Search hotels in Chester, MA

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Chester – 1 hotel or place to stay

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Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts

Chester

Vintage Caboose Rental in Historic Small Town near Springfield, Massachusetts is located in Chester, just 22 miles from Tanglewood and 23 miles from Norman Rockwell Museum.

Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 6 reviews
Price from
$86.10
1 night, 2 adults

Berkshire Lake Lodge

Becket (Near Chester)

Located in Becket, within 8 miles of Cranwell Spa & Golf Club and 10 miles of Tanglewood Musical Center, Berkshire Lake Lodge has accommodations with water sports facilities and free WiFi throughout...

P
Paul
From
United States
Amazing hospitality!! Definitely worth it!
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 30 reviews
Price from
$149.50
1 night, 2 adults

Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires

South Lee (Near Chester)

Located in South Lee and within 5 mi of Norman Rockwell Museum, Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires has barbecue facilities and nonsmoking rooms.

Y
Yehonatan
From
Israel
Great place with good pool and mini golf. Nice trails around the hotel
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 731 reviews
Price from
$139.50
1 night, 2 adults

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Lee (Near Chester)

The Black Swan Inn, Ascend Hotel Collection is conveniently located in the foothills of the Berkshire Mountains.

c
ceren
From
Turkey
My husband and I stayed here for New Year's Eve, and loved it so much that we extended our stay another night! The staff was very friendly and helpful with everything. The rooms were comfortable and clean. You can buy some snacks and drinks at the reception and the food at the Indian restaurant was amazing!
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 543 reviews
Price from
$120.70
1 night, 2 adults

Chambery Inn

Lee (Near Chester)

This historic Massachusetts bed and breakfast features free Wi-Fi access and a beautiful front yard. Cable TV and a private bathroom are featured in every uniquely styled room.

S
Scott
From
United States
The room- very nice room. Felt like home.
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 24 reviews
Price from
$299.99
1 night, 2 adults

Devonfield Inn

Lee (Near Chester)

Devonfield Inn in Lee provides accommodations with a garden, a terrace, and a shared lounge.

Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 13 reviews
Price from
$359
1 night, 2 adults

Elm Motel

Westfield (Near Chester)

This motel offers refrigerators in each room and free parking. It is located within a 5 - minute drive of Interstate 90 and 10 miles from Six Flags Amusement Park and Blandford Ski Area.

K
Kathleen
From
United States
Staff very friendly, place was newly remodeled and very clean.
Scored out of 10, guest rating 6.9
Pleasant - What previous guests thought, 218 reviews
Price from
$89
1 night, 2 adults

Quality Inn Lee - Lenox South

Lee (Near Chester)

Quality Inn Lee - Lenox South has accommodations in Lee. This 4-star inn offers free WiFi. The property is non-smoking throughout and is located 3.6 miles from Cranwell Spa & Golf Club.

D
Denise
From
Belgium
The breakfast was great: a lot of choice, very good coffee, spacious place; large room with two King size beds very comfortable ! A lot of restaurants nearby.
Scored out of 10, guest rating 7.9
Good - What previous guests thought, 368 reviews
Price from
$89.59
1 night, 2 adults

Econo Lodge Lee - Great Barrington

Lee (Near Chester)

Located in Lee, 5.4 miles from Norman Rockwell Museum and 5.9 miles from Cranwell Spa & Golf Club, Econo Lodge Lee - Great Barrington has mountain views and free WiFi.

A
Andrea
From
United States
Property was cute, everything looks newer / fresh like the floor wasn’t old the shower wasn’t old etc, property is definitely well maintained and cleaned thoroughly after the guests!
Scored out of 10, guest rating 6.6
Pleasant - What previous guests thought, 229 reviews
Price from
$69.30
1 night, 2 adults

Sunset Inn

Lee (Near Chester)

Offering an outdoor swimming pool, Sunset Inn is located in Lee, Massachusetts just 10 minutes’ drive from Tanglewood music venue. Free Wi-Fi access is available.

W
William
From
United States
Everything the staff was nice and perfect room was nice
Scored out of 10, guest rating 7.4
Good - What previous guests thought, 61 reviews
Price from
$110
1 night, 2 adults
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