Search Resorts in Chester

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec
In one month
2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

Resorts in Chester

Exterior
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3.0 star property
Brownsville
9.0 out of 10, Wonderful, (777)
"Very welcoming, spacious, clean. Perfect for a family of 4. "
United States
Kathleen
The price is SAR 349
SAR 431 total
includes taxes & fees
8 Dec - 9 Dec
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Free WiFi, bed sheets
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

3.0 star property
Stratton
7.6 out of 10, Good, (936)
"We like that getting to Stratton Mountain and the downtown area was very walkable or easy to get there by regularly running shuttle buses."
United States
Mark
The price is SAR 598
SAR 723 total
includes taxes & fees
4 Dec - 5 Dec
The Black Bear Lodge at Stratton Mountain Resort
Front of property
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3.0 star property
West Dover
8.8 out of 10, Excellent, (243)
"Great place to stay!"
United States
Sonia
The price is SAR 579
SAR 692 total
includes taxes & fees
3 Dec - 4 Dec
Mount Snow Grand Summit Resort
Terrace/patio
Palmer House Resort - Deluxe King Bed 2

Palmer House Resort - Deluxe King Bed 2

Manchester Center,
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...
United States
Mark A.
The price is SAR 597
SAR 844 total
includes taxes & fees
8 Dec - 9 Dec
Palmer House Resort - Deluxe King Bed 2
Exterior
Deluxe 2xQueen- 2nd floor in Historic Inn

Deluxe 2xQueen- 2nd floor in Historic Inn

West Dover
10.0 out of 10, Exceptional, (5)
"Everything was just fantastic! Everyone was friendly and accommodating. Owners were so nice! Property is amazing and a great location to Mount Snow. Can not go wrong with this spot."
United States
Brendan M.
The price is SAR 557
SAR 919 total
includes taxes & fees
2 Dec - 3 Dec
Deluxe 2xQueen- 2nd floor in Historic Inn
Lobby
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 star property
Woodstock
9.2 out of 10, Wonderful, (552)
"Highly recommend stay here"
United States
Margie
The price is SAR 1,197
SAR 1,482 total
includes taxes & fees
2 Dec - 3 Dec
Woodstock Inn & Resort
Exterior
Deluxe King, kitchenette, fireplace

Deluxe King, kitchenette, fireplace

West Dover
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."
United States
john L.
The price is SAR 815
SAR 1,229 total
includes taxes & fees
2 Dec - 3 Dec
Deluxe King, kitchenette, fireplace
Exterior
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace

Deluxe King, Living Room w/sofa bed, bunk bed & fireplace

Dover
9.4 out of 10, Exceptional, (6)
"This is a beautiful, large suite in a quaint Vermont town. There are two main rooms: a bedroom with a king bed and a bunk bed, and a separate living room with a fireplace. The main inn also has lounge areas open to guests all night, and is a perfect stay for both families and couples. "
United States
Olivia
The price is SAR 902
SAR 1,336 total
includes taxes & fees
2 Dec - 3 Dec
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
Exterior
Deluxe King Room w/fireplace and separate entrance

Deluxe King Room w/fireplace and separate entrance

West Dover
10.0 out of 10, Exceptional, (4)
"We thoroughly enjoyed our one-night stay. Our room was cozy and all the staff were wonderful."
United States
Charles B.
The price is SAR 815
SAR 1,246 total
includes taxes & fees
2 Dec - 3 Dec
Deluxe King Room w/fireplace and separate entrance
Terrace/patio
Palmer House Resort - Deluxe King Bed 5

Palmer House Resort - Deluxe King Bed 5

Manchester Center, , VT, US
9.4 out of 10, Exceptional, (12)
"Lovely place to stay, kind staff and great accomodations."
United States
Nicolas S.
The price is SAR 597
SAR 844 total
includes taxes & fees
8 Dec - 9 Dec
Palmer House Resort - Deluxe King Bed 5
Terrace/patio
Palmer House Resort - Deluxe King Bed 1

