Top 10 Hotels in Chester, VT from ₩124,061 - Competitive Prices

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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

kris

₩172,894

₩188,454 total

includes taxes & fees

Nov 10 - Nov 11

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.

2. Stone Hearth Inn and Eatery

Chester

John

₩377,986

₩412,004 total

includes taxes & fees

Oct 13 - Oct 14

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 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.

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

3. Best Western Springfield Hotel

Springfield

Dzmitry

₩203,867

₩224,254 total

includes taxes & fees

Nov 1 - Nov 2

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

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

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

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

4. Pointe at Castle Hill Resort

Cavendish

Cristian

₩192,741

₩219,725 total

includes taxes & fees

Oct 18 - Oct 19

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

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

5. The Hartness House

Springfield

Elizabeth

₩270,277

₩297,303 total

includes taxes & fees

Nov 10 - Nov 11

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.

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

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

6. The Inn at Weathersfield

Perkinsville

Dorrie

₩303,850

₩380,517 total

includes taxes & fees

Nov 5 - Nov 6

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

7. Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area

Jessica

₩247,519

₩300,728 total

includes taxes & fees

Nov 10 - Nov 11

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 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.

8. Harvest Barn Inn

Bellows Falls

gail

₩203,914

₩222,266 total

includes taxes & fees

Nov 1 - Nov 2

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.

9. Castle Hill Resort And Spa

Cavendish

Brandon

₩360,664

₩393,124 total

includes taxes & fees

Oct 19 - Oct 20

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.

10. The Common Man Inn & Restaurant

Claremont

Bruce

₩173,698

₩188,468 total

includes taxes & fees

Nov 1 - Nov 2

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.

11. The Upper Pass Lodge at Magic Mountain

Londonderry

Terry

₩128,344

₩146,953 total

includes taxes & fees

Oct 15 - Oct 16

A two-story building with a patio area featuring outdoor seating and a stone fire pit.

A swimming pool with a lifeguard chair, pool lift, and a seating area with chairs and tables.

A treats display with snacks and sundries.

A spacious living area with a fireplace, comfortable seating, and a stone accent wall.

12. Hampton Inn and Suites Manchester

Manchester Center

Rosemary

₩203,921

₩224,313 total

includes taxes & fees

Nov 1 - Nov 2

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 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.

A bar area with a hexagonal tiled wall, a wooden planter with greenery, a metal tray with cookies, and a menu board on the wall.

13. Main and Mountain Bar & Motel

Ludlow

Patricia

₩270,679

₩297,752 total

includes taxes & fees

Oct 19 - Oct 20

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 house with a balcony and a garden with red flowers.

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

14. Blue Gentian Lodge at Magic Mountain

Londonderry

Abigail

₩199,699

₩219,669 total

includes taxes & fees

Nov 3 - Nov 4

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

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

15. Claremont Motor Lodge

Claremont

Alastair

₩160,831

₩174,502 total

includes taxes & fees

Oct 18 - Oct 19

A spacious lobby with a reception desk, seating area, and a modern ceiling light fixture.

A hotel room with two beds, a microwave, a coffee maker, and a small kitchenette.

A hotel entrance with a modern design, featuring a prominent entrance canopy and stone pillars.

A spacious lobby with modern furniture, a large digital map display, and a high ceiling with geometric lighting.

16. Holiday Inn Express Hotel & Suites Brattleboro by IHG

Brattleboro

Timothy

₩198,358

₩218,194 total

includes taxes & fees

Nov 8 - Nov 9

A two-story house with a red exterior and white trim. There are three large windows on the front and a chimney on the right side.

A spacious living room with wooden beams, a patterned sofa, a yellow armchair, and a red door.

A cozy living room with a fireplace, wooden furniture, and large windows.

A dining table set for four with a view of a garden through large windows.

17. COHO Inn & Motor Lodge

Weston

Raedene

₩275,021

₩299,776 total

includes taxes & fees

Oct 15 - Oct 16

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

A white house with a porch, wooden chairs, and umbrellas.

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.

18. The Weston

Weston

LISA

₩529,403

₩577,049 total

includes taxes & fees

Oct 20 - Oct 21

A hotel room with a brick wall, a large bed with white bedding, a flat-screen TV, and a desk with a lamp.

A bar area with a fireplace, seating, and a TV.

A living room with a brick wall, two armchairs, a sofa, a coffee table, and a patterned rug.

19. Fairfield Inn & Suites by Marriott Keene Downtown

Keene

Caroline

₩232,401

₩252,155 total

includes taxes & fees

Oct 25 - Oct 26

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 view through a sliding glass door.

