Lodging Image

Search Resort Hotels in Chester from CA $233

  • 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 prices for these dates

Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8
In one month
Nov 20 - Nov 22
In two months
Dec 18 - Dec 20

Our top choices for Chester resorts

A multi-story hotel with a central courtyard and a reflective water feature.

1. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
3.0 star property
Brownsville
9.0 out of 10, Wonderful, (890 reviews)
"Beautiful resort with amazing beds! Very comfortable."
United States
Sara
The price is CA $195
CA $236 total
includes taxes & fees
Oct 28 - Oct 29
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
A hotel room with two beds, a window with blinds, a desk with a television, and a lamp.

2. The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort
3.0 star property
Stratton
7.6 out of 10, Good, (1,008 reviews)
"Great place to stay"
United States
Joseph
The price is CA $193
CA $233 total
includes taxes & fees
Oct 27 - Oct 28
The Black Bear Lodge at Stratton Mountain Resort
A room with a checkered floor, a bench, and a fireplace.

3. Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (621 reviews)
"Wonderful inn! Everything was wonderful: rooms, food, etc!!"
United States
Ann
The price is CA $518
CA $632 total
includes taxes & fees
Nov 16 - Nov 17
Woodstock Inn & Resort
A red building with a stone fire pit and outdoor seating.

4. Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property
3.0 star property
West Dover
8.6 out of 10, Excellent, (325 reviews)
"Great stay most of the rooms are timeshare type rooms for ski season beautiful view good local food Harriman’s food was pretty decent the efficiency apartment was great plenty big enough for two people"
United States
Eben
The price is CA $218
CA $261 total
includes taxes & fees
Oct 28 - Oct 29
Grand Summit Resort, A Vail Resorts Property
A two-story house with a large porch and a pond in front.

5. Deluxe King, kitchenette, fireplace

Deluxe King, kitchenette, fireplace
West Dover
10.0 out of 10, Exceptional, (4 reviews)
"End of season special. Perfect size, fireplace was great on a cold rainy night. Last night restaurant was open for a few weeks."
United States
john L.
The price is CA $338
CA $562 total
includes taxes & fees
Nov 1 - Nov 2
Deluxe King, kitchenette, fireplace
A cozy living room with a fireplace, a dining table set for a meal, and a kitchen in the background.

6. Deluxe King Room w/pull-out love seat and fireplace

Deluxe King Room w/pull-out love seat and fireplace
Dover
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfect"
United States
James R.
The price is CA $338
CA $562 total
includes taxes & fees
Nov 1 - Nov 2
Deluxe King Room w/pull-out love seat and fireplace
A two-story house with a large porch and a pond in front.

7. Deluxe King, Living Room w/sofa bed, bunk bed & fireplace

Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
Dover
9.4 out of 10, Exceptional, (6 reviews)
"This is a beautiful, large suite in a quaint Vermont town. There are two main rooms: a bedroom with a king bed and a bunk bed, and a separate living room with a fireplace. The main inn also has lounge areas open to guests all night, and is a perfect stay for both families and couples. "
United States
Olivia
The price is CA $370
CA $602 total
includes taxes & fees
Nov 1 - Nov 2
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
A two-story white building with a porch, labeled "Farm Road Estate Historic Inn & Cottages."

8. Deluxe King - 2nd floor in Historic Inn

Deluxe King - 2nd floor in Historic Inn
West Dover
The price is CA $305
CA $528 total
includes taxes & fees
Nov 1 - Nov 2
Deluxe King - 2nd floor in Historic Inn
A two-story house with a large porch and a pond in front.

9. Deluxe King- 2nd floor in Historic Inn

Deluxe King- 2nd floor in Historic Inn
West Dover
The price is CA $289
CA $508 total
includes taxes & fees
Nov 1 - Nov 2
Deluxe King- 2nd floor in Historic Inn
A two-story house with a large porch and a pond in front.

10. King with Bunk Bed- 2nd floor in Historic Inn

King with Bunk Bed- 2nd floor in Historic Inn
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Very well apportioned room. Super clean and comfortable. Restaurant was delicious. Bartender is cool to chat with."
United States
Forrest W.
The price is CA $305
CA $528 total
includes taxes & fees
Nov 1 - Nov 2
King with Bunk Bed- 2nd floor in Historic Inn
A two-story house with a large porch and a pond in front.

11. Luxury King w/balcony, accessible

Luxury King w/balcony, accessible
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"My husband and I had a wonderful time at the Inn . our room was beautiful and we had two delicious meals in the restaurant I would definitely recommend this Inn to anyone traveling in southern Vermont."
United States
Kimberley B.
The price is CA $305
CA $528 total
includes taxes & fees
Nov 1 - Nov 2
Luxury King w/balcony, accessible
A modern bedroom with a bed, bedside tables, a dresser, and a fireplace.

12. Deluxe 2xQueen & fireplace

Deluxe 2xQueen & fireplace
Dover
10.0 out of 10, Exceptional, (1 review)
"Beautiful Inn however, the fridge should be lifted off the floor. It’s too low. A small broom and dust pan would be nice to sweep up the dirt that treks in from the dirt parking lot and walk ways. Upgrade full size beds to at least two Queen size beds."
United States
Christina R.
The price is CA $338
CA $562 total
includes taxes & fees
Nov 1 - Nov 2
Deluxe 2xQueen & fireplace
A cozy living room with a fireplace, leather sofas, a wooden coffee table, and a chandelier.

13. Luxury King with balcony

Luxury King with balcony
West Dover
The price is CA $305
CA $528 total
includes taxes & fees
Nov 1 - Nov 2
Luxury King with balcony
A two-story white building with a porch, labeled "Farm Road Estate Historic Inn & Cottages."

