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Best Resorts in Chester

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Check prices for these dates

Next weekend
Jul 10 - Jul 12
In two weeks
Jul 17 - Jul 19
In one month
Jul 31 - Aug 2
In two months
Aug 28 - Aug 30

Our top choices for Chester resorts

Exterior

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, (850 reviews)
"Location of resort is beautiful!! We were not there very long or at resort for many hours but was well kept, beautiful area. Clean and well stocked. Would definitely return."
United States
Carol
$184 nightly
The price is $201
Jun 30 - Jul 1
Total with taxes and fees
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Lobby

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (589 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."
United States
Christopher
$479 nightly
The price is $527
Jun 30 - Jul 1
Total with taxes and fees
Woodstock Inn & Resort
Interior

Deluxe King Room w/fireplace and separate entrance

Deluxe King Room w/fireplace and separate entrance
West Dover
10.0 out of 10, Exceptional, (4 reviews)
"We thoroughly enjoyed our one-night stay. Our room was cozy and all the staff were wonderful."
United States
Charles B.
$370 nightly
The price is $403
Jun 30 - Jul 1
Total with taxes and fees
Deluxe King Room w/fireplace and separate entrance
1 bedroom, iron/ironing board, WiFi

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.
$370 nightly
The price is $403
Jun 30 - Jul 1
Total with taxes and fees
Deluxe 2xQueen- 2nd floor in Historic Inn
Exterior

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.
$434 nightly
The price is $474
Jun 30 - Jul 1
Total with taxes and fees
Deluxe King, kitchenette, fireplace
Exterior

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
$434 nightly
The price is $474
Jun 30 - Jul 1
Total with taxes and fees
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
1 bedroom, iron/ironing board, WiFi

Deluxe 2xQueen in Historic Inn

Deluxe 2xQueen in Historic Inn
West Dover
8.0 out of 10, Very Good, (1 review)
$372 nightly
The price is $405
Jul 1 - Jul 2
Total with taxes and fees
Deluxe 2xQueen in Historic Inn
Exterior

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.
$408 nightly
The price is $446
Jun 30 - Jul 1
Total with taxes and fees
Luxury King w/balcony, accessible
1 bedroom, iron/ironing board, WiFi

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.
$434 nightly
The price is $474
Jun 30 - Jul 1
Total with taxes and fees
Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance
Dining

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.
$408 nightly
The price is $446
Jun 30 - Jul 1
Total with taxes and fees
Deluxe King Room w/pull-out love seat and fireplace
1 bedroom, iron/ironing board, WiFi

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.
$370 nightly
The price is $403
Jun 30 - Jul 1
Total with taxes and fees
Deluxe 2xQueen & fireplace
Exterior

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.
$408 nightly
The price is $446
Jun 30 - Jul 1
Total with taxes and fees
King with Bunk Bed- 2nd floor in Historic Inn
Exterior

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
$408 nightly
The price is $446
Jun 30 - Jul 1
Total with taxes and fees
Luxury King Suite, Living Room w/sofa bed and jacuzzi tub
Exterior

Deluxe King, Living Room w/sofa bed & fireplace

Deluxe King, Living Room w/sofa bed & fireplace
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Had a really nice time - the place was lovely. They had some on property activities and were very close to the mountain. We had a great time and would definitely stay here again if back in the area!"
United States
Taylor G.
$434 nightly
The price is $474
Jun 30 - Jul 1
Total with taxes and fees
Deluxe King, Living Room w/sofa bed & fireplace
Exterior

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.
$434 nightly
The price is $474
Jun 30 - Jul 1
Total with taxes and fees
Deluxe King Suite, Living Room w/sofa bed & fireplace
Interior

Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance

Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
Dover
9.8 out of 10, Exceptional, (7 reviews)
"My husband and I stayed here so we could ride Mt Snow for a few days. The place is wonderful! All staff is incredibly helpful and friendly, the food and cocktails in their restaurant are phenomenal, the landscape and accommodation are beautiful. We will definitely be back."
United States
Sydney W.
$486 nightly
The price is $532
Jun 30 - Jul 1
Total with taxes and fees
Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
Interior

Deluxe Queen Suite with pull-out love seat, private entrance

Deluxe Queen Suite with pull-out love seat, private entrance
Dover
$370 nightly
The price is $403
Jun 30 - Jul 1
Total with taxes and fees
Deluxe Queen Suite with pull-out love seat, private entrance
1 bedroom, iron/ironing board, WiFi

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.
$411 nightly
The price is $449
Jul 1 - Jul 2
Total with taxes and fees
Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
Exterior

Deluxe King - 2nd floor in Historic Inn

Deluxe King - 2nd floor in Historic Inn
West Dover
$408 nightly
The price is $446
Jun 30 - Jul 1
Total with taxes and fees
Deluxe King - 2nd floor in Historic Inn
Interior

Luxury King with balcony

Luxury King with balcony
West Dover
$408 nightly
The price is $446
Jun 30 - Jul 1
Total with taxes and fees
Luxury King with balcony
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.
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Top Chester Hotel Reviews

The Putney Inn

The Putney Inn

10/10 Excellent
"The location is ideal for pursuing a huge variety of interests, and the rooms have all of the expected amenities and are clean and comfortable."
Russell 2-night trip
Posted 5 hours ago
The Putney Inn

Find out more about Chester

Chester Resorts information

Number of reviews
1,482
Accommodation
40 Resorts
Lowest Price
$201
Highest Price
$532

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 Mount Snow. 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 Equinox Golf Resort And Spa - Luxury resort. 25 mi (40.3 km) from Chester. Amenities include 4 restaurants, 2 bars, and a golf course. The Black Bear Lodge at Stratton Mountain Resort - Ski resort, 5-minute walk from Stratton Mountain Resort. 18.7 mi (30.1 km) from Chester. Access to 10 restaurants, 2 bars, and a sauna.
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. If you brought the kids, you can head to DaVallia Art & Accents or Bonnie's Bundles Dolls for some family fun. 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.

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