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Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Compare 35 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, (501)
"Great resort, beautiful property-only issue was room was cold - aside from that, loved the stay "
The price is AED 1,098
AED 1,370 total
includes taxes & fees
2 Mar - 3 Mar
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, (892)
"The place was very nice but a little dated"
The price is AED 657
AED 796 total
includes taxes & fees
6 Mar - 7 Mar
The Black Bear Lodge at Stratton Mountain Resort
Holiday Inn Club Vacations Mount Ascutney Resort
Exterior

Holiday Inn Club Vacations Mount Ascutney Resort

3.0 star property
9.0 out of 10, Wonderful, (672)
"Great stay and friendly staff, rooms are clean and spacious! Will definitely come back! "
The price is AED 474
AED 567 total
includes taxes & fees
24 Feb - 25 Feb
Holiday Inn Club Vacations Mount Ascutney Resort
Mount Snow Grand Summit Resort
Exterior

Mount Snow Grand Summit Resort

3.0 star property
8.8 out of 10, Excellent, (180)
"Older, air drying in the locker rooms odd . Moisture. "
The price is AED 980
AED 1,173 total
includes taxes & fees
18 Mar - 19 Mar
Mount Snow Grand Summit Resort
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 826 total
includes taxes & fees
23 Feb - 24 Feb
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 826 total
includes taxes & fees
23 Feb - 24 Feb
Palmer House Resort - Deluxe King Bed 2
Palmer House Resort - Deluxe King Bed 5
Room

Palmer House Resort - Deluxe King Bed 5

9.4 out of 10, Exceptional, (11)
"Clean, spacious suites, located convenient to town and ski areas.Bathroom was gigantic and included a Jacuzzi tub and a second vanity for my daughter and her friend.Michael was a warm and gracious desk host!"
The price is AED 584
AED 826 total
includes taxes & fees
23 Feb - 24 Feb
Palmer House Resort - Deluxe King Bed 5
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 826 total
includes taxes & fees
23 Feb - 24 Feb
Palmer House Resort - Deluxe King Bed 3
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 826 total
includes taxes & fees
23 Feb - 24 Feb
Palmer House Resort - Deluxe King Bed 1
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 921 total
includes taxes & fees
23 Feb - 24 Feb
Palmer House Resort - Deluxe Two Double Beds 4
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 921 total
includes taxes & fees
23 Feb - 24 Feb
Palmer House Resort - Deluxe Two Double Beds 3
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 418
AED 743 total
includes taxes & fees
17 Mar - 18 Mar
Deluxe 2xQueen- 2nd floor in Historic Inn
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 672
AED 1,051 total
includes taxes & fees
17 Mar - 18 Mar
Luxury King Cottage, 2 twin beds in loft, fireplace, private 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 921 total
includes taxes & fees
23 Feb - 24 Feb
Palmer House Resort - Deluxe Two Double Beds 5
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, (4)
"We thoroughly enjoyed our one-night stay. Our room was cozy and all the staff were wonderful."
The price is AED 376
AED 689 total
includes taxes & fees
17 Mar - 18 Mar
Deluxe King Room w/fireplace and separate 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 376
AED 689 total
includes taxes & fees
17 Mar - 18 Mar
Deluxe King, kitchenette, fireplace
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 418
AED 743 total
includes taxes & fees
17 Mar - 18 Mar
King with Bunk Bed- 2nd floor in Historic Inn
Palmer House Resort - Deluxe Two Double Beds 2
Interior

Palmer House Resort - Deluxe Two Double Beds 2

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...
The price is AED 657
AED 921 total
includes taxes & fees
23 Feb - 24 Feb
Palmer House Resort - Deluxe Two Double Beds 2
Deluxe King - 2nd floor in Historic Inn
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Deluxe King - 2nd floor in Historic Inn

The price is AED 334
AED 634 total
includes taxes & fees
17 Mar - 18 Mar
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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Other property types in Chester

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Summer Quiet...

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

10.0 out of 10, Exceptional, (22)
"Loved being tucked away in the wilderness. Owners were very responsive. "
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
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 1,524
AED 1,894 total
includes taxes & fees
3 Mar - 4 Mar
Long Trail House at Stratton Mountain Resort
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Secluded covered entry

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (206)
"Perfect get away. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
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. Holiday Inn Club Vacations Mount Ascutney Resort - 15.4 mi (24.7 km) from Chester. Enjoy the seasonal outdoor pool, bar, and an indoor pool. 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. 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. 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.