Best Resorts in Chester

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Our top choices for Chester resorts

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, (944)
"Place definitely needs some updating but it was clean and the staff was great!"
United States
Jacqueline
$180 nightly
The price is $198
Jan 14 - Jan 15, 2026
Total with taxes and fees
The Black Bear Lodge at Stratton Mountain Resort

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, (780)
"Clean room, very nice staff, everything was excellent! "
United States
Karen
$144 nightly
The price is $157
Jan 5 - Jan 6, 2026
Total with taxes and fees
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.2 out of 10, Wonderful, (558)
"Luxurious and friendly resort! Loved it"
United States
Elizabeth
$359 nightly
The price is $395
Jan 19 - Jan 20, 2026
Total with taxes and fees
Woodstock Inn & Resort

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property
3.0 star property
West Dover
8.8 out of 10, Excellent, (244)
"Great place to stay!"
United States
Sonia
$333 nightly
The price is $366
Dec 24 - Dec 25
Total with taxes and fees
Grand Summit Resort, A Vail Resorts Property

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.
$211 nightly
The price is $238
Jan 4 - Jan 5, 2026
Total with taxes and fees
Palmer House Resort - Deluxe King Bed 2

Deluxe 2xQueen in Historic Inn

Deluxe 2xQueen in Historic Inn
West Dover
$469 nightly
The price is $512
Jan 6 - Jan 7, 2026
Total with taxes and fees
Deluxe 2xQueen in Historic Inn

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)
"Lovely place to stay, kind staff and great accomodations."
United States
Nicolas S.
$208 nightly
The price is $235
Jan 4 - Jan 5, 2026
Total with taxes and fees
Palmer House Resort - Deluxe King Bed 5

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.
$507 nightly
The price is $555
Jan 6 - Jan 7, 2026
Total with taxes and fees
Deluxe King, kitchenette, fireplace

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
$560 nightly
The price is $613
Jan 6 - Jan 7, 2026
Total with taxes and fees
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace

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.
$501 nightly
The price is $548
Jan 6 - Jan 7, 2026
Total with taxes and fees
Deluxe King Room w/fireplace and separate entrance

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
$208 nightly
The price is $235
Jan 4 - Jan 5, 2026
Total with taxes and fees
Palmer House Resort - Deluxe King Bed 3

Palmer House Resort - Deluxe King Bed 1

Palmer House Resort - Deluxe King Bed 1
Manchester Center,
8.0 out of 10, Very Good, (4)
"It was a beautiful stay. Lovely Accommodations. "
United States
Linda P.
$211 nightly
The price is $238
Jan 4 - Jan 5, 2026
Total with taxes and fees
Palmer House Resort - Deluxe King Bed 1

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.
$230 nightly
The price is $260
Jan 4 - Jan 5, 2026
Total with taxes and fees
Palmer House Resort - Deluxe Two Double Beds 2

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.
$233 nightly
The price is $263
Jan 4 - Jan 5, 2026
Total with taxes and fees
Palmer House Resort - Deluxe Two Double Beds 4

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.
$211 nightly
The price is $238
Jan 4 - Jan 5, 2026
Total with taxes and fees
Palmer House Resort - Deluxe King Bed 4

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
$230 nightly
The price is $260
Jan 4 - Jan 5, 2026
Total with taxes and fees
Palmer House Resort - Deluxe Two Double Beds 3

Luxury King with balcony

Luxury King with balcony
West Dover
$488 nightly
The price is $534
Jan 6 - Jan 7, 2026
Total with taxes and fees
Luxury King with balcony

Deluxe 2xQueen- 2nd floor in Historic Inn

Deluxe 2xQueen- 2nd floor in Historic Inn
West Dover
10.0 out of 10, Exceptional, (5)
"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.
$476 nightly
The price is $520
Jan 6 - Jan 7, 2026
Total with taxes and fees
Deluxe 2xQueen- 2nd floor in Historic Inn

Deluxe King- 2nd floor in Historic Inn

Deluxe King- 2nd floor in Historic Inn
West Dover
$476 nightly
The price is $520
Jan 6 - Jan 7, 2026
Total with taxes and fees
Deluxe King- 2nd floor in Historic Inn

Deluxe King - 2nd floor in Historic Inn

Deluxe King - 2nd floor in Historic Inn
West Dover
$476 nightly
The price is $520
Jan 6 - Jan 7, 2026
Total with taxes and fees
Deluxe King - 2nd floor in Historic Inn
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Top Chester Hotel Reviews

Find out more about Chester

Chester Resorts information

Number of reviews
2,542
Accommodation
41 Resorts
Lowest Price
$157
Highest Price
$613

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 seasonal outdoor pool, 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. Amenities include 10 restaurants, 2 bars, and a sauna. 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. Bonnie's Bundles Dolls offers fun for the whole family, while Stratton Mountain Resort is one of the most popular places to visit nearby. In the area, other attractions include DaVallia Art & Accents 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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