Palmer House Resort - Deluxe King Bed 1

Manchester Center,
8.0 out of 10, Very Good, (4)
"It was a beautiful stay. Lovely Accommodations. "
United States
Linda P.
The price is SAR 597
SAR 844 total
includes taxes & fees
8 Dec - 9 Dec
Palmer House Resort - Deluxe King Bed 1
Terrace/patio
Palmer House Resort - Deluxe King Bed 3

Palmer House Resort - Deluxe King Bed 3

Manchester Center,
8.8 out of 10, Excellent, (5)
"Efficient and helpful staff. Great location. "
United States
Kevin
The price is SAR 597
SAR 844 total
includes taxes & fees
8 Dec - 9 Dec
Palmer House Resort - Deluxe King Bed 3
Terrace/patio
Palmer House Resort - Deluxe Two Double Beds 2

Palmer House Resort - Deluxe Two Double Beds 2

Manchester Center,
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...
United States
Bridget N.
The price is SAR 672
SAR 941 total
includes taxes & fees
8 Dec - 9 Dec
Palmer House Resort - Deluxe Two Double Beds 2
Interior
Luxury King with balcony

Luxury King with balcony

West Dover
The price is SAR 513
SAR 867 total
includes taxes & fees
2 Dec - 3 Dec
Luxury King with balcony
Terrace/patio
Palmer House Resort - Deluxe Two Double Beds 4

Palmer House Resort - Deluxe Two Double Beds 4

Manchester Center,
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."
United States
Mark S.
The price is SAR 672
SAR 941 total
includes taxes & fees
8 Dec - 9 Dec
Palmer House Resort - Deluxe Two Double Beds 4
Exterior
Luxury King w/balcony, accessible

Luxury King w/balcony, accessible

West Dover
10.0 out of 10, Exceptional, (2)
"My husband and I had a wonderful time at the Inn . our room was beautiful and we had two delicious meals in the restaurant I would definitely recommend this Inn to anyone traveling in southern Vermont."
United States
Kimberley B.
The price is SAR 513
SAR 858 total
includes taxes & fees
3 Dec - 4 Dec
Luxury King w/balcony, accessible
Terrace/patio
Palmer House Resort - Deluxe King Bed 4

Palmer House Resort - Deluxe King Bed 4

Manchester Center,
6.0 out of 10, (2)
"Great prices"
United States
Peter T.
The price is SAR 597
SAR 844 total
includes taxes & fees
8 Dec - 9 Dec
Palmer House Resort - Deluxe King Bed 4
Exterior
King with Bunk Bed- 2nd floor in Historic Inn

King with Bunk Bed- 2nd floor in Historic Inn

West Dover
10.0 out of 10, Exceptional, (2)
"Very well apportioned room. Super clean and comfortable. Restaurant was delicious. Bartender is cool to chat with."
United States
Forrest W.
The price is SAR 557
SAR 919 total
includes taxes & fees
2 Dec - 3 Dec
King with Bunk Bed- 2nd floor in Historic Inn
Exterior
Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths

Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths

West Dover
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."
United States
Craig C.
The price is SAR 600
SAR 974 total
includes taxes & fees
2 Dec - 3 Dec
Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
Exterior
Deluxe King- 2nd floor in Historic Inn

Deluxe King- 2nd floor in Historic Inn

West Dover
The price is SAR 513
SAR 867 total
includes taxes & fees
2 Dec - 3 Dec
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.
View all properties

White Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Jackson Gore Village

Jackson Gore Village

10/10 Excellent
"Very clean, everyone was so nice. Food at restaurant is a little pricey but was very good. "
William 2-night trip
Posted 1 day ago
Jackson Gore Village

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. Mount Snow Grand Summit Resort - Ski resort, 5-minute walk from Mount Snow. 25.5 mi (41 km) from Chester. Has ski-in/ski-out access, a full-service spa, and a fitness center. Holiday Inn Club Vacations Mount Ascutney Resort by IHG - 15.4 mi (24.7 km) from Chester. Enjoy the seasonal outdoor pool, bar, and an indoor pool. 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. 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 Stratton 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.