Browse the Best Chester Resorts from CA $210

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Our top choices for Chester resorts

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

Carol

CA $236 total

includes taxes & fees

Aug 9 - Aug 10

The Black Bear Lodge at Stratton Mountain Resort

Stratton

Patti

CA $210 total

includes taxes & fees

Aug 16 - Aug 17

Woodstock Inn & Resort

Woodstock

ben

CA $802 total

includes taxes & fees

Jul 20 - Jul 21

Grand Summit Resort, A Vail Resorts Property

West Dover

Jordyn C

CA $257 total

includes taxes & fees

Jul 20 - Jul 21

Deluxe 2xQueen- 2nd floor in Historic Inn

West Dover

Brendan M.

CA $566 total

includes taxes & fees

Jul 21 - Jul 22

Deluxe King, kitchenette, fireplace

West Dover

john L.

CA $658 total

includes taxes & fees

Jul 21 - Jul 22

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

Dover

Olivia

CA $658 total

includes taxes & fees

Jul 21 - Jul 22

Deluxe 2xQueen & fireplace

Dover

Christina R.

CA $558 total

includes taxes & fees

Jul 21 - Jul 22

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Top Chester Hotel Reviews

Hampton Inn Brattleboro

10/10 Excellent

"Clean, comfortable and fairly priced."

Latchis Hotel

10/10 Excellent

"The uniqueness of the '30s/40's era vibe brought us back for another visit.It was like stepping back in time. The movie theaters are classic. Sages is the adjoining cocktail lounge complete with cosy,stuffed chairs,40's style decor.Again, we felt like we stepped back in time. The cocktails were quite unusual and thoughtful and we wish we could have tried them all. Tapas and waffles! So yummy. The staff at the hotel were gracious, friendly, helpful.And there was a never-ending supply of plain or cucumber ice water at the front desk. The beds were crisply sheeted and super comfy. Best part? The record player in the room with a whole library of vinyl to choose from.We enjoyed some classical tunes and some Beatles! Though the town itself has seen a bit of degradation since our last visit, with some noticably vacant store fronts, there are still some cool boutiques, art galleries and eateries.And check out the huge co-op grocery store."

Keene Elm City Hotel, an Ascend Collection Hotel

10/10 Excellent

"We had a great stay overall. The hotel was clean, well-maintained, and the staff was friendly, welcoming, and courteous throughout our visit. Breakfast was good, but the pancake station became backed up during the busy morning rush. Adding a second pancake machine would help reduce the wait and make the breakfast experience even better. We would definitely stay here again."

On The River Inn

10/10 Excellent

"Great hotel! Our room was spacious and we loved having a full size fridge and mini-kitchen. Insanely loved the bath products (sorry, I love that kind of thing!). We had a great dinner at the restaurant which has a wonderful vibe and friendly staff. When we checked in, the front desk staff forgot to mention breakfast was included (clearly I had forgotten, too)-- took me 2 days to realize that! Breakfast was great. Another plus-- the gigantic backyard/meadow adjacent to the river is stunning and smores at night were an added bonus! They do a great job creating a hotel that is perfect for families, mountain bike travelers, horse show folks, couples getaways. Hard for one place to cover all that. I had booked via an online site which I thought included all fees but there was a small daily added cost. Overall though our total expenditure was LESS than other area hotels and really, this was so beautiful, immaculate, delish and otherwise very hospitable! We will be back!"

Find out more about Chester

Chester Resorts information

Number of reviews	2,770
Accommodation	40 Resorts
Lowest Price	CA $210
Highest Price	CA $802

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 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. If you brought the kids, you can head to DaVallia Art & Accents or Bonnie's Bundles Dolls for some family fun. 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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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester resorts

Holiday Inn Club Vacations Mount Ascutney Resort by IHG