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Best Resorts in Chester

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Check prices for these dates

Next weekend
Aug 21 - Aug 23
In two weeks
Aug 28 - Aug 30
In one month
Sep 11 - Sep 13
In two months
Oct 9 - Oct 11

Our top choices for Chester resorts

Exterior

1. 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, (864 reviews)
"It was clean an convenient"
United States
Russell
$154 nightly
The price is $168
Aug 17 - Aug 18
Total with taxes and fees
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
WiFi (free), bed sheets

2. 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, (1,005 reviews)
"Amazing hotel"
United States
Luis
$129 nightly
The price is $142
Sep 13 - Sep 14
Total with taxes and fees
The Black Bear Lodge at Stratton Mountain Resort
Lobby

3. Woodstock Inn & Resort

Woodstock Inn & Resort
4.5 star property
Woodstock
9.4 out of 10, Exceptional, (598 reviews)
"As always - best hotel in Vermont."
United States
ben
$436 nightly
The price is $479
Sep 7 - Sep 8
Total with taxes and fees
Woodstock Inn & Resort
Exterior

4. Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property
3.0 star property
West Dover
8.6 out of 10, Excellent, (301 reviews)
"Beautiful property, very helpful staff"
United States
Jak
$161 nightly
The price is $176
Sep 15 - Sep 16
Total with taxes and fees
Grand Summit Resort, A Vail Resorts Property
Exterior

5. Deluxe King, kitchenette, fireplace

Deluxe King, kitchenette, fireplace
West Dover
10.0 out of 10, Exceptional, (4 reviews)
"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.
$437 nightly
The price is $478
Aug 19 - Aug 20
Total with taxes and fees
Deluxe King, kitchenette, fireplace
1 bedroom, iron/ironing board, WiFi

6. Deluxe 2xQueen- 2nd floor in Historic Inn

Deluxe 2xQueen- 2nd floor in Historic Inn
West Dover
10.0 out of 10, Exceptional, (5 reviews)
"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.
$372 nightly
The price is $405
Aug 17 - Aug 18
Total with taxes and fees
Deluxe 2xQueen- 2nd floor in Historic Inn
Exterior

7. 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 reviews)
"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
$437 nightly
The price is $478
Aug 17 - Aug 18
Total with taxes and fees
Deluxe King, Living Room w/sofa bed, bunk bed & fireplace
1 bedroom, iron/ironing board, WiFi

8. Deluxe 2xQueen & fireplace

Deluxe 2xQueen & fireplace
Dover
10.0 out of 10, Exceptional, (1 review)
"Beautiful Inn however, the fridge should be lifted off the floor. It’s too low. A small broom and dust pan would be nice to sweep up the dirt that treks in from the dirt parking lot and walk ways. Upgrade full size beds to at least two Queen size beds."
United States
Christina R.
$372 nightly
The price is $405
Aug 17 - Aug 18
Total with taxes and fees
Deluxe 2xQueen & fireplace
Dining

9. Deluxe King Room w/pull-out love seat and fireplace

Deluxe King Room w/pull-out love seat and fireplace
Dover
10.0 out of 10, Exceptional, (2 reviews)
"Place was perfect"
United States
James R.
$411 nightly
The price is $449
Aug 17 - Aug 18
Total with taxes and fees
Deluxe King Room w/pull-out love seat and fireplace
Exterior

10. 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 reviews)
"Very well apportioned room. Super clean and comfortable. Restaurant was delicious. Bartender is cool to chat with."
United States
Forrest W.
$411 nightly
The price is $449
Aug 17 - Aug 18
Total with taxes and fees
King with Bunk Bed- 2nd floor in Historic Inn
1 bedroom, iron/ironing board, WiFi

11. Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance

Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance
Dover
10.0 out of 10, Exceptional, (2 reviews)
"The place was clean, cozy and comfortable. The whole estate is beautiful."
United States
Mike T.
$437 nightly
The price is $478
Aug 17 - Aug 18
Total with taxes and fees
Deluxe King Suite, Living Room area w/sofa bed & fireplace, private entrance
1 bedroom, iron/ironing board, WiFi

