A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

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Check availability on Chester 4 Star Hotels

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Sep 30 - Oct 1
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Oct 1 - Oct 2
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Oct 2 - Oct 4
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Oct 9 - Oct 11

Our top choices for Chester 4-star hotels

A room with a checkered floor, a bench, and a fireplace.
A spacious living room with a grand chandelier, large windows, and a comfortable seating area.
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.

1. Woodstock Inn & Resort

Woodstock Inn & Resort
Woodstock
United States
Ann
$709 nightly
$780 total
Oct 27 - Oct 28
Total with taxes and fees
Woodstock Inn & Resort
A spacious room with a stone fireplace, leather furniture, and large windows offering a view of greenery.
A two-story house with a porch, American flags, and a well-maintained garden.
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.

2. The Jackson

The Jackson
West Woodstock
United States
Laura
$245 nightly
$269 total
Oct 26 - Oct 27
Total with taxes and fees
The Jackson
A fire pit with flames, surrounded by outdoor seating and string lights.
A white building with a covered entrance, surrounded by white chairs arranged in rows, and string lights overhead.
A restaurant with wooden tables and chairs, large windows, and a chandelier.
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
Richard
$301 nightly
$331 total
Oct 29 - Oct 30
Total with taxes and fees
Kimpton Taconic Hotel by IHG
A covered patio area with a wicker sofa, a round table with drinks, and a chair.
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.
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
$210 nightly
$231 total
Oct 27 - Oct 28
Total with taxes and fees
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 balcony, surrounded by lush greenery and a pond.
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 Kingdom
Laura
$257 nightly
$283 total
Oct 26 - Oct 27
Total with taxes and fees
On The River Inn
A white colonial-style building with a symmetrical facade, central entrance, and a small porch with chairs.
A long wooden table with red placemats and multiple wine glasses arranged for a tasting.
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.

6. Four Columns Inn

Four Columns Inn
Newfane
United States
Raymond
$238 nightly
$259 total
Oct 11 - Oct 12
Total with taxes and fees
Four Columns Inn
A restaurant with tables set for dining, chairs, and a fireplace in the background.
A two-story building with a porch, American flag, and two white rocking chairs.
A bedroom with a large bed, bedside tables, a small bench, and a sofa in the corner.
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 States
Jamie
$229 nightly
$252 total
Oct 18 - Oct 19
Total with taxes and fees
The Reluctant Panther Inn and Restaurant
A rustic lodge with stone walls, a stone fireplace, and outdoor seating.
A wooden double door with a 'Welcome' sign above it, a deer sculpture to the right, and a lantern on the left.
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.

8. Seesaw's Lodge

Seesaw's Lodge
Peru
United States
Michaela
$222 nightly
$242 total
Oct 5 - Oct 6
Total with taxes and fees
Seesaw's Lodge
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 large, multi-story building with a symmetrical facade, multiple chimneys, and a well-maintained garden with evergreen trees.
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
Rula
$260 nightly
$284 total
Oct 27 - Oct 28
Total with taxes and fees
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 multi-story residential building with wooden balconies and a stone foundation.
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
Keely
$367 nightly
$404 total
Oct 24 - Oct 25
Total with taxes and fees
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 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
$207 nightly
$225 total
Oct 20 - Oct 21
Total with taxes and fees
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 bedroom with a large bed, a blue armchair, a wooden desk, and a view through a glass door.
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
$301 nightly
$327 total
Oct 18 - Oct 19
Total with taxes and fees
Chesterfield Inn
A large, multi-story building with a symmetrical facade, surrounded by a well-maintained lawn and wildflowers.
A dining area with a long wooden table, wooden chairs, and a decorative centerpiece.
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.

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 room with a chessboard, leather chairs, a large vase, and a bookshelf.
A living room with a fireplace, a pool table, and comfortable seating.
A dining area with a round wooden table, white chairs, and a green wall.

15. Inn on Putney Road

Inn on Putney Road
Brattleboro
United States
Karla
Inn on Putney Road
A man serving drinks at an outdoor table with a white tablecloth, surrounded by guests.
A bar area with a wooden counter, various bottles, glasses, and a menu.
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.
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 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.
An aerial view of a residential property with a tennis court, swimming pool, and multiple houses.
A gym with various exercise machines, wooden walls, and a large mirror.
A swimming pool with lounge chairs and tables, surrounded by trees and a stone wall.

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 house with a purple front door, a small porch, and a gravel driveway.
A rectangular swimming pool with a tiled edge, surrounded by lounge chairs and umbrellas, with a building in the background.
A living room with a fireplace, a television, and a lamp.

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 cozy living area with a leather sofa, a wooden bench, and a small table.
A kitchen with wooden cabinets, a microwave, an oven, and a bar area with stools.

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
$395 nightly
$431 total
Oct 20 - Oct 21
Total with taxes and 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
"Garden and grounds out back were very nice. Restaurant provided great dinner and breakfast."
Rick 2-night trip
Posted 2 days ago
The Jackson
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"all was wonderful and well orchestrated"
Peter 3-night trip
Posted 3 days ago
Kimpton Taconic Hotel by IHG

Find out more about Chester

The beginning of any much-needed holiday kicks off with selecting a location. Chester has been a popular destination with tourists because it offers so much. Yet, "location, location, location" applies to more than just what city where your plane lands. Now that you have a feeling for the area, it is time you to learn a little more about your new digs.

Properties as Picturesque as Chester

Chester saw its fair share of visitors this past year. Our review section provides reviews that highlight how astounding these rooms are. The hotels found here strive to make your vacation as pleasant as your evenings exploring Chester. These hotels work to make the facilities and grounds hospitable from the minute you step out of your car. You won't need to venture far to keep up with your workout schedule, enjoy a refreshing plunge, or find a nice meal during your stay with everything they provide.

Rooms have been configured to keep your utmost comfort in mind, with amenities like premium bedding, and in-room tea or coffee, and designer bathroom products. So, lay back and decompress. Moreover, if you find yourself in need of anything further, you can trust the staff will try their best to ensure you remain pleased during your time there. These properties are so nice that you'll regret the day you have to leave.

Book a 4-Star Hotel in Chester Today!

A vacation to Chester should be one where you won't have to be concerned about the little things. Of course, your getaway should be all about getting the most out of your destination. And getting the most means giving yourself the very best. Expedia has 4-star hotels that allow you to do just that. Book through Expedia today!

Frequently asked questions

How much does it cost to stay in a 4-star hotel in Chester?
With Expedia's handy search filters, bagging a terrific deal on a 4-star hotel in Chester just got simpler. Start by keying in your chosen arrival date and length of your break. Then sort the results by price and pick a hotel that best fits your style and budget.
  • Search for the lowest price from $431
What's the difference between 5-star and 4-star hotels in Chester?
Offering an inviting traveler experience and upscale décor, 4-star hotels are a great option for your Chester trip. These kinds of accommodations generally feature lots of handy amenities that make it easy to unpack and unwind — think 24-hour room service, restaurants and pools. Or get a taste of the high life at a 5-star hotel designed to indulge you in exclusive perks and amenities. On-site health clubs, complimentary toiletries and gourmet dining are typically included at these deluxe retreats.
Does Chester have any 4-star all-inclusive resorts?
Use our "All inclusive" filter to find your next dream getaway in Chester where just about everything is taken care of, from your accommodations to your meals, activities and entertainment. We can also help you find standard 4-star stays in and around this destination.

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