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19 Sep - 21 Sep
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26 Sep - 28 Sep
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10 Oct - 12 Oct
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7 Nov - 9 Nov

Resorts in Chester

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, (739)
"Great place to stay and see the beautiful mt ascutney "
The price is SAR 571
SAR 673 total
includes taxes & fees
14 Sep - 15 Sep
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
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, (913)
"Great accommodation for wedding "
The price is SAR 542
SAR 656 total
includes taxes & fees
14 Sep - 15 Sep
The Black Bear Lodge at Stratton Mountain Resort
Mount Snow Grand Summit Resort
Exterior

Mount Snow Grand Summit Resort

3.0 star property
8.8 out of 10, Excellent, (222)
"Our room was clean and comfortable .The hot tub, sauna and heated pool were very enjoyable. Staff was kind and responsive. Amazing location!"
The price is SAR 638
SAR 764 total
includes taxes & fees
9 Oct - 10 Oct
Mount Snow Grand Summit Resort
Equinox Resort Residences
Lobby sitting area

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 SAR 3,846
SAR 5,412 total
includes taxes & fees
30 Sep - 1 Oct
Equinox Resort Residences
Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (532)
"Always a stunning stay in Woodstock!"
The price is SAR 2,247
SAR 2,637 total
includes taxes & fees
14 Sep - 15 Sep
Woodstock Inn & Resort
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 SAR 784
SAR 1,085 total
includes taxes & fees
17 Sep - 18 Sep
Palmer House Resort - Deluxe King Bed 3
Deluxe 2xQueen- 2nd floor in Historic Inn
Exterior

Deluxe 2xQueen- 2nd floor in Historic Inn

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."
The price is SAR 686
SAR 1,078 total
includes taxes & fees
11 Sep - 12 Sep
Deluxe 2xQueen- 2nd floor in Historic Inn
Deluxe King, kitchenette, fireplace
Exterior

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 815
SAR 1,225 total
includes taxes & fees
11 Sep - 12 Sep
Deluxe King, kitchenette, fireplace
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
Exterior

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

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. "
The price is SAR 902
SAR 1,332 total
includes taxes & fees
11 Sep - 12 Sep
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
Deluxe King Room w/fireplace and separate entrance
Exterior

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 1,031
SAR 1,685 total
includes taxes & fees
18 Sep - 19 Sep
Deluxe King Room w/fireplace and separate entrance
Luxury King w/balcony, accessible
Exterior

Luxury King w/balcony, accessible

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."
The price is SAR 643
SAR 1,018 total
includes taxes & fees
11 Sep - 12 Sep
Luxury King w/balcony, accessible
King with Bunk Bed- 2nd floor in Historic Inn
Exterior

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 1,134 total
includes taxes & fees
11 Sep - 12 Sep
King with Bunk Bed- 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 SAR 784
SAR 1,085 total
includes taxes & fees
17 Sep - 18 Sep
Palmer House Resort - Deluxe King Bed 2
Deluxe King Suite, Living Room w/sofa bed & fireplace
Exterior

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

10.0 out of 10, Exceptional, (1)
"My husband and I really enjoyed the accommodations. Great location with tons do do nearby. The place was so cozy and inviting. Would definitely stay again"
The price is SAR 815
SAR 1,225 total
includes taxes & fees
11 Sep - 12 Sep
Deluxe King Suite, Living Room w/sofa bed & fireplace
Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
Exterior

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

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."
The price is SAR 729
SAR 1,134 total
includes taxes & fees
11 Sep - 12 Sep
Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
Luxury King with balcony
Interior

Luxury King with balcony

The price is SAR 643
SAR 1,026 total
includes taxes & fees
11 Sep - 12 Sep
Luxury King with balcony
Deluxe King- 2nd floor in Historic Inn
Exterior

Deluxe King- 2nd floor in Historic Inn

The price is SAR 513
SAR 867 total
includes taxes & fees
11 Sep - 12 Sep
Deluxe King- 2nd floor in Historic Inn
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 SAR 859
SAR 1,174 total
includes taxes & fees
16 Sep - 17 Sep
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)
"Excellent hospitality, friendly staff, quality stay."
The price is SAR 784
SAR 1,085 total
includes taxes & fees
17 Sep - 18 Sep
Palmer House Resort - Deluxe King Bed 5
Luxury King Suite, Living Room w/sofa bed and jacuzzi tub
Exterior

Luxury King Suite, Living Room w/sofa bed and jacuzzi tub

10.0 out of 10, Exceptional, (2)
"Such a quaint, beautiful Spot. It’s uniqueness, historic feel and common area was very warming. Personnel was very friendly and attentive"
The price is SAR 729
SAR 1,125 total
includes taxes & fees
11 Sep - 12 Sep
Luxury King Suite, Living Room w/sofa bed and jacuzzi 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.
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Top Chester Hotel Reviews

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

10/10 Excellent
"Historical Landmark. The building is full of history. The service and amenities are wonderful especially considering the history of the building. Beautiful place to stay, relax, and unwind. Mountain views are spectacular. Restaurants are wonderful. Everything is convenient. Staff are friendly and welcoming. I am very happy and would recommend this place to anyone. "
Janine Louise 4-night trip
Posted 2 weeks ago
The Equinox Golf Resort & Spa

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. 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. DaVallia Art & Accents and Bonnie's Bundles Dolls are a few of the interesting sights to visit. In the area, other attractions include Vermont Museum of Mining and Minerals 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.