12. Deluxe 2xQueen in Historic Inn

Deluxe 2xQueen in Historic Inn
West Dover
8.0 out of 10, Very Good, (1 review)
$372 nightly
The price is $405
Aug 19 - Aug 20
Total with taxes and fees
Deluxe 2xQueen in Historic Inn
Exterior

13. Luxury King w/balcony, accessible

Luxury King w/balcony, accessible
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"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.
$411 nightly
The price is $449
Aug 19 - Aug 20
Total with taxes and fees
Luxury King w/balcony, accessible
Exterior

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

Luxury King Suite, Living Room w/sofa bed and jacuzzi tub
West Dover
10.0 out of 10, Exceptional, (2 reviews)
"Such a quaint, beautiful Spot. It’s uniqueness, historic feel and common area was very warming. Personnel was very friendly and attentive"
United States
Jessica
$411 nightly
The price is $449
Aug 17 - Aug 18
Total with taxes and fees
Luxury King Suite, Living Room w/sofa bed and jacuzzi tub
Exterior

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

Deluxe King Suite, Living Room w/sofa bed & fireplace
West Dover
10.0 out of 10, Exceptional, (1 review)
"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"
United States
Megan M.
$437 nightly
The price is $478
Aug 17 - Aug 18
Total with taxes and fees
Deluxe King Suite, Living Room w/sofa bed & fireplace
Exterior

16. Deluxe King, Living Room w/sofa bed & fireplace

Deluxe King, Living Room w/sofa bed & fireplace
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Had a really nice time - the place was lovely. They had some on property activities and were very close to the mountain. We had a great time and would definitely stay here again if back in the area!"
United States
Taylor G.
$437 nightly
The price is $478
Aug 17 - Aug 18
Total with taxes and fees
Deluxe King, Living Room w/sofa bed & fireplace
Interior

17. Deluxe Queen Suite with pull-out love seat, private entrance

Deluxe Queen Suite with pull-out love seat, private entrance
Dover
$372 nightly
The price is $405
Aug 17 - Aug 18
Total with taxes and fees
Deluxe Queen Suite with pull-out love seat, private entrance
Interior

18. Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance

Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
Dover
9.8 out of 10, Exceptional, (7 reviews)
"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."
United States
Sydney W.
$486 nightly
The price is $532
Aug 18 - Aug 19
Total with taxes and fees
Luxury King Cottage, 2 twin beds in loft, fireplace, private entrance
Exterior

19. Deluxe King- 2nd floor in Historic Inn

Deluxe King- 2nd floor in Historic Inn
West Dover
$411 nightly
The price is $449
Aug 17 - Aug 18
Total with taxes and fees
Deluxe King- 2nd floor in Historic Inn
1 bedroom, iron/ironing board, WiFi

20. 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 review)
"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.
$411 nightly
The price is $449
Aug 17 - Aug 18
Total with taxes and fees
Luxury King Suite, Living Room w/sofa bed, balcony, & 1.5 baths
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
"We loved this hotel, really nice amenities, great rooms. I wish we had planned less activities and spent more time at the hotel. If you want to stay in the hotel, plan to spend a day in the hotel. Breakfast ends at 11 and bar closes at around 10 depending on crowd."
Gabriel 2-night trip
Posted 3 hours ago
The Equinox Golf Resort & Spa

Find out more about Chester

Chester Resorts information

Number of reviews
2,807
Accommodation
28 Resorts
Lowest Price
$142
Highest Price
$532

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 bar, an outdoor tennis court, and a restaurant. Grand Summit Resort, A Vail Resorts Property - Ski resort, 5-minute walk from Green Mountain National Forest. 25.5 mi (41 km) from Chester. Enjoy the ski-in/ski-out access, spa, and fitness center. The Equinox Golf Resort And Spa - Luxury resort, 5-minute walk from Green Mountain National Forest. 25 mi (40.3 km) from Chester. Amenities include 4 restaurants, 2 bars, and a golf course. The Black Bear Lodge at Stratton Mountain Resort - Ski resort, 5-minute walk from Green Mountain National Forest. 18.7 mi (30.1 km) from Chester. Access to 10 restaurants, 2 bars, and a sauna.
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 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.

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