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Chester – 12 hotels and places to stay

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Stone Hearth Inn and Eatery

Chester

Stone Hearth Inn and Eatery offers accommodations in Chester, 24 miles from Stratton Mountain and 28 miles from Mount Equinox. This bed and breakfast offers free private parking and daily room...

Z
Zachary
From
United States
Staff was really friendly and the breakfast was absolutely delicious! We would absolutely stay again!
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 96 reviews
Location 9.1
Price from
$368.40
1 night, 2 adults

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.

J
Judy
From
Mexico
beautiful old house so you have to expect some creaking of floors, etc. but it was very clean, the beds were very comfortable, had a great hot shower and coffee, tea, hot chocolate for the morning. no breakfast, but everything else was very nice.
Scored out of 10, guest rating 8.4
Very Good - What previous guests thought, 110 reviews
Location 9.1
Price from
$115
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.

H
Hart
From
United States
Staff was great, they went up and beyond.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 8 reviews
Location 10.0
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 8.8
Excellent - What previous guests thought, 248 reviews
Location 9.1
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
Location 9.4
Price from
$198
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 7.9
Good - What previous guests thought, 146 reviews
Location 9.0
Price from
$124.60
1 night, 2 adults

Snowdon Chalet Motel

Londonderry (Near Chester)

Located in Londonderry, 13 miles from Stratton Mountain, Snowdon Chalet Motel provides accommodations with a garden, free private parking, a terrace and barbecue facilities.

A
Andrew
From
United Kingdom
great for a stopover or a few nights. clean with everything we needed plus snacks, too! very welcoming hosts. good rate.
Scored out of 10, guest rating 9.1
Wonderful - What previous guests thought, 109 reviews
Location 9.4
Price from
$189
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 9.3
Wonderful - What previous guests thought, 12 reviews
Location 9.9
Price from
$176
1 night, 2 adults

Birch House: Cozy Cabin 5 min from Okemo

Ludlow (Near Chester)

A recently renovated vacation home, Birch House: Cozy Cabin 5 min from Okemo offers accommodations in Ludlow.

S
Staci
From
United States
A door code was emailed to me a few days before arrival!
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 11 reviews
Location 9.4
Price from
$168.30
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, 92 reviews
Location 9.6
Price from
$190
1 night, 2 adults
See all 12 hotels in Chester

Best hotels with breakfast in Chester and nearby

  • Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 3 reviews

    Peaceful Brookside Getaway about 10 Mi to Okemo Slopes! is located in Chester, just 10 miles from Dorsey Park and 20 miles from Bellows Falls Amtrak Station.

Hotels located in the center of Chester

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
  • 10.0

    Good walking town, nice green with picnic tables.

    Good walking town, nice green with picnic tables. They have a self guided tour of the historic buildings and a well-maintained cemetery. There is a large antique store, bakery, ice rink and scenic train ride in the immediate area. The stone house village is a short drive and a must see to appreciate. The town has a nice pub within walking distance of the Inns and a tavern about one mile down the street. There are also two great restaurants within a 10 minute drive and skiing with 25 minutes.
    Guest review by
    Barbara
    United States

See reviews by guests who stayed at hotels in Chester

See all
  • From $169 per night
    Scored out of 10, guest rating 6.6
    Pleasant - What previous guests thought, 179 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
  • From $169 per night
    Scored out of 10, guest rating 6.6
    Pleasant - What previous guests thought, 179 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
  • From $169 per night
    Scored out of 10, guest rating 6.6
    Pleasant - What previous guests thought, 179 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 $169 per night
    Scored out of 10, guest rating 6.6
    Pleasant - What previous guests thought, 179 reviews
    Great location in the centre of town. Breakfast was very good and the staff were warm, welcoming and very helpful. We will for sure stay here again next time we visit Chester :)
    Guest review by
    James
    Canada
  • From $163.50 per night
    Scored out of 10, guest rating 8.4
    Very Good - What previous guests thought, 110 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