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Chester – 12 hotels and places to stay

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Chester Inn

Chester

Located in Chester, 25 miles from Stratton Mountain, Chester Inn has accommodations with a shared lounge, free private parking and a tennis court.

T
Tammy
From
United States
Very cozy & relaxing we enjoyed sitting in the dinning area playing games felt like being home
Scored out of 10, guest rating 8.4
Very Good - What previous guests thought, 120 reviews
Price from
$179
1 night, 2 adults

The Weston Hotel

Weston (Near Chester)

Located in Weston, 16 miles from Stratton Mountain, The Weston Hotel has accommodations with a fitness center, free private parking, a shared lounge and a terrace.

G
Godfrey
From
Libya
The room was a slice of paradise in Vermont. From the linens to the bathroom and all amenities this hotel pulled out all the stops. The service was above and beyond, greeting us daily, making sure we had everything we needed and even surprising us with some delicious AM biscuits on our final morning. Will be coming back very soon!
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 9 reviews
Price from
$450
1 night, 2 adults

Best Western Springfield Hotel

Springfield (Near Chester)

Located within 11 miles of Bellows Falls Amtrak Station and 17 miles of Mount Ascutney, Best Western Springfield Hotel has rooms in Springfield.

M
Michelle
From
United States
Friendly staff, exceptionally clean and quiet. Even with a wedding party on the first floor. We never heard any noise
Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 247 reviews
Price from
$152.10
1 night, 2 adults

Dream Weaver

Ludlow (Near Chester)

Featuring a restaurant, Dream Weaver is located in Ludlow in the Vermont region, 25 miles from Killington Peak and 27 miles from Stratton Mountain.

S
Sarah
From
United States
Looked just like photo. Great, walkable neighborhood. Close to maple sugar house, cheese factory, apple cider donuts, Okemo mountain, buttermilk falls and deer leap overlook. Perfect for a two-night visit for fall foliage and seasonal treats!
Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 24 reviews
Price from
$225
1 night, 2 adults

The Upper Pass Lodge

Londonderry (Near Chester)

Located in Londonderry, 14 miles from Stratton Mountain, The Upper Pass Lodge has accommodations with a seasonal outdoor swimming pool, free private parking, a garden and a shared lounge.

R
Russell
From
United States
Everyone very friendly. We had our dog with us, for the 2nd year in a row. All are accepted there. Good food at the restaurant and even had our dog with us in the bar area.
Scored out of 10, guest rating 7.7
Good - What previous guests thought, 131 reviews
Price from
$110.60
1 night, 2 adults

Champagne Supernova

Ludlow (Near Chester)

Champagne Supernova is located in Ludlow, just 25 miles from Killington Peak and 27 miles from Stratton Mountain. The apartment has access to a restaurant.

G
Gary
From
United States
Convenient location and easy check in
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 13 reviews
Price from
$211
1 night, 2 adults

The Governor's Inn

Ludlow (Near Chester)

The Governor's Inn offers accommodations in Ludlow, 26 miles from Killington Peak and 27 miles from Stratton Mountain.

A
AgataW
From
United States
Great hosts, very nice to chat with. Very clean rooms. Fantastic breakfast.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 87 reviews
Price from
$190
1 night, 2 adults

The Pointe at Castle Hill Resort & Spa

Ludlow (Near Chester)

In the Green Mountains of Vermont, this resort has a full service spa and health club, as well as an on-site restaurant. Skiing at Okemo Mountain is just 4 miles away.

K
Kenneth
From
United States
Location was great, we didn't have breakfast. We came to VT to to have Thanksgiving with family and really liked the hotel.
Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 263 reviews
Price from
$189
1 night, 2 adults

Okemo Mountain Lodge

Ludlow (Near Chester)

Okemo Mountain Lodge offers accommodations in Ludlow, 25 miles from Killington Peak and 27 miles from Stratton Mountain. The apartment has access to a restaurant.

M
Michael
From
United States
Being able to be so close to the mountain was awesome. The condo was very accommodating, cozy and clean. I would definitely book this trip again.
Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 43 reviews
Price from
$234
1 night, 2 adults

Main and Mountain

Ludlow (Near Chester)

Located in Ludlow, within 25 miles of Killington Peak and 27 miles of Stratton Mountain, Main and Mountain has accommodations with a bar and free WiFi throughout the property as well as free private...

A
Aaron
From
Aruba
Great location—staff was very helpful and the rooms were clean & comfortable. We would definitely stay there again!
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 42 reviews
Price from
$307.80
1 night, 2 adults
See all 12 hotels in Chester

Best hotels with breakfast in Chester and nearby

Private Chester Home with Deck, Mins to Skiing! offers accommodations in Chester, 27 miles from Mount Tom and 9.1 miles from Dorsey Park.

Vermont Ski and Stay is located in Springfield, just 30 miles from Mount Tom and 12 miles from Bellows Falls Amtrak Station. This property offers access to a balcony and free private parking.

From $421.36 per night

Hotels located in the center of Chester

Chester Farmhouse on 100 Acres, 15 Min to Okemo! offers accommodations in Chester, 7.9 miles from Dorsey Park and 21 miles from Bellows Falls Amtrak Station.

What Guests Said About Chester:

8.0

Chester is a cute town with a number of charming B&Bs and...

Chester is a cute town with a number of charming B&Bs and shops. There are a number of decent restaurants in/around Chester, though not much of a "fine dining" selection. There are a number of outdoorsy things to do, like hiking in warm weather and skiing in winter.
Guest review by
Arthur
United States
6.0

Chester seemed like a nice historic town with a laid back...

Chester seemed like a nice historic town with a laid back approach to life. We did not visit any other sites there because we had a wedding up the road. I would probably not stay at the Inn again due to no tv, no air conditioning and no elevator.
Guest review by
Jennifer

See reviews by guests who stayed at hotels in Chester

See all
Scored out of 10, guest rating 6.6
Pleasant - What previous guests thought, 165 reviews
Hotel was well placed for our tour of New England. Lovely, big entrance area with comfortable seating and imposing fireplace. Restaurant served very good food from an extensive menu with very pleasant staff. Breakfast was reasonably good if you were not too late (see below). Hotel was easy to find with good parking directly outside.
Guest review by
Malcolm
United Kingdom
Scored out of 10, guest rating 6.6
Pleasant - What previous guests thought, 165 reviews
The hotel looked wonderful from outside, decorated with lights, basically one of the most beautiful houses in the town. Spacious lobby with lots of tips for Vermont-based activities. Staff was kind to us. There is a perfect Pie Shop and Cafe next door.
Guest review by
Matej
Czech Republic
Scored out of 10, guest rating 6.6
Pleasant - What previous guests thought, 165 reviews
An old-style hotel and helpful and friendly staff. Generous breakfast spread.. l would have liked to have tried the restaurant for dinner but train arrival in Bellows Falls did not allow.
Guest review by
Linda
United States
Scored out of 10, guest rating 6.6
Pleasant - What previous guests thought, 165 reviews
The traditional style hotel is centrally located in the quiet little town. The staff were very nice, and helpful. I enjoyed my evening meal in the restaurant. I would stay there again.
Guest review by
David
Canada
From $135.16 per night
Scored out of 10, guest rating 8.4
Very Good - What previous guests thought, 120 reviews
The town of Chester was really cute. The room was very clean. The coffee bar in the kitchen was well stocked and and there was a nice room to play games or do puzzles.
Guest review by
Nikol
United States