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Compare 37 Resorts in Chester with updated reviews, rates, and availability.

Woodstock Inn & Resort
Exterior

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (489)
"The garden level hallways needs a facelift. Room was fine but the corridor carpet had stains and it looked a little dingy. Expected more for a 5 star resort."
The price is AED 1,098
AED 1,370 total
includes taxes & fees
20 Jan - 21 January 2025
Woodstock Inn & Resort
The Black Bear Lodge at Stratton Mountain Resort
Room

The Black Bear Lodge at Stratton Mountain Resort

3.0 star property
7.6 out of 10, Good, (878)
"Very nice, clean property. A tad bit outdated but for a value in the area it’s well worth it. We had an enjoyable stay. "
The price is AED 657
AED 796 total
includes taxes & fees
20 Jan - 21 January 2025
The Black Bear Lodge at Stratton Mountain Resort
Mount Snow Grand Summit Resort
Exterior

Mount Snow Grand Summit Resort

3.0 star property
8.8 out of 10, Excellent, (170)
"👍"
The price is AED 1,029
AED 1,231 total
includes taxes & fees
22 Jan - 23 January 2025
Mount Snow Grand Summit Resort
Holiday Inn Club Vacations Mount Ascutney Resort, an IHG Hotel
Exterior

Holiday Inn Club Vacations Mount Ascutney Resort, an IHG Hotel

3.0 star property
9.0 out of 10, Wonderful, (651)
"Don't have elevator, and no hot breakfast provided "
The price is AED 547
AED 647 total
includes taxes & fees
20 Jan - 21 January 2025
Holiday Inn Club Vacations Mount Ascutney Resort, an IHG Hotel
Equinox Resort Residences
Exterior

Equinox Resort Residences

4.5 star property
8.0 out of 10, Very Good, (2)
"3 room townhouse was great . Check in time is 4 . Wasn’t ready till 430 Also I think carpets in house need to be washed Other than that everything was 10 . "
Equinox Resort Residences
Palmer House Resort - Deluxe King Bed 4
Room

Palmer House Resort - Deluxe King Bed 4

10.0 out of 10, Exceptional, (1)
"Great prices"
The price is AED 584
AED 822 total
includes taxes & fees
5 Jan - 6 January 2025
Palmer House Resort - Deluxe King Bed 4
Palmer House Resort - Deluxe King Bed 2
Room

Palmer House Resort - Deluxe King Bed 2

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...
The price is AED 584
AED 822 total
includes taxes & fees
5 Jan - 6 January 2025
Palmer House Resort - Deluxe King Bed 2
Palmer House Resort - Deluxe King Bed 5
Room

Palmer House Resort - Deluxe King Bed 5

9.2 out of 10, Wonderful, (10)
"It was close to all the downtown restaurants and shops. Cery convenient for us "
The price is AED 584
AED 822 total
includes taxes & fees
5 Jan - 6 January 2025
Palmer House Resort - Deluxe King Bed 5
Palmer House Resort - Deluxe Two Double Beds 4
Interior

Palmer House Resort - Deluxe Two Double Beds 4

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."
The price is AED 657
AED 917 total
includes taxes & fees
5 Jan - 6 January 2025
Palmer House Resort - Deluxe Two Double Beds 4
Palmer House Resort - Deluxe King Bed 1
Room

Palmer House Resort - Deluxe King Bed 1

8.0 out of 10, Very Good, (3)
"It was a beautiful stay. Lovely Accommodations. "
The price is AED 584
AED 822 total
includes taxes & fees
5 Jan - 6 January 2025
Palmer House Resort - Deluxe King Bed 1
Palmer House Resort - Deluxe Two Double Beds 3
Interior

Palmer House Resort - Deluxe Two Double Beds 3

8.0 out of 10, Very Good, (1)
"M"
The price is AED 657
AED 917 total
includes taxes & fees
5 Jan - 6 January 2025
Palmer House Resort - Deluxe Two Double Beds 3
Palmer House Resort - Deluxe King Bed 3
Room

Palmer House Resort - Deluxe King Bed 3

8.8 out of 10, Excellent, (5)
"Efficient and helpful staff. Great location. "
The price is AED 584
AED 822 total
includes taxes & fees
5 Jan - 6 January 2025
Palmer House Resort - Deluxe King Bed 3
Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
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Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance

