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Check availability on Chester 4 Star Hotels

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Chester 4-star hotels

A room with a checkered floor, a bench, and a fireplace.
A large, white building with a symmetrical facade, multiple windows, and a central entrance with steps.
A spacious living room with a grand chandelier, large windows, and a comfortable seating area.
A spacious room with large windows, a fireplace, and comfortable seating areas.

1. Woodstock Inn & Resort

Woodstock Inn & Resort
Woodstock
United States
Ann
10.865.508 ₫
13.093.067 ₫ total
includes taxes & fees
10 Nov - 11 Nov
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 cozy room with a wooden bench, a chair, and a sofa. There are large windows with wooden frames and a chandelier hanging from the ceiling.
A two-story house with a porch, American flags, and a well-maintained garden.

2. The Jackson

The Jackson
West Woodstock
United States
Ava
3.194.822 ₫
3.514.304 ₫ total
includes taxes & fees
3 Nov - 4 Nov
The Jackson
A fire pit with flames, surrounded by outdoor seating and string lights.
A living room with a sofa, armchair, and a table with books.
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.

3. Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG
Manchester Village Historic District
United States
Ian
4.875.216 ₫
6.446.695 ₫ total
includes taxes & fees
10 Nov - 11 Nov
Kimpton Taconic Hotel by IHG
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.
Two people toasting with drinks on a balcony overlooking a large building with columns.
A spacious hotel lobby with a high ceiling, chandeliers, seating areas, and large windows.

4. The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa
Manchester Village Historic District
United States
Maryalice
2.461.461 ₫
4.071.020 ₫ total
includes taxes & fees
11 Nov - 12 Nov
The Equinox Golf Resort And Spa
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 spacious living room with a large American flag, a fireplace, and a chandelier.
A kitchen with white tiled backsplash, wooden crates, and hanging pendant lights.

5. On The River Inn

On The River Inn
West Woodstock
United States
SARAH
4.231.584 ₫
5.225.298 ₫ total
includes taxes & fees
3 Nov - 4 Nov
On The River Inn
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 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.

6. Four Columns Inn

Four Columns Inn
Newfane
United States
Raymond
2.772.650 ₫
3.022.189 ₫ total
includes taxes & fees
2 Nov - 3 Nov
Four Columns Inn
A restaurant with tables set for dining, chairs, and a fireplace in the background.
A bedroom with a large bed, bedside tables, a small bench, and a sofa in the corner.
A room with a brown leather sofa, a wooden chest labeled "The Honorable Lieutenant Captain Greenwood's Bay," and two windows with floral curtains.
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.

7. The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant
Manchester Village Historic District
United Kingdom
Tracey
5.938.428 ₫
6.532.271 ₫ total
includes taxes & fees
25 Oct - 26 Oct
The Reluctant Panther Inn and Restaurant
A rustic lodge with stone walls, a stone fireplace, and outdoor seating.
A spacious kitchen with wooden cabinets, a large island, and pendant lighting.
A wooden double door with a 'Welcome' sign above it, a deer sculpture to the right, and a lantern on the left.
A rustic interior with a stone fireplace, leather sofas, wooden tables, and a large mural on the wall.

8. Seesaw's Lodge

Seesaw's Lodge
Peru
5.746.303 ₫
6.263.470 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Seesaw's Lodge
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 living room with a sofa, ottoman, armchair, and a television on a stand.
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
5.879.044 ₫
7.362.456 ₫ total
includes taxes & fees
5 Nov - 6 Nov
The Inn at Weathersfield
A multi-story residential building with a central courtyard.
A multi-story residential building with wooden balconies and a stone foundation.
A living room with a high arched window, a fireplace, a television, and a bookshelf.
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
Kathia
Winterplace at Okemo, A Vail Resorts Property
A spacious dining area with a high ceiling, stone walls, and a fireplace.
A bar area with a long counter and multiple stools, a fireplace with a mantel, and a yellow armchair.
A round wooden table set outdoors with white chairs, two glasses of wine, and a potted plant.
A white building with a green roof and a stone wall in the foreground.

