Best Resorts in Chester

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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

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, (514)
"The Woodstock Inn is beautiful. Nice having access to the Athletic Club and a shuttle."
The price is $373
includes taxes & fees
$339 per night
May 26 - May 27
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, (696)
"Staff was wonderful, easy to get to and convenient location"
The price is $165
includes taxes & fees
$152 per night
May 1 - May 2
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, (193)
"Outdoor pool was great !"
The price is $152
includes taxes & fees
$138 per night
May 4 - May 5
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, (899)
"Great staff and clean!!"
The price is $162
includes taxes & fees
$147 per night
May 29 - May 30
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 $249
includes taxes & fees
$220 per night
May 11 - May 12
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, (12)
"Lovely place to stay, kind staff and great accomodations."
The price is $225
includes taxes & fees
$199 per night
May 11 - May 12
Palmer House Resort - Deluxe King Bed 5
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 $225
includes taxes & fees
$199 per night
May 11 - May 12
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)
The price is $225
includes taxes & fees
$199 per night
May 11 - May 12
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)
"The setting is beautiful. The staff were amazing - kind and attentive. Our room was very dated and in need of updating including the bathrooms. The furniture in the room was an odd collection of pieces that could have come from a yard sale. It was not up to the standard we expected given the cost of the room and the overall resort vibe. "
The price is $1,123
includes taxes & fees
$1,021 per night
May 21 - May 22
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 $361
includes taxes & fees
$331 per night
May 1 - May 2
Deluxe 2xQueen- 2nd floor in Historic Inn
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 $384
includes taxes & fees
$352 per night
May 1 - May 2
Deluxe King Room w/fireplace and separate entrance
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 $225
includes taxes & fees
$199 per night
May 11 - May 12
Palmer House Resort - Deluxe King Bed 1
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 $399
includes taxes & fees
$366 per night
May 1 - May 2
Deluxe King, kitchenette, fireplace
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 $225
includes taxes & fees
$199 per night
May 11 - May 12
Palmer House Resort - Deluxe King Bed 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 $251
includes taxes & fees
$222 per night
May 11 - May 12
Palmer House Resort - Deluxe Two Double Beds 4
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 $399
includes taxes & fees
$366 per night
May 1 - May 2
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 $251
includes taxes & fees
$222 per night
May 11 - May 12
Palmer House Resort - Deluxe Two Double Beds 2
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 $361
includes taxes & fees
$331 per night
May 1 - May 2
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 $251
includes taxes & fees
$222 per night
May 11 - May 12
Palmer House Resort - Deluxe Two Double Beds 5
Deluxe King - 2nd floor in Historic Inn
Aerial view

Deluxe King - 2nd floor in Historic Inn

The price is $375
includes taxes & fees
$344 per night
May 1 - May 2
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
Miscellaneous

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

10.0 out of 10, Exceptional, (23)
"Peaceful vacation"
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
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, (42)
"Very nice place only negative was the sauna did not work"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Outdoor spa tub

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (18)
"This place was absolutely perfect and wonderful. It offered a cozy family getaway to enjoy the southern Vermont scene that we have grown to love so very much. The house and owner are absolutely amazing and we hope to stay here again for our trips back to this area. Highly recommend! "
The price is $644
includes taxes & fees
$574 per night
May 1 - May 2
Your Vermont Mountain Haven Pet Friendly home with Hot 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.

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. If you brought the kids, you can head to DaVallia Art & Accents or Bonnie’s Bundles Dolls for some family fun. In the area, other attractions include Vermont Country Store and Lowell Lake State Park.
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.