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4 Stars Hotels in Chester, Vermont from CA $150

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Check availability on Chester 4 Star Hotels

Tonight
Oct 11 - Oct 12
Tomorrow
Oct 12 - Oct 13
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

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
CA $597
CA $720 total
includes taxes & fees
Nov 10 - Nov 11
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 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.

2. The Jackson

The Jackson
West Woodstock
United States
Ava
CA $176
CA $193 total
includes taxes & fees
Nov 3 - Nov 4
The Jackson
A fire pit with flames, surrounded by outdoor seating and string lights.
A restaurant with wooden tables and chairs, large windows, and a chandelier.
A white building with a covered entrance, surrounded by white chairs arranged in rows, and string lights overhead.
A living room with a sofa, armchair, and a table with books.

3. Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG
Manchester Village Historic District
United States
Ian
CA $268
CA $354 total
includes taxes & fees
Nov 8 - Nov 9
Kimpton Taconic Hotel by IHG
A covered patio area with a wicker sofa, a round table with drinks, and a chair.
A spacious hotel lobby with a high ceiling, chandeliers, seating areas, and large windows.
A room with a fireplace, a sofa, a dining table with chairs, and large windows offering a view of the outside.
Two people toasting with drinks on a balcony overlooking a large building with columns.

4. The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa
Manchester Village Historic District
United States
Maryalice
CA $128
CA $215 total
includes taxes & fees
Nov 11 - Nov 12
The Equinox Golf Resort And Spa
A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.
A spacious living room with a large American flag, a fireplace, and a chandelier.
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.

5. On The River Inn

On The River Inn
West Woodstock
United States
SARAH
CA $233
CA $287 total
includes taxes & fees
Nov 1 - Nov 2
On The River Inn
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.
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.
A living room with leather sofas, a round ottoman, a fireplace, and a bookshelf.

6. Four Columns Inn

Four Columns Inn
Newfane
United States
Raymond
CA $137
CA $150 total
includes taxes & fees
Nov 2 - Nov 3
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 two-story building with a porch, American flag, and two white rocking chairs.
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
CA $326
CA $359 total
includes taxes & fees
Oct 25 - Oct 26
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 two-story wooden cabin with a stone foundation, large windows, and a wooden porch.
A wooden double door with a 'Welcome' sign above it, a deer sculpture to the right, and a lantern on the left.

8. Seesaw's Lodge

Seesaw's Lodge
Peru
United States
Michaela
CA $316
CA $344 total
includes taxes & fees
Oct 18 - Oct 19
Seesaw's Lodge
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 living room with a sofa, ottoman, armchair, and a television on a stand.
A large, multi-story building with a symmetrical facade, multiple chimneys, and a well-maintained garden with evergreen trees.

9. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Dorrie
CA $304
CA $384 total
includes taxes & fees
Nov 5 - Nov 6
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 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.
A white pergola with a stone pathway leading to a house.

11. The Hermitage Inn Vermont

The Hermitage Inn Vermont
West Dover
United States
Theresa
CA $492
CA $541 total
includes taxes & fees
Oct 30 - Oct 31
The Hermitage Inn Vermont
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 room with a stone fireplace, large windows with curtains, a patterned rug, and a plush chair.
A stone pathway leading to a porch with a wooden railing, surrounded by lush greenery and a lattice fence.

12. Windham Hill Inn

Windham Hill Inn
West Townshend
United States
Nadine
CA $252
CA $274 total
includes taxes & fees
Oct 22 - Oct 23
Windham Hill Inn
A large, two-story house with a snow-covered driveway and surrounding trees.
A cozy room with a brick fireplace, floral wallpaper, and comfortable seating.
An outdoor dining area with tables and chairs, umbrellas, and a view of a forested landscape.
A bedroom with a large bed, a blue armchair, a wooden desk, and a view through a glass door.

13. Chesterfield Inn

Chesterfield Inn
West Chesterfield
United States
Wayne
CA $429
CA $466 total
includes taxes & fees
Oct 18 - Oct 19
Chesterfield Inn
A large, multi-story building with a symmetrical facade, surrounded by a well-maintained lawn and wildflowers.
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 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.

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
CA $381
CA $419 total
includes taxes & fees
Nov 1 - Nov 2
Inn on Putney Road
A man serving drinks at an outdoor table with a white tablecloth, surrounded by guests.
A large, two-story house with a snow-covered roof and a porch with string lights.
A room with a fireplace, a table with a teapot and cup, and a mirror above the fireplace.
A bar area with a wooden counter, various bottles, glasses, and a menu.

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 wooden table with a stack of magazines and a vase with pink flowers.
A building with green shutters and flower boxes filled with various 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.
An aerial view of a residential property with a tennis court, swimming pool, and multiple houses.
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.

18. 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 balcony with a wicker chair, a wooden railing, and a view of a forested area.
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.
A house with a purple front door, a small porch, and a gravel driveway.

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 modern two-story house with large windows, a patio with outdoor furniture, and a well-maintained lawn.
A kitchen with wooden cabinets, a microwave, an oven, and a bar area with stools.
A living room with a leather sofa, a wooden coffee table, and a television.

20. West Dover Townhome: Hot Tub, 2 Mi to Mount Snow!

West Dover Townhome: Hot Tub, 2 Mi to Mount Snow!
West Dover
West Dover Townhome: Hot Tub, 2 Mi to Mount Snow!
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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
CA $467
CA $509 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

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 5 days ago
On The River Inn

Find out more about Chester

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Chester are calling your name. Known for providing first-rate service in amazing locations, each of the Chester 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Chester. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Chester, Vermont, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Chester hotels with 4 Stars provide everything you need to unwind in style.

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 fits your budget, take advantage of Expedia's filter tool. Check out the availability during your chosen dates and use our pricing filter to set your maximum rate. You can also list your results by the most budget-friendly retreat first.
  • Search for the lowest price from CA $509
What's the difference between 5-star and 4-star hotels in Chester?
Offering a welcoming guest experience and upmarket décor, 4-star hotels are an excellent option for your Chester trip. These types of accommodations generally come with lots of handy amenities that make it easy to kick back and relax — think complimentary bathrobes, gyms and restaurants. Or enjoy even more lavishness at a 5-star hotel designed to indulge you in high-end perks and amenities. 24-hour front desk, complimentary toiletries and gourmet dining are typically featured at these swanky retreats.
Does Chester have any 4-star all-inclusive resorts?
Finding your dream vacation in Chester is as easy as typing in your travel details and selecting our "All inclusive" filter. Stay and play where everything is already taken care of like your accommodations, meals and activities, or opt for a standard 4-star resort in or around this popular destination.

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