11. The Hermitage Inn Vermont

The Hermitage Inn Vermont
West Dover
United States
Theresa
9.627.255 ₫
10.589.980 ₫ total
includes taxes & fees
24 Oct - 25 Oct
The Hermitage Inn Vermont
A wooden deck with a solar panel, surrounded by lush greenery and a hill in the background.
A stone pathway leading to a porch with a wooden railing, surrounded by lush greenery and a lattice fence.
A room with a stone fireplace, large windows with curtains, a patterned rug, and a plush chair.
A large, white, two-story house with a steeply pitched roof, a balcony, and a staircase leading to the upper floor.

12. Windham Hill Inn

Windham Hill Inn
West Townshend
United States
Nadine
4.578.489 ₫
4.990.553 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Windham Hill Inn
A large, two-story house with a snow-covered driveway and surrounding trees.
An outdoor dining area with tables and chairs, umbrellas, and a view of a forested landscape.
A cozy room with a brick fireplace, floral wallpaper, and comfortable seating.
A cozy living room with a fireplace, leather chairs, a sofa, and a table with wine glasses.

13. Chesterfield Inn

Chesterfield Inn
West Chesterfield
United States
Wayne
7.809.162 ₫
8.473.021 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Chesterfield 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 spacious living room with leather sofas, a stone fireplace, and a large window offering a view.
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 dining area with a round wooden table, white chairs, and a green wall.
A room with a chessboard, leather chairs, a large vase, and a bookshelf.
A cozy living room with a piano, leather sofa, armchair, and a globe on a coffee table.

15. Inn on Putney Road

Inn on Putney Road
Brattleboro
United States
Karla
6.921.769 ₫
7.613.894 ₫ total
includes taxes & fees
1 Nov - 2 Nov
Inn on Putney Road
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.

16. The Village Inn of Woodstock

The Village Inn of Woodstock
Woodstock
United States
Sam
The Village Inn of Woodstock
A white building with green shutters, a brick chimney, and a picket fence.
A bedroom with a wooden ceiling, a large bed, a rocking chair, and a sofa.
A building with green shutters and flower boxes filled with various flowers.
A wooden table with a stack of magazines and a vase with pink flowers.

17. The Woodstocker B&B

The Woodstocker B&B
Woodstock
United States
Kavina
The Woodstocker B&B
A large, multi-story house with a symmetrical roofline, a central staircase, and a well-maintained lawn.
A swimming pool with lounge chairs and tables, surrounded by trees and a stone wall.
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.

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

Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
Cavendish
Castle Hill Resort Condo: 5 Mi to Slopes at Okemo!
A balcony with a wicker chair, a wooden railing, and a view of a forested area.
A living room with a fireplace, a television, and a lamp.
A rectangular swimming pool with a tiled edge, surrounded by lounge chairs and umbrellas, with a building in the background.
A playground with slides and climbing structures surrounded by trees.

19. 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
A patio with a table and chairs, a red umbrella, and a decorative metal pot.
A living room with a leather sofa, a wooden coffee table, and a television.
A modern two-story house with large windows, a patio with outdoor furniture, and a well-maintained lawn.
A cozy living area with a leather sofa, a wooden bench, and a small table.

20. West Dover Townhome: Hot Tub, 1 1/2 m to Mount sno

West Dover Townhome: Hot Tub, 1 1/2 m to Mount sno
West Dover
West Dover Townhome: Hot Tub, 1 1/2 m to Mount sno
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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
10.243.140 ₫
11.165.023 ₫ total
20 Oct - 21 Oct
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

On The River Inn

On The River Inn

10/10 Excellent
"Karen at the front desk was absolutely delightful. She saw me struggling with my dog and bags, and helped me to my room. Dan on the housekeeping was so nice. We saw him almost every day. The hotel is incredibly pet friendly. It's so convenient to walk out of your room directly onto the rear lawn, and down toward the river. I had a nice chat with the lady who lives across the river. She also has a dog. The drive to downtown was just a few minutes. I highly recommend the farmer's market (you pass it on the way to downtown Woodstock). The room was very clean. The sink and bathroom door could use some updates, but other than that it was lovely. I would definitely return again with my pup."
VS 4-night trip
Posted 7 days ago
On The River Inn

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.
  • Search for the lowest price from 11.165.023 ₫
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 accommodation, 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 accommodation 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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