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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

Compare 41 Resorts in Chester with updated reviews, rates, and availability.

Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (504)
"The Woodstock Inn & Resort is the quintessential New England inn. Walk in the lobby and you are greeted by a large warm fire. The staff at all levels were gracious and helpful. The room was large, well decorated and extremely comfortable. Great location to walk downtown even with single digit temperatures. The shops were expensive but worth browsing & buying. "
The price is AED 1,098
AED 1,370 total
includes taxes & fees
23 Mar - 24 Mar
Woodstock Inn & Resort
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Exterior

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3.0 star property
9.0 out of 10, Wonderful, (678)
"Great accommodations for families and small groups. Units well stocked and clean. Best value for lodging in the area by far! "
The price is AED 437
AED 526 total
includes taxes & fees
24 Mar - 25 Mar
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Mount Snow Grand Summit Resort
Exterior

Mount Snow Grand Summit Resort

3.0 star property
8.6 out of 10, Excellent, (189)
"Ski in/ Ski out"
The price is AED 547
AED 655 total
includes taxes & fees
14 Apr - 15 Apr
Mount Snow Grand Summit Resort
The Black Bear Lodge at Stratton Mountain Resort
Indoor spa tub

The Black Bear Lodge at Stratton Mountain Resort

3.0 star property
7.6 out of 10, Good, (896)
"appreciated the breakfast and in hotel restaurant."
The price is AED 490
AED 593 total
includes taxes & fees
16 Apr - 17 Apr
The Black Bear Lodge at Stratton Mountain Resort
Palmer House Resort - Deluxe Two Double Beds 3
Terrace/patio

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
30 Mar - 31 Mar
Palmer House Resort - Deluxe Two Double Beds 3
Palmer House Resort - Deluxe King Bed 5
Terrace/patio

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
30 Mar - 31 Mar
Palmer House Resort - Deluxe King Bed 5
Palmer House Resort - Deluxe King Bed 1
Terrace/patio

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
30 Mar - 31 Mar
Palmer House Resort - Deluxe King Bed 1
Palmer House Resort - Deluxe King Bed 3
Terrace/patio

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
30 Mar - 31 Mar
Palmer House Resort - Deluxe King Bed 3
Palmer House Resort - Deluxe King Bed 4
Terrace/patio

Palmer House Resort - Deluxe King Bed 4

6.0 out of 10, (2)
"Great prices"
The price is AED 584
AED 826 total
includes taxes & fees
30 Mar - 31 Mar
Palmer House Resort - Deluxe King Bed 4
Equinox Resort Residences
Indoor pool, open 8:00 AM to 6:00 PM, sun loungers

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 . "
The price is AED 2,334
AED 3,572 total
includes taxes & fees
13 Apr - 14 Apr
Equinox Resort Residences
Deluxe 2xQueen- 2nd floor in Historic Inn
1 bedroom, iron/ironing board, WiFi

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 1,220 total
includes taxes & fees
25 Mar - 26 Mar
Deluxe 2xQueen- 2nd floor in Historic Inn
Palmer House Resort - Deluxe King Bed 2
Terrace/patio

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
30 Mar - 31 Mar
Palmer House Resort - Deluxe King Bed 2
Deluxe King Room w/fireplace and separate entrance
Aerial view

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 756
AED 1,161 total
includes taxes & fees
23 Mar - 24 Mar
Deluxe King Room w/fireplace and separate entrance
Deluxe King, kitchenette, fireplace
1 bedroom, iron/ironing board, WiFi, bed sheets

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 756
AED 1,144 total
includes taxes & fees
24 Mar - 25 Mar
Deluxe King, kitchenette, fireplace
Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
Aerial view

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 1,532 total
includes taxes & fees
23 Mar - 24 Mar
Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
Palmer House Resort - Deluxe Two Double Beds 2
Terrace/patio

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
30 Mar - 31 Mar
Palmer House Resort - Deluxe Two Double Beds 2
Palmer House Resort - Deluxe Two Double Beds 4
Terrace/patio

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
30 Mar - 31 Mar
Palmer House Resort - Deluxe Two Double Beds 4
Deluxe King - 2nd floor in Historic Inn
Aerial view

Deluxe King - 2nd floor in Historic Inn

The price is AED 714
AED 1,114 total
includes taxes & fees
30 Mar - 31 Mar
Deluxe King - 2nd floor in Historic Inn
King with Bunk Bed- 2nd floor in Historic Inn
A heated pool

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 798
AED 1,215 total
includes taxes & fees
23 Mar - 24 Mar
King with Bunk Bed- 2nd floor in Historic Inn
Palmer House Resort - Deluxe Two Double Beds 5
Terrace/patio

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
30 Mar - 31 Mar
Palmer House Resort - Deluxe Two Double Beds 5
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
Miscellaneous

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

10.0 out of 10, Exceptional, (23)
"This lovingly built off-grid glamping cabin is drenched with sun! It’s absolutely gorgeous! The kids enjoyed pumping their own water and sledding down the front hill. Paris is an excellent hostess- she answered all our questions very promptly & thoroughly. We cant wait to come back! Thank you!!!"
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is AED 1,267
AED 1,575 total
includes taxes & fees
13 Apr - 14 Apr
Long Trail House at Stratton Mountain Resort
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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. Holiday Inn Club Vacations Mount Ascutney Resort by IHG - 15.4 mi (24.7 km) from Chester. Has a seasonal outdoor pool, a 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. 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. 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.