Best Resorts in Chester

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Resorts in Chester

Indoor spa tub
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, (931)
"Great place for the price "
United States
Karen
$151 nightly
The price is $166
Nov 9 - Nov 10
Total with taxes and fees
The Black Bear Lodge at Stratton Mountain Resort
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, (771)
"Strongly recommend and will go back again!"
Canada
Craig
$142 nightly
The price is $154
Dec 8 - Dec 9
Total with taxes and fees
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Front of property
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3.0 star property
West Dover
8.8 out of 10, Excellent, (242)
"Free shuttle service to Dover is wonderful! Staff were friendly and helpful."
United States
Chris
$161 nightly
The price is $177
Nov 10 - Nov 11
Total with taxes and fees
Mount Snow Grand Summit Resort
Terrace/patio
Palmer House Resort - Deluxe King Bed 2

Palmer House Resort - Deluxe King Bed 2

Manchester Center,
8.0 out of 10, Very Good, (2)
"My wife and I selected Palmer House based on the photos on VRBO. Upon driving the property towards our room we suddenly realized things looked different. Upon entering the room we noticed a distinct smell. The bathroom shown online looks very nice and updated with a beautiful shower, white cabinets and looked very modern. Ours was nothing like that. We had a tan handicap tub, urine stained tiles, a counter and sink that looked very old, and old brown cabinets. Needless to say we were...
United States
Mark A.
$199 nightly
The price is $225
Nov 16 - Nov 17
Total with taxes and fees
Palmer House Resort - Deluxe King Bed 2
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 star property
Woodstock
9.2 out of 10, Wonderful, (546)
"I’ve traveled a lot around the world and this hotel has to be in my top 3 ever. Especially beautiful in autumn"
United States
Kevin
$369 nightly
The price is $406
Nov 30 - Dec 1
Total with taxes and fees
Woodstock Inn & Resort
Exterior
Deluxe 2xQueen- 2nd floor in Historic Inn

Deluxe 2xQueen- 2nd floor in Historic Inn

West Dover
10.0 out of 10, Exceptional, (5)
"Gorgeous property in a wonderful area. It was IMMACULATELY clean and cozy. We loved our stay and had plenty of recommendations for things to do nearby. The restaurant was lovely and again so cute and cozy. The only negative I can say is that the bar was way overpriced. We would be happy to stay again"
United States
Ciara O.
$319 nightly
The price is $347
Nov 9 - Nov 10
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)
"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.
$367 nightly
The price is $400
Nov 10 - Nov 11
Total with taxes and fees
Deluxe King, kitchenette, fireplace
Exterior
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)
"We thoroughly enjoyed our one-night stay. Our room was cozy and all the staff were wonderful."
United States
Charles B.
$372 nightly
The price is $405
Nov 9 - Nov 10
Total with taxes and fees
Deluxe King Room w/fireplace and separate entrance
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)
"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
$393 nightly
The price is $428
Nov 9 - Nov 10
Total with taxes and fees
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
Terrace/patio
Palmer House Resort - Deluxe King Bed 5

Palmer House Resort - Deluxe King Bed 5

Manchester Center, , VT, US
9.4 out of 10, Exceptional, (12)
"Excellent hospitality, friendly staff, quality stay."
United States
Nicolas S.
$199 nightly
The price is $225
Nov 16 - Nov 17
Total with taxes and fees
Palmer House Resort - Deluxe King Bed 5
Terrace/patio
Palmer House Resort - Deluxe King Bed 3

Palmer House Resort - Deluxe King Bed 3

Manchester Center,
8.8 out of 10, Excellent, (5)
"Efficient and helpful staff. Great location. "
United States
Kevin
$199 nightly
The price is $225
Nov 16 - Nov 17
Total with taxes and fees
Palmer House Resort - Deluxe King Bed 3
Terrace/patio
Palmer House Resort - Deluxe King Bed 1

Palmer House Resort - Deluxe King Bed 1

Manchester Center,
8.0 out of 10, Very Good, (4)
"When i called to tell them i forgot my pillow. They sent it to me immediately and did not charge me. "
United States
R. Sherry
$199 nightly
The price is $225
Nov 16 - Nov 17
Total with taxes and fees
Palmer House Resort - Deluxe King Bed 1
Terrace/patio
Palmer House Resort - Deluxe Two Double Beds 2

