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Chester – 11 hotels and places to stay

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Chester Inn

Chester

Located in Chester, 24 miles from Stratton Mountain, Chester Inn has accommodations with a shared lounge, free private parking and a tennis court.

F
Filinto
From
Brazil
Very nice house. The kitchen very clean and complete.
Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 151 reviews
Price from
$114.10
1 night, 2 adults

Stone Hearth Inn and Eatery

Chester

Stone Hearth Inn and Eatery offers accommodations in Chester, 23 miles from Stratton Mountain and 28 miles from Mount Equinox. This bed and breakfast offers free private parking and daily room...

K
Katie
From
United States
This was a great bed and breakfast! Would definitely stay again. The food in the restaurant was so good and the inn was lovely.
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 73 reviews
Price from
$230.25
1 night, 2 adults

The Weston Hotel

Weston (Near Chester)

Located in Weston, 15 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, 14 reviews
Price from
$395
1 night, 2 adults

The Upper Pass Lodge

Londonderry (Near Chester)

Located in Londonderry, 12 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 8.0
Very Good - What previous guests thought, 144 reviews
Price from
$99.99
1 night, 2 adults

Best Western Springfield Hotel

Springfield (Near Chester)

Located in Springfield and with Bellows Falls Amtrak Station reachable within 11 miles, Best Western Springfield Hotel has a fitness center, non-smoking rooms, free WiFi throughout the property and a...

K
Karen
From
United States
Breakfast was decent. Lots of choices. Hot food, cold food, and fruit, hard boiled eggs.
Scored out of 10, guest rating 8.8
Excellent - What previous guests thought, 218 reviews
Price from
$152.10
1 night, 2 adults

Birch House: Cozy Cabin 5 min from Okemo

Ludlow (Near Chester)

Birch House: Cozy Cabin 5 min from Okemo in Ludlow features accommodations with free Wifi, 23 miles from Killington Peak, 24 miles from Stratton Mountain, and 25 miles from Gifford Woods State Park.

S
Staci
From
United States
A door code was emailed to me a few days before arrival!
Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 8 reviews
Price from
$396
1 night, 2 adults

Main and Mountain

Ludlow (Near Chester)

Located in Ludlow, within 25 miles of Killington Peak and 26 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 9.1
Wonderful - What previous guests thought, 45 reviews
Price from
$162.18
1 night, 2 adults

Snowdon Chalet Motel

Londonderry (Near Chester)

Located in Londonderry, 12 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 9.2
Wonderful - What previous guests thought, 98 reviews
Price from
$154.80
1 night, 2 adults

The Governor's Inn

Ludlow (Near Chester)

The Governor's Inn offers accommodations in Ludlow, 25 miles from Killington Peak and 26 miles from Stratton Mountain.

C
Carlos
From
United States
The staff is awesome, always ready to assist. The breakfast is memorable.
Scored out of 10, guest rating 9.7
Exceptional - What previous guests thought, 66 reviews
Price from
$201
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 8.2
Very Good - What previous guests thought, 228 reviews
Price from
$169
1 night, 2 adults
See all 11 hotels in Chester

Budget hotels in Chester and nearby

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Gorgeous Tent Rental for Vermont Getaways in Nature offers accommodations in Springfield, 31 miles from Mount Tom and 9.3 miles from Bellows Falls Amtrak Station.

Fabulous Vermont Glamping Getaway on a Farm is located in Springfield, just 31 miles from Mount Tom and 9.3 miles from Bellows Falls Amtrak Station.

What Guests Said About Chester:

Scored out of 10, guest rating 10

Historic town which has created a walking tour of old...

Historic town which has created a walking tour of old buildings as well as some of their more famous encounters with history. Super walkable and lots to explore both right in town and in adjoining area. Don't miss the Historical Museum in the original high school right in town.
Guest review byBerkshiresBound
Scored out of 10, guest rating 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 byArthur
United States
Scored out of 10, guest rating 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 byJennifer

See reviews by guests who stayed at hotels in Chester

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Scored out of 10, guest rating 6.6
Pleasant - What previous guests thought, 104 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 byMalcolm
United Kingdom
Scored out of 10, guest rating 6.6
Pleasant - What previous guests thought, 104 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 byMatej
Czech Republic
Scored out of 10, guest rating 6.6
Pleasant - What previous guests thought, 104 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 byLinda
United States
Scored out of 10, guest rating 6.6
Pleasant - What previous guests thought, 104 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 byDavid
Canada
From $124.37 per night
Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 151 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 byNikol
United States

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