𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Chester (2026)

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Pet friendly

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Pool

Hot tub

Condo

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

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

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

Tim

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 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

John

S$291

includes taxes & fees

16 Nov - 17 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.

A sign for Castle Hill Spa surrounded by lush greenery and a well-maintained lawn.

3. Pointe at Castle Hill Resort

Cavendish

Cristian

S$222

includes taxes & fees

28 Oct - 29 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

Bryan

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

5. The Upper Pass Lodge at Magic Mountain

Londonderry

Lynne

S$139

includes taxes & fees

19 Nov - 20 Nov

A calm lake reflecting a forest with autumn foliage.

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

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.

6. Blue Gentian Lodge at Magic Mountain

Londonderry

Abigail

S$191

includes taxes & fees

4 Nov - 5 Nov

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

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.

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

7. The Inn at Weathersfield

Perkinsville

Dorrie

S$338

includes taxes & fees

5 Nov - 6 Nov

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 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.

8. The Manchester View

Manchester Center

Jan

S$143

includes taxes & fees

3 Nov - 4 Nov

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

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 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.

9. Bromley View Inn

Bondville

BARBARA

S$133

includes taxes & fees

21 Oct - 22 Oct

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

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

A row of cabins with a river in the foreground, surrounded by trees and a snowy landscape.

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

10. Sleep Woodstock Motel

Woodstock

Dave

S$160

includes taxes & fees

18 Nov - 19 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 spacious living area with a staircase, patterned sofas, a coffee table, and a decorative wall piece.

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

11. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

Sara

S$215

includes taxes & fees

27 Oct - 28 Oct

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

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.

A store interior with shelves stocked with various products, a refrigerated display case, and a wall sign.

12. Otherland Hotel

Newfane

Omar

S$202

includes taxes & fees

21 Oct - 22 Oct

A large two-story house with a front porch and a well-maintained lawn.

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

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

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

13. The Landgrove

Londonderry

Alan

S$231

includes taxes & fees

1 Nov - 2 Nov

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

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

Lynn

S$154

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.

15. The Hartness House

Springfield

Zhenchun

S$270

includes taxes & fees

19 Nov - 20 Nov

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

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

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

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

16. Claremont Motor Lodge

Claremont

Marguerite

S$152

includes taxes & fees

17 Nov - 18 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 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.

17. Four Columns Inn

Newfane

Raymond

S$136

includes taxes & fees

3 Nov - 4 Nov

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

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

18. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area

Adriana

S$287

includes taxes & fees

18 Nov - 19 Nov

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 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.

19. Harvest Barn Inn

Bellows Falls

gail

S$266

includes taxes & fees

29 Oct - 30 Oct

A spacious living area with a high ceiling, a wooden staircase, and a built-in kitchen visible through an open door.

A spacious living room with a wooden staircase, a television, a sofa set, and a fireplace.

A living room with a sofa, a coffee table, a chess table, a TV, and a gaming console.

A building with a covered outdoor area, wooden benches, and potted plants.

20. Brittany Motel

Manchester Center

Keith

S$121

includes taxes & fees

2 Nov - 3 Nov

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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

Pointe at Castle Hill Resort

8/10 Good

"The hotel was clean but older. Nothing special. Basic hotel room."

Grand Summit Resort, A Vail Resorts Property

10/10 Excellent

"The hotel was built in the 1990’s per the concierge, which surprised us, as it is so well maintained that it seems much newer! We booked a king bed room with (small) balcony. Our only complaint would be the bathroom toilet situation. Toilet is very small and way too close to the door…a very awkward setup, especially trying to get into the shower. The tub and shower however seemed completely new. Very nice! The room is quite large and the bed was very comfortable. I’m only 4’10” so it was a high hurdle for me, so I made up the couch bed and slept there. I usually bring a small folding stool but forgot it, so the couch bed was a nice option…it seems to be new and was comfortable. The first night we ate at the hotel restaurant and everything was very tasty, especially the Brussel sprouts and salmon. We were celebrating my husband’s birthday weekend, and brought wine but had to drink from coffee mugs as the hotel is “green” so no cups in the room. We snagged a couple cups from the restaurant for our second night. 😊 Also there’s no mini fridge. We had breakfast twice at 1MTN restaurant, which we highly recommend! Second night we had dinner at “Ten Tables”…their Berkshire Pork Chop was PHENOMENAL. 3rd night we drove down to Wilmington to “The Anchor”…every single thing was delicious! We had a superb weekend!"

Hampton Inn and Suites Manchester

10/10 Excellent

"Clean, close to central area, great breakfast 😁 no complaints!"

Colonial Motel

8/10 Good

"The rooms are quite large. There were a lot of unfinished projects going on, so the property was messy and slightly unkempt. The breakfast was terrible. Trash bags were left out attracting skunks. Price made it a 4 star."

Best Western Plus Keene Hotel

10/10 Excellent

"Excellent place to stay"

Hideaway Inn Mt. Snow

8/10 Good

"It was a tablet check in which was fairly easy but sends the room number and access code to your e mail address . The rooms were clean and tidy. Free hot drinks in an area on a lower floor. Check out didn’t work on the tablet, so used the telephone. Nobody answered that call, but a member of staff appeared and said everything was fine and we could leave. Diving distance to local restaurants and there were numerous. The gondola was close by, although we didn’t go to the top because it was raining hard and didn’t think we would see much."

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent

"Everything was good; but continental breakfast was poor; there was no eggs"

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent

"Beautiful resort with amazing beds! Very comfortable."

Fullerton Inn

10/10 Excellent

"Stayed there 7yrs.ago and had another great experience this time, Cloe our waitress was excellent and made our dining alot of fun."

More cheap stays in Chester

The Putney Inn

57 Putney Landing Rd Putney VT

S$118

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

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

S$176

28 Oct - 29 Oct

includes taxes & fees

Aspen At Manchester

5669 Main Street Manchester Center VT

S$188

2 Nov - 3 Nov

includes taxes & fees

Latchis Hotel

50 Main Street Brattleboro VT

S$199

4 Nov - 5 Nov

includes taxes & fees

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT

S$214

1 Nov - 2 Nov

includes taxes & fees

9.6/10 Exceptional! (1,008 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$118

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. Blue Gentian Lodge at Magic Mountain

7. The Inn at Weathersfield

8. The Manchester View

9. Bromley View Inn

10. Sleep Woodstock Motel

11. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

12. Otherland Hotel

13. The Landgrove

14. Sun Lodge near Manchester VT, Ascend Collection Hotel

15. The Hartness House

16. Claremont Motor Lodge

17. Four Columns Inn

18. Jackson Gore Village, A Vail Resorts Property

19. Harvest Barn Inn

20. Brittany Motel

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

Pointe at Castle Hill Resort

Grand Summit Resort, A Vail Resorts Property

Hampton Inn and Suites Manchester

Colonial Motel

Best Western Plus Keene Hotel

Hideaway Inn Mt. Snow

The Black Bear Lodge at Stratton Mountain Resort

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Fullerton Inn

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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