Browse the Best Chester Resorts from CA $204

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

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Our top choices for Chester resorts

1. Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Brownsville

Russell

CA $234 total

includes taxes & fees

Sep 1 - Sep 2

2. The Black Bear Lodge at Stratton Mountain Resort

Stratton

Roberta

CA $204 total

includes taxes & fees

Sep 3 - Sep 4

3. Woodstock Inn & Resort

Woodstock

ben

CA $687 total

includes taxes & fees

Sep 7 - Sep 8

4. Grand Summit Resort, A Vail Resorts Property

West Dover

Daniel

CA $250 total

includes taxes & fees

Sep 30 - Oct 1

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

West Dover

Brendan M.

CA $661 total

includes taxes & fees

Sep 1 - Sep 2

6. Deluxe King, kitchenette, fireplace

West Dover

john L.

CA $762 total

includes taxes & fees

Sep 1 - Sep 2

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

Dover

Olivia

CA $762 total

includes taxes & fees

Sep 1 - Sep 2

8. Deluxe 2xQueen & fireplace

Dover

Christina R.

CA $661 total

includes taxes & fees

Sep 3 - Sep 4

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Top Chester Hotel Reviews

Colonial Motel

10/10 Excellent

"Staff was very helpful. A little seating area under some trees was a beautiful place to relax while the sun was setting."

Hampton Inn and Suites Manchester

10/10 Excellent

"WOW! Nicest Hampton Inn ever! The manager Stacy is over the top cordial, professional and helpful. I highly recommend this stay. Nice breakfast and all of the employees are doing a great job. Fun shopping nearby and great restaurant selections too. I would not hesitate to book a stay here again in the future."

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

10/10 Excellent

"There was a lot to love about Holiday Inn Club Vacations Mount Ascutney, especially for a larger family or group. Our three-bedroom villa was BY FAR the largest accommodation of our trip and surprisingly affordable. We had tons of room to spread out, a decent-sized kitchen for cooking, and FREE laundry—a huge win during a long road trip! The villa kitchen was helpful but pretty minimally stocked. Cooking utensils and cutting boards were lacking, so bring some basics if you plan to cook. Grills are available, but you’ll need charcoal. I’d recommend buying it and any groceries before arriving because the onsite marketplace is expensive. The biggest disappointment was the pool, which is closed through 2027. Traveling with kids, that was a major bummer and definitely something families should know before booking. The location is incredibly beautiful, tucked away on a Vermont mountainside, but it is truly in the middle of nowhere. Come prepared! Overall, the incredible amount of space and affordability made it work really well for our group. It wasn’t our favorite stay of the trip, but the value for a three-bedroom villa was hard to beat."

On The River Inn

10/10 Excellent

"This was one of the nicest hotels I have ever stayed in! We had a river view room with rocking chairs on the balcony, s’mores kits were offered every night (pick up by the front desk) and 2 fire pits to choose from. Game room was cute (although the air hockey table’s fan wasn’t strong on one side), library was absolutely gorgeous. Loved having water refilling stations on 2 of the 3 floors and 24/7 coffee/tea stations, too. Queen beds were very comfy, and the room was so spacious. I’d love another piece of furniture with drawers to keep our stuff though - we lived out of our suitcases because there was only an armoire with 3 half drawers. And maybe another towel bar or hooks in the bathroom to hang the towels to dry, especially if you have 4 people in a room. Breakfast buffet (included with our Expedia stay but extra for others) was always hot & fresh. We had 4 breakfasts: French toast, pancakes, waffles, french toast again. There was always fresh homemade pastries and muffins, yogurt, and oatmeal. I would have loved some fresh fruit like berries to go with the yogurt instead of apples and oranges. Staff was always so nice and helpful, especially at breakfast. Housekeeping forgot twice to give us the 4 fresh towels (gave 3 instead) but we got replacements when we asked at the desk."

Find out more about Chester

Chester Resorts information

Number of reviews	869
Accommodation	28 Resorts
Lowest Price	CA $204
Highest Price	CA $687

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 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. King with Bunk Bed- 2nd floor in Historic Inn - Situated just 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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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester resorts

1. Holiday Inn Club Vacations Mount Ascutney Resort by IHG