Palmer House Resort - Deluxe Two Double Beds 2

Manchester Center,
8.0 out of 10, Very Good, (1)
"I will start with the negatives and close with the positives. I wasn't convinced the towels were clean and there was literally only one each for us, seemed there was no attention to detail with cleaning (lots of hair and dust in corners in bathroom, 1/2 used sugar packet in the selection at the coffeemaker, bed skirt dragging on the floor, etc.), breakfast was lame, but I get it, because it's covid. For the positives, location was AWESOME, the room was super spacious with updated climate...
United States
Bridget N.
$222 nightly
The price is $251
Nov 16 - Nov 17
Total with taxes and fees
Palmer House Resort - Deluxe Two Double Beds 2
Terrace/patio
Palmer House Resort - Deluxe Two Double Beds 4

Palmer House Resort - Deluxe Two Double Beds 4

Manchester Center,
8.0 out of 10, Very Good, (6)
"We enjoyed our stay at the Palmer House in Manchester Center, VT. The staff was friendly and accommodating. Especially enjoyed sitting by the fire pit on a chilly evening."
United States
Mark S.
$222 nightly
The price is $251
Nov 16 - Nov 17
Total with taxes and fees
Palmer House Resort - Deluxe Two Double Beds 4
Terrace/patio
Palmer House Resort - Deluxe King Bed 4

Palmer House Resort - Deluxe King Bed 4

Manchester Center,
6.0 out of 10, (2)
"Great prices"
United States
Peter T.
$199 nightly
The price is $225
Nov 16 - Nov 17
Total with taxes and fees
Palmer House Resort - Deluxe King Bed 4
Terrace/patio
Palmer House Resort - Deluxe Two Double Beds 3

Palmer House Resort - Deluxe Two Double Beds 3

Manchester Center,
8.0 out of 10, Very Good, (1)
"M"
United States
Theresa
$221 nightly
The price is $250
Nov 16 - Nov 17
Total with taxes and fees
Palmer House Resort - Deluxe Two Double Beds 3
Exterior
Luxury King w/balcony, accessible

Luxury King w/balcony, accessible

West Dover
10.0 out of 10, Exceptional, (2)
"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.
$341 nightly
The price is $371
Nov 9 - Nov 10
Total with taxes and fees
Luxury King w/balcony, accessible
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)
"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.
$393 nightly
The price is $428
Nov 10 - Nov 11
Total with taxes and fees
Deluxe King Suite, Living Room w/sofa bed & fireplace
Interior
Luxury King with balcony

Luxury King with balcony

West Dover
$358 nightly
The price is $391
Nov 9 - Nov 10
Total with taxes and fees
Luxury King with balcony
Exterior
Deluxe King- 2nd floor in Historic Inn

Deluxe King- 2nd floor in Historic Inn

West Dover
$332 nightly
The price is $362
Nov 9 - Nov 10
Total with taxes and fees
Deluxe King- 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.
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Top Chester Hotel Reviews

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

10/10 Excellent
"Nice clean room and friendly staff. I was there off season (early November) so some restaurants weren’t open but there were still plenty of options. "
Andrew 1-night trip
Posted 2 days ago
Pointe at Castle Hill Resort

Find out more about Chester

Chester Resorts information

Number of reviews
2,505
Accommodation
41 Resorts
Lowest Price
$154
Highest Price
$428

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. Holiday Inn Club Vacations Mount Ascutney Resort by IHG - 15.4 mi (24.7 km) from Chester. Has a seasonal outdoor pool, a bar, and an indoor pool. 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. Enjoy the 10 restaurants, 2 bars, and sauna. Mount Snow Grand Summit Resort - Ski resort, 5-minute walk from Mount Snow. 25.5 mi (41 km) from Chester. Amenities include ski-in/ski-out access, a full-service spa, and a fitness center. Equinox Resort Residences - Luxury resort. 25 mi (40.3 km) from Chester. Access to 4 restaurants, 2 bars, and a golf course.
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 Grafton Historical Society and Vermont Country Store.
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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