Chester Hotels from €83 - Fully Refundable Options

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Go beyond your typical stay in Chester

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Our top choices for Chester hotels

A building with a modern design, featuring large windows and a covered outdoor seating area.

A lobby with a stone wall, wooden staircase, and a reception desk.

A hotel room with two beds, a wooden headboard, a desk, and a window with a view of greenery.

A spacious dining area with high ceilings and large windows, featuring wooden tables and chairs, a piano, and a view of the outside.

1. The Mountain Inn at Killington

Killington

Daniel

€138

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.

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

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

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

2. Pointe at Castle Hill Resort

Cavendish

Cristian

€146

includes taxes & fees

18 Oct - 19 Oct

An indoor dining area with multiple wooden tables and chairs, surrounded by lush greenery and a stone water feature.

A spacious lobby with a stone fireplace, leather sofas, and a wooden coffee table.

A spacious indoor dining area with multiple wooden tables and chairs, surrounded by various plants and trees.

An indoor swimming pool with a curved design, surrounded by seating areas and plants.

3. Fireside Inn & Suites West Lebanon

West Lebanon

amanda

€136

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

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

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

4. Stone Hearth Inn and Eatery

Chester

John

€274

includes taxes & fees

12 Oct - 13 Oct

A spacious living room with a stone fireplace, leather sofas, a coffee table, and large arched windows offering views of the outdoors.

A hotel bathroom with a granite countertop, a sink, a mirror, and a wicker basket with towels.

An indoor swimming pool with clear water, surrounded by lounge chairs and a tiled floor.

A patio with two wicker chairs and a table, surrounded by greenery and a white structure.

5. Align Inn Vermont

Quechee

Bruce

€122

includes taxes & fees

1 Nov - 2 Nov

A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.

A two-story house with a balcony, surrounded by lush greenery and a pond.

A two-story house with a snow-covered roof and a front porch.

A kitchen with white tiled backsplash, wooden crates, and hanging pendant lights.

6. On The River Inn

West Woodstock

SARAH

€180

includes taxes & fees

1 Nov - 2 Nov

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

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

7. Fullerton Inn

Chester Depot

kris

€126

includes taxes & fees

9 Nov - 10 Nov

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

A spacious living area with a staircase, patterned sofas, a coffee table, and a decorative wall piece.

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.

8. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

Shannon

€150

includes taxes & fees

1 Nov - 2 Nov

A circular room with lockers, benches, and a wooden ceiling.

A patio area with a fire pit, outdoor seating, and a swimming pool.

A spacious loft-style living area with high ceilings, exposed wooden beams, and a mezzanine level.

A large, multi-story hotel with a prominent entrance and a staircase leading to the upper levels.

9. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington

Richard

€141

includes taxes & fees

2 Nov - 3 Nov

A room with a checkered floor, a bench, and a fireplace.

A spacious room with large windows, a fireplace, and comfortable seating areas.

A rustic dining area with wooden beams, a chandelier, and a kitchen in the background.

A large, white building with a symmetrical facade, multiple windows, and a central entrance with steps.

10. Woodstock Inn & Resort

Woodstock

Ann

€451

includes taxes & fees

10 Nov - 11 Nov

A calm lake surrounded by autumn-colored trees and a clear blue sky.

A cozy living room with a stone fireplace, leather sofas, a round coffee table, and a large window offering a view of the outdoors.

A bar area with wooden stools, pendant lighting, and a rustic ceiling.

A wooden dock with two Adirondack chairs and a blanket, overlooking a calm lake with dense forest in the background.

11. Mountain Meadows Lodge

Killington

Kathy

€177

includes taxes & fees

27 Oct - 28 Oct

A red building with a stone fire pit and outdoor seating.

A row of red-roofed buildings with a central entrance and a grassy field in the foreground.

A cozy lobby with a stone fireplace, leather sofas, and a staircase.

A stone fireplace with a fire, flanked by two leather armchairs and a small table with a plate of food and wine glasses.

12. Grand Summit Resort, A Vail Resorts Property

West Dover

Daniel

€160

includes taxes & fees

9 Nov - 10 Nov

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

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

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.

13. Castle Hill Resort And Spa

Cavendish

Brandon

€262

includes taxes & fees

19 Oct - 20 Oct

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.

14. The Hartness House

Springfield

Elizabeth

€197

includes taxes & fees

8 Nov - 9 Nov

A two-story house with a snow-covered yard and a well-lit front porch.

A park with a paved walkway, a small pond, and various trees.

Two people in a swimming pool with inflatable rings.

A room with two patterned chairs, a table with a lamp, a mirror, and a framed picture on the wall.

15. Golden Stage Inn B&B

Cavendish

"The Golden Stage Inn was one of the highlights of our Vermont trip. Mike and Julie are wonderful hosts and have clearly put so much care into making the entire experience special. Our room was cozy, spacious, and beautifully kept, with a fireplace, lovely bathroom, and one of the most comfortable beds we’ve slept in while traveling. Breakfast alone is a reason to stay here. The two-course breakfasts were phenomenal, with fresh, local ingredients, juice, and plenty of coffee, all served in a...

Andrew

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.

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

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

16. Best Western Springfield Hotel

Springfield

Dzmitry

€149

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.

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

17. The Inn at Weathersfield

Perkinsville

Dorrie

€253

includes taxes & fees

5 Nov - 6 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.

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A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

Top Chester Hotel Reviews

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."

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent

"Beautiful place for getaway!!!😊"

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."

Pointe at Castle Hill Resort

8/10 Good

"Nice facility. Clean and convenient."

Hampton Inn and Suites Manchester

10/10 Excellent

"Great location and staff is AWESOME! Thanks for another pleasant stay!!"

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"

Hideaway Inn Mt. Snow

10/10 Excellent

"This place was great! Super cute and clean"

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

€83

25 Oct - 26 Oct

includes taxes & fees

The Manchester View

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

€99

3 Nov - 4 Nov

includes taxes & fees

9.4/10 Exceptional! (925 reviews)