Search Resort Hotels in Chester from CA $199

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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, (995 reviews)
"Rooms were clean, some wear noticeable. Staff very friendly and helpful."
United States
Paul
The price is CA $165
CA $199 total
includes taxes & fees
May 24 - May 25
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, (833 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
The price is CA $192
CA $232 total
includes taxes & fees
May 25 - May 26
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

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
The price is CA $181
CA $217 total
includes taxes & fees
May 26 - May 27
Grand Summit Resort, A Vail Resorts Property

Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (580 reviews)
"Perfect staff and excellent accommodations. 30th anniversary celebration at a perfect hotel."
United States
Christopher
The price is CA $897
CA $1,047 total
includes taxes & fees
May 28 - May 29
Woodstock Inn & Resort

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.
The price is CA $233
CA $324 total
includes taxes & fees
May 31 - Jun 1
Palmer House Resort - Deluxe King Bed 2

Deluxe King- 2nd floor in Historic Inn

Deluxe King- 2nd floor in Historic Inn
West Dover
The price is CA $204
CA $334 total
includes taxes & fees
May 26 - May 27
Deluxe King- 2nd floor in Historic Inn

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 $331
CA $552 total
includes taxes & fees
May 26 - May 27
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.
The price is CA $331
CA $552 total
includes taxes & fees
May 26 - May 27
Deluxe King Room w/fireplace and separate entrance

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 $363
CA $592 total
includes taxes & fees
May 26 - May 27
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace

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.
The price is CA $233
CA $324 total
includes taxes & fees
May 31 - Jun 1
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.
The price is CA $233
CA $324 total
includes taxes & fees
May 31 - Jun 1
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
The price is CA $233
CA $324 total
includes taxes & fees
May 31 - Jun 1
Palmer House Resort - Deluxe King Bed 3

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.
The price is CA $260
CA $360 total
includes taxes & fees
May 31 - Jun 1
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 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.
The price is CA $260
CA $360 total
includes taxes & fees
May 31 - Jun 1
Palmer House Resort - Deluxe Two Double Beds 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 review)
"M"
United States
Theresa
The price is CA $260
CA $360 total
includes taxes & fees
May 31 - Jun 1
Palmer House Resort - Deluxe Two Double Beds 3

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 $315
CA $532 total
includes taxes & fees
May 26 - May 27
Deluxe 2xQueen- 2nd floor in Historic Inn

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.
The price is CA $331
CA $552 total
includes taxes & fees
May 26 - May 27
Deluxe King, Living Room w/sofa bed & fireplace

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 $331
CA $552 total
includes taxes & fees
May 26 - May 27
Deluxe King Suite, Living Room w/sofa bed & fireplace

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 $331
CA $552 total
includes taxes & fees
May 26 - May 27
Luxury King w/balcony, accessible

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 $331
CA $552 total
includes taxes & fees
May 26 - May 27
Deluxe King Room w/pull-out love seat and fireplace
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
2,723
Accommodation
40 Resorts
Lowest Price
CA $199
Highest Price
CA $1,047

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. The Equinox Golf Resort And Spa - 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 Vermont Country Store and The Nature Museum.
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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