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

4 Stars Hotels in Chester, Vermont from CA $213

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester 4 Star Hotels

Tonight
Aug 26 - Aug 27
Tomorrow
Aug 27 - Aug 28
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Chester 4-star hotels

Lobby
Sauna, hot tub, steam room, body treatments, aromatherapy
Interior
4 restaurants; breakfast, lunch, and dinner served

1. Woodstock Inn & Resort

Woodstock Inn & Resort
Woodstock
United States
ben
CA $566
CA $684 total
includes taxes & fees
Sep 7 - Sep 8
Woodstock Inn & Resort
Meeting facility
Breakfast and dinner served
Seasonal outdoor pool
Exterior

2. Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG
Manchester Village Historic District
United States
Ronda
CA $303
CA $391 total
includes taxes & fees
Sep 9 - Sep 10
Kimpton Taconic Hotel by IHG
House (Meadow) | View from room
Lobby sitting area
Lobby
Property amenity

3. The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa
Manchester Village Historic District
United States
Gabriel
CA $214
CA $312 total
includes taxes & fees
Sep 7 - Sep 8
The Equinox Golf Resort And Spa
Hallway
Daily buffet breakfast for a fee
Exterior
Front of property

4. On The River Inn

On The River Inn
West Woodstock
United Kingdom
Laura
CA $317
CA $379 total
includes taxes & fees
Sep 10 - Sep 11
On The River Inn
Restaurant
View from room
Exterior
Lobby sitting area

5. The Jackson

The Jackson
West Woodstock
United States
Brian
CA $248
CA $272 total
includes taxes & fees
Aug 31 - Sep 1
The Jackson
Restaurant
Superior Room
Outdoor dining
Property entrance

6. The Reluctant Panther Inn and Restaurant

The Reluctant Panther Inn and Restaurant
Manchester Village Historic District
United States
Jamie
CA $335
CA $369 total
includes taxes & fees
Sep 2 - Sep 3
The Reluctant Panther Inn and Restaurant
Land view from property
Staircase
Garden
Lobby sitting area

7. Four Columns Inn

Four Columns Inn
Newfane
United States
John
CA $195
CA $213 total
includes taxes & fees
Aug 31 - Sep 1
Four Columns Inn
Exterior
Dining
Property entrance
Interior

8. Seesaw's Lodge

Seesaw's Lodge
Peru
United States
Mira
CA $301
CA $328 total
includes taxes & fees
Sep 3 - Sep 4
Seesaw's Lodge
Interior
Front of property
Terrace/patio
King Room with Garden View

9. The Inn at Weathersfield

The Inn at Weathersfield
Perkinsville
United States
Rula
CA $264
CA $339 total
includes taxes & fees
Sep 3 - Sep 4
The Inn at Weathersfield
Terrace/patio
Bar (on property)
Front of property
Room 3 | Bathroom

10. The Village Inn of Woodstock

The Village Inn of Woodstock
Woodstock
United States
Sam
The Village Inn of Woodstock
Property grounds
Indoor pool
Exterior
Winter Place Two Bedroom plus Loft Ski In/Out

11. 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
Front of property - evening/night
Lobby
Standard King Room
Dinner served

12. Chesterfield Inn

Chesterfield Inn
West Chesterfield
United States
Wayne
CA $591
CA $641 total
includes taxes & fees
Sep 1 - Sep 2
Chesterfield Inn
Room, 1 Queen Bed, Garden View | Mountain view
Romantic Room, 1 King Bed
Exterior
Exterior

13. Windham Hill Inn

Windham Hill Inn
West Townshend
United States
Nadine
CA $257
CA $280 total
includes taxes & fees
Sep 8 - Sep 9
Windham Hill Inn
Exterior
Interior detail
Soundproofing, iron/ironing board (on request), individually decorated
View from property

14. The Woodstocker B&B

The Woodstocker B&B
Woodstock
United States
Kavina
The Woodstocker B&B
Exterior
Room, 6 Bedrooms (Home) | Dining room
Dining room
Room, 6 Bedrooms (Home) | Living area

15. 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
Exterior
Dining
Flat-screen TV, DVD player
Interior detail

16. Inn on Putney Road

Inn on Putney Road
Brattleboro
United States
Karla
CA $408
CA $449 total
includes taxes & fees
Sep 1 - Sep 2
Inn on Putney Road
Restaurant
Food and drink
Front of property
Exterior

17. The Hermitage Inn Vermont

The Hermitage Inn Vermont
West Dover
United States
Keely
CA $414
CA $455 total
includes taxes & fees
Aug 31 - Sep 1
The Hermitage Inn Vermont
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior
Apartment (3 Bedrooms) | Interior

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!
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior

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
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior
Apartment (2 Bedrooms) | Interior

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!
Save an average of 15% on thousands of hotels when you're signed in

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 $823
CA $897 total
Aug 29 - Aug 30
includes taxes & fees
10/10 Exceptional! (11 reviews)
The Weston
Still don't see what you're looking for?
See all properties in Chester.
You can also use these popular filters to refine your search.
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

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 $897
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.

Explore a world of travel with Expedia