14. Deluxe King - 2nd floor in Historic Inn

Deluxe King - 2nd floor in Historic Inn
West Dover
The price is CA $305
CA $528 total
includes taxes & fees
Nov 1 - Nov 2
Deluxe King - 2nd floor in Historic Inn
A bedroom with a large bed, a wooden headboard, a nightstand, and a bench.

15. Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths

Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
West Dover
8.0 out of 10, Very good, (1 review)
"The inn and grounds were wonderful. Great food at the Sawmill. Wonderful area to explore leading to an all around wonderful time."
United States
Craig C.
The price is CA $321
CA $549 total
includes taxes & fees
Nov 1 - Nov 2
Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
A two-story house with a large porch and a pond in front.

16. Deluxe King Suite, Living Room w/sofa bed & fireplace

Deluxe King Suite, Living Room w/sofa bed & fireplace
West Dover
10.0 out of 10, Exceptional, (1 review)
"My husband and I really enjoyed the accommodations. Great location with tons do do nearby. The place was so cozy and inviting. Would definitely stay again"
United States
Megan M.
The price is CA $338
CA $562 total
includes taxes & fees
Nov 1 - Nov 2
Deluxe King Suite, Living Room w/sofa bed & fireplace
A room with two brown leather armchairs, a wooden coffee table with a bowl and a magazine, and a bed with pillows in the background.

17. Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance

Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance
Dover
10.0 out of 10, Exceptional, (2 reviews)
"The place was clean, cozy and comfortable. The whole estate is beautiful."
United States
Mike T.
The price is CA $370
CA $602 total
includes taxes & fees
Nov 1 - Nov 2
Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance
A hotel room with two beds, a desk, a TV, and a window with a city view.

18. Deluxe 2xQueen in Historic Inn

Deluxe 2xQueen in Historic Inn
West Dover
8.0 out of 10, Very good, (1 review)
The price is CA $305
CA $521 total
includes taxes & fees
Nov 1 - Nov 2
Deluxe 2xQueen in Historic Inn
A two-story house with a large porch and a pond in front.

19. Luxury King Suite, Living Room w/sofa bed and jacuzzi tub

Luxury King Suite, Living Room w/sofa bed and jacuzzi tub
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Such a quaint, beautiful Spot. It’s uniqueness, historic feel and common area was very warming. Personnel was very friendly and attentive"
United States
Jessica
The price is CA $321
CA $541 total
includes taxes & fees
Nov 1 - Nov 2
Luxury King Suite, Living Room w/sofa bed and jacuzzi tub
A hotel room with two single beds, a wooden headboard, a small bedside table, and a nightstand with a lamp.

20. Deluxe 2xQueen- 2nd floor in Historic Inn

Deluxe 2xQueen- 2nd floor in Historic Inn
West Dover
10.0 out of 10, Exceptional, (5 reviews)
"Everything was just fantastic! Everyone was friendly and accommodating. Owners were so nice! Property is amazing and a great location to Mount Snow. Can not go wrong with this spot."
United States
Brendan M.
The price is CA $305
CA $528 total
includes taxes & fees
Nov 1 - Nov 2
Deluxe 2xQueen- 2nd floor in Historic Inn
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Latchis Hotel

Latchis Hotel

8/10 Good
"It’s located with restaurants within walking distance. It is well maintained for a historic hotel with probably about 15 steps in the lobby before you get to the elevator. It was noisy some nights due to being in the city and having residents living life. Staff was wonderful. Again location was great to see Buffalo—Niagara is 20 min away, Botanic Garden and Eternal Flame about the same. We enjoyed our stay."
Matthew 1-night trip
Posted 1 day ago
Latchis Hotel

Find out more about Chester

Chester Resorts information

Number of reviews
1,926
Accommodation
28 Resorts
Lowest Price
CA $233
Highest Price
CA $632

Frequently asked questions

What can I expect from a resort vacation in Chester?
You deserve to get away, and a resort is the perfect place to treat yourself to the amenities and services you need for a relaxing trip to Chester. One of the comfortable resort hotels in the surrounding area might be just what you're looking for, whether you want a luxurious suite, shopping possibilities, or fun activities to try.
What's a top resort in Chester?
Here are our top-rated resorts around Chester: Woodstock Inn & Resort - Luxury resort. 25.2 mi (40.5 km) from Chester. Features 4 restaurants, 2 bars, and a golf course. Grand Summit Resort, A Vail Resorts Property - Ski resort, 5-minute walk from Green Mountain National Forest. 25.5 mi (41 km) from Chester. Has ski-in/ski-out access, a full-service spa, and a fitness center. Holiday Inn Club Vacations Mount Ascutney Resort by IHG - 15.4 mi (24.7 km) from Chester. Enjoy the bar, an outdoor tennis court, and restaurant. The Black Bear Lodge at Stratton Mountain Resort - Ski resort, 5-minute walk from Green Mountain National Forest. 18.7 mi (30.1 km) from Chester. Amenities include 10 restaurants, 2 bars, and a sauna. Luxury King w/balcony, accessible - Only a 5-minute walk from Green Mountain National Forest. 25.9 mi (41.7 km) from Chester. Access to a car charging station.
What can I do in Chester?
Travelers enjoy the skiing and other winter sports in Chester, and have good things to say about activities such as shopping. DaVallia Art & Accents and Bonnie's Bundles Dolls are a few of the interesting sights to visit. In the area, other attractions include Vermont Country Store and Lowell Lake State Park.
What's the weather like in Chester?
The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chester are January, March, November, and February, with each month seeing an average of 14 inches of snowfall.
What's the best way to get to and around Chester?
Fly into Springfield, VT (VSF-Hartness State), which is located 6.6 mi (10.7 km) away from the city center. You can also search for flights into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 25.4 mi (40.8 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

Explore a world of travel with Expedia