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

20. The Manchester View

Manchester Center

Jan

₩135,701

₩149,271 total

includes taxes & fees

Nov 3 - Nov 4

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Where to stay in Chester

Find the best Chester areas and neighborhoods for the activities you enjoy most.Learn more about Chester

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

Hampton Inn and Suites Manchester

10/10 Excellent

"Perfect for our one night stay. Rooms were clean. Staff were friendly and helpful. Restaurants within walkable distance."

The Manchester View

8/10 Good

"Beautiful room, very clean and new. It was very bare in the room though. Breakfast from 8-10 and we went at 9:40, it was wiped out with nobody refilling so make sure you go early. Next day we went early and it was delicious! Hot tub was amazing which we used both nights. Overall, the views are gorgeous and highly recommend this hotel."

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."

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."

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."

Colonial Motel

8/10 Good

"very convenient and cost was good, as we stay in Brattleboro as our daughter and granddaughter live in Turners Falls Mass. and its only a half hour drive to visit with them."

Stone Hearth Inn and Eatery

8/10 Good

"Breakfast was very nice and staff very friendly… unfortunately it is not very accessible if you have walking difficulties … all the bedrooms are on the second floor and there are no elevators… l wish l had known this before l had booked the room …. we stayed 1 night even though we had reserved 2 nights because of the difficulty of the stairs… It was however nice if no handicaps"

More cheap stays in Chester

The Putney Inn

57 Putney Landing Rd Putney VT

₩112,783

₩124,061 total

Oct 26 - Oct 27

includes taxes & fees

The Manchester View

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

₩135,701

₩149,271 total

Nov 3 - Nov 4

includes taxes & fees

9.4/10 Exceptional! (927 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd Keene NH

₩159,491

₩173,048 total

Nov 2 - Nov 3

includes taxes & fees

8.6/10 Excellent! (1,006 reviews)

Aspen At Manchester

5669 Main Street Manchester Center VT

₩165,790

₩197,098 total

Nov 2 - Nov 3

includes taxes & fees

8.8/10 Excellent! (701 reviews)

Latchis Hotel

50 Main Street Brattleboro VT

₩189,982

₩208,981 total

Nov 1 - Nov 2

includes taxes & fees

Hampton Inn and Suites Manchester

4519 Main St Manchester Center VT

₩203,921

₩224,313 total

Nov 1 - Nov 2

includes taxes & fees

9.6/10 Exceptional! (1,009 reviews)

Frequently asked questions

Where is the best place to stay in Chester?

Based on our traveler 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 stay. 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 provided that you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If you have a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

Where can I learn more about changing or cancelling my trip to Chester?

For additional details about rescheduling or cancelling your trip to Chester, head over to our customer service page.

What's the best pet-friendly accommodation in Chester?

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

What are some accommodations 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 with an onsite pool. View all hotels with pools in Chester.

What's the best accommodation near Hartness State Airport (VSF)?

The Inn at Weathersfield is a popular 4-star inn featuring free breakfast and a restaurant. It's located a short 1.3 mi (2.1 km) from Hartness State Airport. Another good choice close to the airport is Hartness House Inn, located 3.7 mi (5.9 km) away.

What is staying in Chester like?

Visitors to Chester are sure to enjoy the ski areas, coffeehouses, and shopping. Quaint and relaxing, this city also attracts tourists with its restaurants. In Chester, there are 67 hotels and other accommodations to choose from. Find out more about Chester.

What should I see while I'm in Chester?

A couple of favorite 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. Check out what more 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 temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.

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Book Hotels in Chester on Expedia.com

Find hotels in Chester, VT from ₩124,061

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. The Hartness House

6. The Inn at Weathersfield

7. Jackson Gore Village, A Vail Resorts Property

8. Harvest Barn Inn

9. Castle Hill Resort And Spa

10. The Common Man Inn & Restaurant

11. The Upper Pass Lodge at Magic Mountain

12. Hampton Inn and Suites Manchester

13. Main and Mountain Bar & Motel

14. Blue Gentian Lodge at Magic Mountain

15. Claremont Motor Lodge

16. Holiday Inn Express Hotel & Suites Brattleboro by IHG

17. COHO Inn & Motor Lodge

18. The Weston

19. Fairfield Inn & Suites by Marriott Keene Downtown

20. The Manchester View

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

Hampton Inn and Suites Manchester

The Manchester View

Hideaway Inn Mt. Snow

Best Western Plus Keene Hotel

Woodstock Inn & Resort

The Black Bear Lodge at Stratton Mountain Resort

Aspen At Manchester

Colonial Motel

Stone Hearth Inn and Eatery

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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