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Chester 4 Stars Hotels

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Check availability on Chester 4 Star Hotels

Tonight
Oct 22 - Oct 23
Tomorrow
Oct 23 - Oct 24
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Chester 4-star hotels

A room with a checkered floor, a bench, and a fireplace.
A rustic dining area with wooden beams, a chandelier, and a kitchen in the background.
A spacious room with large windows, a fireplace, and comfortable seating areas.
A large, white building with a symmetrical facade, multiple windows, and a central entrance with steps.

1. Woodstock Inn & Resort

Woodstock Inn & Resort
Woodstock
United States
Ann
NT$11,966
NT$14,589 total
includes taxes & fees
Nov 16 - Nov 17
Woodstock Inn & Resort
A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.
A well-maintained lawn with a central garden area, a brick building, and a view of a forested hill.
A two-story house with a porch, American flags, and a well-maintained garden.
A bedroom with a large window, a bed, a chair, and a lamp.

2. The Jackson

The Jackson
West Woodstock
United States
Ava
NT$3,995
NT$4,395 total
includes taxes & fees
Nov 16 - Nov 17
The Jackson
A covered patio area with a wicker sofa, a round table with drinks, and a chair.
A large indoor swimming pool with wooden beams and a central decorative element.
A room with a fireplace, a sofa, a dining table with chairs, and large windows offering a view of the outside.
A spacious hotel lobby with a high ceiling, chandeliers, seating areas, and large windows.

3. The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa
Manchester Village Historic District
United States
Maryalice
NT$3,600
NT$5,688 total
includes taxes & fees
Nov 22 - Nov 23
The Equinox Golf Resort And Spa
A fire pit with flames, surrounded by outdoor seating and string lights.
A living room with a beige armchair, a small round table, a wooden bookcase, and patterned curtains.
A restaurant with wooden tables and chairs, large windows, and a chandelier.
A living room with a sofa, armchair, and a table with books.

4. Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG
Manchester Village Historic District
United States
Jim
NT$6,031
NT$7,990 total
includes taxes & fees
Nov 22 - Nov 23
Kimpton Taconic Hotel by IHG
A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.
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.
A spacious living room with a large American flag, a fireplace, and a chandelier.

5. On The River Inn

On The River Inn
West Woodstock
United States
SARAH
NT$5,291
NT$6,469 total
includes taxes & fees
Nov 11 - Nov 12
On The River Inn
A restaurant with tables set for dining, chairs, and a fireplace in the background.
An outdoor dining area with a table set for six, surrounded by wicker chairs, in a garden setting with hanging planters and a lamp post.
A two-story building with a porch, American flag, and two white rocking chairs.
A room with a brown leather sofa, a wooden chest labeled "The Honorable Lieutenant Captain Greenwood's Bay," and two windows with floral curtains.

6. The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant
Manchester Village Historic District
United States
Jeffrey
NT$7,426
NT$8,168 total
includes taxes & fees
Oct 28 - Oct 29
The Reluctant Panther Inn and Restaurant
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.
A serene pond with a statue in the center, surrounded by lush greenery and trees.
A living room with leather sofas, a round ottoman, a fireplace, and a bookshelf.
A spacious living area with a staircase, a red door, and a large window.

7. Four Columns Inn

Four Columns Inn
Newfane
United States
Raymond
NT$3,467
NT$3,779 total
includes taxes & fees
Nov 2 - Nov 3
Four Columns Inn
A spacious dining area with a high ceiling, stone walls, and a fireplace.
A white building with a green roof and a stone wall in the foreground.
A round wooden table set outdoors with white chairs, two glasses of wine, and a potted plant.
A bar area with a long counter and multiple stools, a fireplace with a mantel, and a yellow armchair.

8. The Hermitage Inn Vermont

The Hermitage Inn Vermont
West Dover
United States
Theresa
NT$12,039
NT$13,242 total
includes taxes & fees
Oct 30 - Oct 31
The Hermitage Inn Vermont
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.

9. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Dorrie
NT$7,352
NT$9,206 total
includes taxes & fees
Nov 5 - Nov 6
The Inn at Weathersfield
A multi-story residential building with a central courtyard.
A living room with a high arched window, a fireplace, a television, and a bookshelf.
A private property entrance with a sign indicating it is for residents and guests only, with a speed limit sign of 15 mph.
An indoor swimming pool with clear water, surrounded by green chairs and large windows offering views of trees.

10. Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property
Clock Tower Base Area
United States
Lori A.
Winterplace at Okemo, A Vail Resorts Property
A rustic lodge with stone walls, a stone fireplace, and outdoor seating.
A rustic interior with a stone fireplace, leather sofas, wooden tables, and a large mural on the wall.
A two-story wooden cabin with a stone foundation, large windows, and a wooden porch.
A spacious kitchen with wooden cabinets, a large island, and pendant lighting.

11. Seesaw's Lodge

Seesaw's Lodge
Peru
United States
Michaela
NT$5,131
NT$5,593 total
includes taxes & fees
Nov 2 - Nov 3
Seesaw's Lodge
A man serving drinks at an outdoor table with a white tablecloth, surrounded by guests.
A room with a fireplace, a table with a teapot and cup, and a mirror above the fireplace.
A person holding two plates of food in a kitchen.
A large, two-story house with a snow-covered roof and a porch with string lights.