9.8 out of 10, Exceptional, (7)
"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."
The price is AED 1,052
AED 1,513 total
includes taxes & fees
6 Jan - 7 January 2025
Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
Deluxe King, kitchenette, fireplace
Cider 1 Fireplace

Deluxe King, kitchenette, fireplace

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."
The price is AED 925
AED 1,355 total
includes taxes & fees
6 Jan - 7 January 2025
Deluxe King, kitchenette, fireplace
Deluxe King Room w/fireplace and separate entrance
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Deluxe King Room w/fireplace and separate entrance

10.0 out of 10, Exceptional, (3)
"Everything about stay was wonderful! Anle to check in early which was so nice as we were Soaking wet from rain. Lots Of room. All the amenities. Dinner right there. Comfortable beds. Coffee and tea in room and even a real fireplace. Would love to come back."
The price is AED 883
AED 1,298 total
includes taxes & fees
6 Jan - 7 January 2025
Deluxe King Room w/fireplace and separate entrance
Palmer House Resort - Deluxe Two Double Beds 5
Interior

Palmer House Resort - Deluxe Two Double Beds 5

5.0 out of 10, (2)
"My husband and I were traveling to Vermont for one night stay. We selected this property because it had pretty rooms. Unfortunately that’s not what we received. Checking in our reservation could not be found. Luckily the desk clerk was able to figure out a repeated mistake. She gave us the key to room #60. We expected a beautiful room with 2 beds. What we got was a suite that had badly stained carpet, furniture that needed to be replaced , water stained bathroom walls and dirty bathroom floors....
The price is AED 657
AED 917 total
includes taxes & fees
5 Jan - 6 January 2025
Palmer House Resort - Deluxe Two Double Beds 5
Deluxe 2xQueen- 2nd floor in Historic Inn
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Deluxe 2xQueen- 2nd floor in Historic Inn

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"
The price is AED 798
AED 1,198 total
includes taxes & fees
7 Jan - 8 January 2025
Deluxe 2xQueen- 2nd floor in Historic Inn
Deluxe King - 2nd floor in Historic Inn
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Deluxe King - 2nd floor in Historic Inn

The price is AED 841
AED 1,248 total
includes taxes & fees
6 Jan - 7 January 2025
Deluxe King - 2nd floor in Historic Inn
Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
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Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths

8.0 out of 10, Very Good, (1)
"The inn and grounds were wonderful. Great food at the Sawmill. Wonderful area to explore leading to an all around wonderful time."
The price is AED 841
AED 1,248 total
includes taxes & fees
6 Jan - 7 January 2025
Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
King with Bunk Bed- 2nd floor in Historic Inn
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King with Bunk Bed- 2nd floor in Historic Inn

10.0 out of 10, Exceptional, (2)
"Very well apportioned room. Super clean and comfortable. Restaurant was delicious. Bartender is cool to chat with."
The price is AED 841
AED 1,252 total
includes taxes & fees
5 Jan - 6 January 2025
King with Bunk Bed- 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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Other property types in Chester

Long Trail House at Stratton Mountain Resort
Living room

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very Good, (72)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is AED 1,392
AED 1,731 total
includes taxes & fees
6 Jan - 7 January 2025
Long Trail House at Stratton Mountain Resort
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (40)
"Like property— sad the lift that made it ski and in out was closed due weather conditions "
The price is AED 1,939
AED 2,618 total
includes taxes & fees
10 Jan - 11 January 2025
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
Located in the Okemo Mt. Community, a mile to the base lodge

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location
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.

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. 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. Has 10 restaurants, 2 bars, and a sauna. Mount Snow Grand Summit Resort - 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. Holiday Inn Club Vacations Mount Ascutney Resort, an IHG Hotel - 15.4 mi (24.7 km) from Chester. Amenities include a seasonal outdoor pool, a bar, and an indoor pool. 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. Vermont Country Store offers fun for the whole family, while Okemo Mountain Resort is one of the most popular places to visit nearby. A few other attractions you may want to see are DaVallia Art & Accents and Bonnie’s Bundles Dolls.
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.