends at 11 and bar closes at around 10 depending on crowd."

More cheap stays in Chester

Days Inn by Wyndham Keene NH

3 Ash Brook Road Keene NH

S$134

16 Sept - 17 Sept

includes taxes & fees

7/10 Good! (1,003 reviews)

Latchis Hotel

50 Main Street Brattleboro VT

S$151

26 Aug - 27 Aug

includes taxes & fees

Hampton Inn Brattleboro

1378 Putney Road Brattleboro VT

S$162

8 Sept - 9 Sept

includes taxes & fees

8.2/10 Very good! (1,014 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

S$166

2 Sept - 3 Sept

includes taxes & fees

8.6/10 Excellent! (1,009 reviews)

Comfort Inn & Suites Brattleboro I-91

1186 Putney Road Brattleboro VT

S$181

31 Aug - 1 Sept

includes taxes & fees

8.6/10 Excellent! (849 reviews)

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT

S$214

30 Aug - 31 Aug

includes taxes & fees

9.6/10 Exceptional! (1,007 reviews)

Frequently asked questions

Where is the best place to stay in Chester?

Located 25.2 mi (40.5 km) from the heart of Chester, Woodstock Inn & Resort is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Keene Elm City Hotel, an Ascend Collection Hotel and Kimpton Taconic Hotel by IHG. 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. Keene Elm City Hotel, an Ascend Collection Hotel and Kimpton Taconic Hotel by IHG 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 62 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$134

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. The Hartness House

5. The Upper Pass Lodge at Magic Mountain

6. Harvest Barn Inn

7. Pointe at Castle Hill Resort

8. Bromley View Inn

9. Claremont Motor Lodge

10. Blue Gentian Lodge at Magic Mountain

11. The Inn at Weathersfield

12. The Common Man Inn & Restaurant

13. Main and Mountain Bar & Motel

14. Sun Lodge near Manchester VT, Ascend Collection Hotel

15. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

16. The Weston

17. Four Columns Inn

18. The Black Bear Lodge at Stratton Mountain Resort

19. Jackson Gore Village, A Vail Resorts Property

20. The Manchester View

Where to stay in Chester

Chester Depot

Stay near popular Chester attractions

DaVallia Art & Accents

Bonnie's Bundles Dolls

Learn more about Chester

Top Chester Hotel Reviews

Claremont Motor Lodge

On The River Inn

Hampton Inn and Suites Manchester

Keene Elm City Hotel, an Ascend Collection Hotel

Hampton Inn Brattleboro

The Jackson

The Palmer House Resort, an Ascend Collection Hotel

Days Inn by Wyndham Keene NH

The Equinox Golf Resort & Spa

More cheap stays in Chester

Days Inn by Wyndham Keene NH

Latchis Hotel

Hampton Inn Brattleboro

Keene Elm City Hotel, an Ascend Collection Hotel

Comfort Inn & Suites Brattleboro I-91

Hampton Inn and Suites Manchester

Frequently asked questions

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