12. The Village Inn of Woodstock

The Village Inn of Woodstock
Woodstock
United States
Sam
The Village Inn of Woodstock
A wooden deck with a solar panel, surrounded by lush greenery and a hill in the background.
A kitchen with wooden cabinets, a built-in stove, a microwave, and a sink.
A large, white, two-story house with a steeply pitched roof, a balcony, and a staircase leading to the upper floor.
A room with a stone fireplace, large windows with curtains, a patterned rug, and a plush chair.

13. Windham Hill Inn

Windham Hill Inn
West Townshend
United States
Nadine
Windham Hill Inn
A large, multi-story building with a symmetrical facade, surrounded by a well-maintained lawn and wildflowers.
A dining area with a wooden table, chairs, and a chandelier. There is a window with blinds, a plant, and a view of the outside.
A kitchen with wooden cabinets, a stainless steel refrigerator, a large island with stools, and a window with decorative curtains.
A dining area with a long wooden table, wooden chairs, and a decorative centerpiece.

14. Solitude Village at Okemo by Vail Resorts

Solitude Village at Okemo by Vail Resorts
Clock Tower Base Area
United States
DIEN
Solitude Village at Okemo by Vail Resorts
A large, white, two-story house with a dark roof, surrounded by lush greenery and a gravel pathway.
A cozy living room with a piano, leather sofa, armchair, and a globe on a coffee table.
A living room with a fireplace, a pool table, and comfortable seating.
A room with a chessboard, leather chairs, a large vase, and a bookshelf.

15. Inn on Putney Road

Inn on Putney Road
Brattleboro
United States
Karla
NT$8,655
NT$9,521 total
includes taxes & fees
Nov 5 - Nov 6
Inn on Putney Road
A large, two-story house with a snow-covered driveway and surrounding trees.
A cozy living room with a fireplace, leather chairs, a sofa, and a table with wine glasses.
A bedroom with a large bed, a blue armchair, a wooden desk, and a view through a glass door.
A cozy room with a brick fireplace, floral wallpaper, and comfortable seating.

16. Chesterfield Inn

Chesterfield Inn
West Chesterfield
United States
Wayne
NT$9,765
NT$10,595 total
includes taxes & fees
Nov 8 - Nov 9
Chesterfield Inn
A large, multi-story house with a symmetrical roofline, a central staircase, and a well-maintained lawn.
A gym with various exercise machines, wooden walls, and a large mirror.
An aerial view of a residential property with a tennis court, swimming pool, and multiple houses.
A patio with a table and chairs, a screen door, and a view of a grassy area with trees.

17. Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!

Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
Cavendish
United States
Nipa
Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
A white building with green shutters, a brick chimney, and a picket fence.
Two wooden chairs with red cushions on a porch with a striped rug, a small wooden table, and a view of trees and a white fence in the background.
A building with green shutters and flower boxes filled with various flowers.
A bedroom with a wooden ceiling, a large bed, a rocking chair, and a sofa.

18. The Woodstocker B&B

The Woodstocker B&B
Woodstock
United States
Kavina
The Woodstocker B&B
A wooden deck with Adirondack chairs, a snow-covered ground, and a view of a lodge with a mountain backdrop.
A living room with a sofa, a wooden coffee table, a brown armchair, and a plaid rug.
An indoor swimming pool with clear glass walls, a tiled ceiling, and a sunlit room with windows and a reception area.
A courtyard with a wooden staircase leading to a building entrance, surrounded by greenery and large rocks.

19. 'bearfoot Apres' Mtn-view Condo < 1 Mi to Mt Snow!

'bearfoot Apres' Mtn-view Condo < 1 Mi to Mt Snow!
West Dover
'bearfoot Apres' Mtn-view Condo < 1 Mi to Mt Snow!
A balcony with a wicker chair, a wooden railing, and a view of a forested area.
A house with a purple front door, a small porch, and a gravel driveway.
A playground with slides and climbing structures surrounded by trees.
A rectangular swimming pool with a tiled edge, surrounded by lounge chairs and umbrellas, with a building in the background.

20. Bromley Mountain Escape w/ 2 Balconies: Hike & Ski

Bromley Mountain Escape w/ 2 Balconies: Hike & Ski
Bromley Mountain
United States
Chris
Bromley Mountain Escape w/ 2 Balconies: Hike & Ski
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Chester.
The Weston

The Weston

630 Main St Weston VT
NT$12,809
NT$13,961 total
Nov 1 - Nov 2
includes taxes & fees
The Weston
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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

The Jackson

The Jackson

10/10 Excellent
"Quaint and elegant property. Thebinsite restaurant was great. Enjoyed our 1 night stay here at The Jackson."
Clarissa 1-night trip
Posted 2 days ago
The Jackson

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Chester?
To book a 4-star hotel in Chester that matches your budget, make use of Expedia's sort and search filters. Check out what's available during your getaway dates and use our pricing filter to set your maximum rate. You can also sort your results by the most economical property first.
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What's the difference between 5-star and 4-star hotels in Chester?
Give yourself the luxury treatment during your Chester getaway by choosing a 4-star hotel. As well as featuring upscale accommodations, these properties are usually packed with amenities like bathrobes, large beds and more. A 5-star hotel will go the extra mile to make your trip an even more lavish and memorable one. Concierge assistance, luxurious spas and gourmet dining are a few of the first-rate conveniences and services you'll likely have access to.
Does Chester have any 4-star all-inclusive resorts?
Use our "All inclusive" filter to search for your next escape in Chester where just about everything is taken care of, from your accommodations to your food, activities and entertainment. We can also help you find standard 4-star stays in and around this sought-after destination.

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