The Best Chester, VT Resorts from $162

A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

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Our top choices for Chester resorts

A multi-story hotel with a central courtyard and a reflective water feature.

1. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

Shannon

$174 nightly

Oct 26 - Oct 27

Total with taxes and fees

A hotel room with two beds, a window with blinds, a desk with a television, and a lamp.

2. The Black Bear Lodge at Stratton Mountain Resort

Stratton

DENNIS

$148 nightly

Oct 18 - Oct 19

Total with taxes and fees

A room with a checkered floor, a bench, and a fireplace.

3. Woodstock Inn & Resort

Woodstock

Ann

$479 nightly

Nov 2 - Nov 3

Total with taxes and fees

A red building with a stone fire pit and outdoor seating.

4. Grand Summit Resort, A Vail Resorts Property

West Dover

Daniel

$163 nightly

Nov 2 - Nov 3

Total with taxes and fees

A two-story house with a large porch and a pond in front.

5. Deluxe King, kitchenette, fireplace

West Dover

john L.

$372 nightly

Nov 1 - Nov 2

Total with taxes and fees

A modern bedroom with a bed, bedside tables, a dresser, and a fireplace.

6. Deluxe 2xQueen & fireplace

Dover

Christina R.

$372 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

Dover

Olivia

$398 nightly

Nov 1 - Nov 2

Total with taxes and fees

A two-story white building with a porch, labeled "Farm Road Estate Historic Inn & Cottages."

8. Deluxe King - 2nd floor in Historic Inn

West Dover

$345 nightly

Nov 1 - Nov 2

Total with taxes and fees

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Top Chester Hotel Reviews

The Manchester View

10/10 Excellent

"We arrived at the Manchester View in late September on a trip to see the beautiful change of colors. View is definitely what you get here. Surrounded by gorgeous rolling hills and mountains that were covered with green, yellow, red and orange leaves. We were celebrating our 40th anniversary and were upgraded to a suite room. Thank you! Room was very nice, clean and spacious. My only complaint was the door would stick when trying to open or close the door to the room. And, although the bath was updated and very nice, the finish work around the counter wasn't complete. There was a gap between the wall and counter the ends didn't match up to the wall. But that is just really a minor issue. They also have a continental breakfast with the basics and a nice kick off to start your day. The view, the staff and did I say the view?... We would definitely stay here again!"

The Shire Woodstock

10/10 Excellent

"We had Deluxe King River view - deluxe has a fireplace and shares a balcony with rocking chairs. The room was great except a couple little maintenance issues (I told the front desk and hope they fix). And it’s a great location walkable to downtown, great views of river and hills, and the inn has fire pits ready to go. Too bad coffee makers are in the hallway, not in the room, and there’s no breakfast (they said they might start next year). We went nearby for breakfast, and a good market is just across the street."

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"My daughter and I were looking for someplace to meet in the middle… one coming from upstate New York and one coming from Massachusetts.This was not the first hotel we looked at. Fortunately it is the one we stayed at! The facility is very nice, even though older still very well maintained. Staff was exceptional! The location was perfect for just a fun getaway weekend. The downtown area has some lovely restaurants and shops but the restaurant at the resort was also very good. We enjoyed the area so much. We're talking about going again in the winter, even though neither of us have skied in ages!"

The Jackson

10/10 Excellent

"This property is beautiful, peaceful, friendly, welcoming and far enough away from the green for a noiseless stay. The wine, cheese and bites that start your evening are lovely and gives you the opportunity to meet other guests if you choose. Ms. Walton, the host, was friendly, helpful and warm. She made me feel right at home. A magnificent place to stay in Woodstock Vermont"

On The River Inn

8/10 Good

"We had a river view suite. Trouble was you couldn’t see the river. There was to much undergrowth and trees, so you couldn’t tell there was a river there. The view from our balcony was beautiful, out onto the large lawn and a small pond. The TVs are old, so you couldn’t stream. Make sure you tell the front desk or put out your door hanger or you won’t get your room refreshed. The bar seemed open only during dinner hours. During our stay, one night the chief was “out” and they only served burgers. Breakfast was around $18, we never went down. Our room was large and bathroom adequate. It’s a 10 minute drive to town. It’a satisfactory hotel, but not worth the price."

Find out more about Chester

Chester Resorts information

Number of reviews	2,224
Accommodation	28 Resorts
Lowest Price	$162
Highest Price	$527

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. Grand Summit Resort, A Vail Resorts Property - Ski resort, 5-minute walk from Green Mountain National Forest. 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 bar, an outdoor tennis court, and restaurant. 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. Amenities include 10 restaurants, 2 bars, and a sauna. Luxury King w/balcony, accessible - Only a 5-minute walk from Green Mountain National Forest. 25.9 mi (41.7 km) from Chester. Access to a car charging station.

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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Our top choices for Chester resorts

1. Holiday Inn Club Vacations Mount Ascutney Resort by IHG