Search Resorts in Chester

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
7 Saf. - 9 Saf.
In two weeks
14 Saf. - 16 Saf.
In one month
28 Saf. - 2 Rab. I
In two months
28 Rab. I - 30 Rab. I

Compare 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, (500)
"Great trip! "
The price is SAR 1,159
SAR 1,440 total
includes taxes & fees
23 Feb - 24 Feb
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, (890)
"The place was very nice but a little dated"
The price is SAR 671
SAR 812 total
includes taxes & fees
2 Mar - 3 Mar
The Black Bear Lodge at Stratton Mountain 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, (665)
"Our large family with kids stayed here for ski vacation. Comfortable beds , clean rooms. Kitchen fully stuffed with necessary kitchen items. 40 minutes drive from Killington. Kids enjoyed the pool. Will be back for sure "
The price is SAR 559
SAR 660 total
includes taxes & fees
3 Feb - 4 Feb
Holiday Inn Club Vacations Mount Ascutney Resort, an IHG Hotel
Mount Snow Grand Summit Resort
Exterior

Mount Snow Grand Summit Resort

3.0 star property
8.8 out of 10, Excellent, (178)
"Older, air drying in the locker rooms odd . Moisture. "
The price is SAR 1,103
SAR 1,320 total
includes taxes & fees
3 Mar - 4 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 SAR 596
SAR 843 total
includes taxes & fees
9 Feb - 10 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 SAR 596
SAR 843 total
includes taxes & fees
9 Feb - 10 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 SAR 596
SAR 843 total
includes taxes & fees
9 Feb - 10 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 SAR 596
SAR 843 total
includes taxes & fees
9 Feb - 10 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 SAR 596
SAR 843 total
includes taxes & fees
9 Feb - 10 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 SAR 671
SAR 941 total
includes taxes & fees
9 Feb - 10 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 SAR 671
SAR 941 total
includes taxes & fees
9 Feb - 10 Feb
Palmer House Resort - Deluxe Two Double Beds 3
Deluxe 2xQueen- 2nd floor in Historic Inn
jtkjk8gam1jmctxpm2wj

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 SAR 815
SAR 1,227 total
includes taxes & fees
5 Feb - 6 Feb
Deluxe 2xQueen- 2nd floor in Historic Inn
Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
FarmRoadEstate-156

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 SAR 1,548
SAR 2,138 total
includes taxes & fees
5 Mar - 6 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 SAR 671
SAR 941 total
includes taxes & fees
9 Feb - 10 Feb
Palmer House Resort - Deluxe Two Double Beds 5
Deluxe King Room w/fireplace and separate entrance
nnnxeovq8plvhq8njjdu

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 SAR 901
SAR 1,329 total
includes taxes & fees
5 Feb - 6 Feb
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 SAR 945
SAR 1,388 total
includes taxes & fees
5 Feb - 6 Feb
Deluxe King, kitchenette, fireplace
King with Bunk Bed- 2nd floor in Historic Inn
bdpkcwte2m2y2mxeajkq

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 SAR 729
SAR 1,121 total
includes taxes & fees
25 Feb - 26 Feb
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 SAR 671
SAR 941 total
includes taxes & fees
9 Feb - 10 Feb
Palmer House Resort - Deluxe Two Double Beds 2
Deluxe King - 2nd floor in Historic Inn
dsc-1471

Deluxe King - 2nd floor in Historic Inn

The price is SAR 858
SAR 1,282 total
includes taxes & fees
5 Feb - 6 Feb
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.
Don't see what you're looking for?
See all available properties in Chester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chester

Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
Cabin with Spring snow!

Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!

9.8 out of 10, Exceptional, (73)
"This cabin was the perfect little spot for a New Years vacation. It’s easy to get to, has parking on site, and is a short drive to get groceries, some shops in town, and more. We loved the nostalgic feel of the appliances and decor, including the retro Nintendo comforter! We cooked all of our meals while here, the stove and oven worked well and there were plenty of pots, pans, etc. The fireplace was easy to use and warmed the entire place well, even during a snowstorm. We made good use to the CD...
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
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, (21)
"The property is along a well maintained dirt road, which our little EV had no trouble navigating. The cabin stayed very warm, and with no neighbors around it was very peaceful. We had no cell service at the cabin but the wifi worked well, and the hosts provided great communication. Our family had a great time."
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 SAR 1,524
SAR 1,895 total
includes taxes & fees
3 Mar - 4 Mar
Long Trail House at Stratton Mountain Resort
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, an IHG Hotel - 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. Bonnie’s Bundles Dolls offers fun for the whole family, while Okemo Mountain Resort is one of the most popular places to visit nearby. In the area, other attractions include DaVallia Art & Accents and Stratton Mountain Resort.
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.