Best Resorts in Chester

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Our top choices for Chester resorts

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, (830 reviews)
"The room was clean. Plenty of seats for everyone. The kitchen has dishes, utensils, bowls, pots, casserole dish, knives. Beds are comfortable. I will definitely return for a stay and recommend to others. "
United States
Kimberly
$169 nightly
The price is $184
May 7 - May 8
Total with taxes and fees
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

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, (991 reviews)
"Amazing hotel"
United States
Luis
$149 nightly
The price is $164
May 10 - May 11
Total with taxes and fees
The Black Bear Lodge at Stratton Mountain Resort

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, (268 reviews)
"Great place to stay for ski trip"
United States
carlos
$143 nightly
The price is $157
May 11 - May 12
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 reviews)
"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.
$207 nightly
The price is $234
May 13 - May 14
Total with taxes and fees
Palmer House Resort - Deluxe King Bed 2

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.
$240 nightly
The price is $260
May 7 - May 8
Total with taxes and fees
Deluxe 2xQueen- 2nd floor in Historic Inn

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
$293 nightly
The price is $318
May 7 - May 8
Total with taxes and fees
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (575 reviews)
"Always an Amazing time when we stay here. Property well maintained, staff is super friendly and the food here is above and beyond. Did I mention I got married here 👍👍"
United States
Daniele
$359 nightly
The price is $395
May 25 - May 26
Total with taxes and fees
Woodstock Inn & Resort

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.
$262 nightly
The price is $284
May 7 - May 8
Total with taxes and fees
Deluxe King, kitchenette, 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 reviews)
"We thoroughly enjoyed our one-night stay. Our room was cozy and all the staff were wonderful."
United States
Charles B.
$266 nightly
The price is $288
May 7 - May 8
Total with taxes and fees
Deluxe King Room w/fireplace and separate entrance

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 reviews)
"Lovely place to stay, kind staff and great accomodations."
United States
Nicolas S.
$207 nightly
The price is $234
May 13 - May 14
Total with taxes and fees
Palmer House Resort - Deluxe King Bed 5

Palmer House Resort - Deluxe King Bed 1

Palmer House Resort - Deluxe King Bed 1
Manchester Center,
8.0 out of 10, Very Good, (4 reviews)
"It was a beautiful stay. Lovely Accommodations. "
United States
Linda P.
$210 nightly
The price is $237
May 13 - May 14
Total with taxes and fees
Palmer House Resort - Deluxe King Bed 1

Palmer House Resort - Deluxe King Bed 3

Palmer House Resort - Deluxe King Bed 3
Manchester Center,
8.8 out of 10, Excellent, (5 reviews)
"Efficient and helpful staff. Great location. "
United States
Kevin
$207 nightly
The price is $234
May 13 - May 14
Total with taxes and fees
Palmer House Resort - Deluxe King Bed 3

Luxury King with balcony

Luxury King with balcony
West Dover
$240 nightly
The price is $260
May 7 - May 8
Total with taxes and fees
Luxury King with balcony

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 reviews)
"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
May 13 - May 14
Total with taxes and fees
Palmer House Resort - Deluxe Two Double Beds 4

Deluxe 2xQueen in Historic Inn

Deluxe 2xQueen in Historic Inn
West Dover
8.0 out of 10, Very Good, (1 review)
$237 nightly
The price is $256
May 7 - May 8
Total with taxes and fees
Deluxe 2xQueen in Historic Inn

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 review)
"M"
United States
Theresa
$230 nightly
The price is $260
May 13 - May 14
Total with taxes and fees
Palmer House Resort - Deluxe Two Double Beds 3

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.
$240 nightly
The price is $260
May 7 - May 8
Total with taxes and fees
King with Bunk Bed- 2nd floor in Historic Inn

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.
$240 nightly
The price is $260
May 7 - May 8
Total with taxes and fees
Luxury King w/balcony, accessible

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 review)
"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
May 13 - May 14
Total with taxes and fees
Palmer House Resort - Deluxe Two Double Beds 2

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
$237 nightly
The price is $256
May 7 - May 8
Total with taxes and fees
Luxury King Suite, Living Room w/sofa bed and jacuzzi tub
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

Find out more about Chester

Chester Resorts information

Number of reviews
1,717
Accommodation
40 Resorts
Lowest Price
$157
Highest Price
$395

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 bar, an outdoor tennis court, and a restaurant. Grand Summit Resort, A Vail Resorts Property - Ski resort, 5-minute walk from Mount Snow. 25.5 mi (41 km) from Chester. Enjoy the ski-in/ski-out access, spa, and fitness center. 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. Palmer House Resort - Deluxe King Bed 5 - Golf resort. 23.5 mi (37.9 km) from Chester. Access to a garden, free breakfast, and an indoor pool.
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 North Springfield Lake Recreation Area.
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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