Cheap Hotels in Pittsfield

Popular Hotels in Pittsfield, Massachusetts

There are 97 cheap Hotels with Swimming Pool in and around Pittsfield, Massachusetts. Choose a hotel below or narrow your search using the filter to the right.

Berkshire Inn Image

Berkshire Inn

Pittsfield
Guest Rating: 6.6/10
(16) reviews
Swimming Pool
  1 Star
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Themes: Family-Friendly

Freebies Available
Pleasant Valley Motel West Stockbridge Image

Pleasant Valley Motel West Stockbridge

West Stockbridge
Guest Rating: 7.0/10
(97) reviews
Swimming Pool
  1 Star
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Themes: Family-Friendly

Days Inn Lenox Image

Days Inn Lenox

Lenox
Guest Rating: 6.9/10
(42) reviews
Swimming Pool
  2 Star
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Themes: Business-Friendly, Family-Friendly

Rodeway Inn Lee Image

Rodeway Inn Lee

Lee
Guest Rating: 6.1/10
(16) reviews
Swimming Pool
  2 Star
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Yankee Inn Image

Yankee Inn

Lenox
Guest Rating: 8.2/10
(64) reviews
Swimming Pool
  2 Star
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Themes: Family-Friendly, Business-Friendly

Freebies Available
Pilgrim Inn Image

Pilgrim Inn

Lee
Guest Rating: 6.3/10
(20) reviews
Swimming Pool
  2 Star
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Hilton Garden Inn Lenox/Pittsfield Image

Hilton Garden Inn Lenox/Pittsfield

Pittsfield
Guest Rating: 9.2/10
(4) reviews
Swimming Pool
  3 Star
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Crowne Plaza Pittsfield - Berkshires Image

Crowne Plaza Pittsfield - Berkshires

Pittsfield
Guest Rating: 7.2/10
(70) reviews
Swimming Pool
  3 and 1/2 Star
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Themes: Business-Friendly, Family-Friendly

WyndhamVR Bentley Brook Image

WyndhamVR Bentley Brook

Lanesboro
Guest Rating: 8.2/10
(7) reviews
Swimming Pool
  3 Star
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Jiminy Peak Mountain Resort Image

Jiminy Peak Mountain Resort

Lanesboro
Guest Rating: 8.9/10
(11) reviews
Swimming Pool
  2 Star
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Themes: Family-Friendly

Freebies Available
Hampton Inn & Suites Berkshires-Lenox Image

Hampton Inn & Suites Berkshires-Lenox

Lenox
Guest Rating: 9.2/10
(20) reviews
Swimming Pool
  2 and 1/2 Star
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Themes: Family-Friendly, Business-Friendly

Conroy's B&B Image

Conroy's B&B

Stockbridge
Guest Rating: 10.0/10
(2) reviews
Swimming Pool
  3 Star
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Freebies Available
Berkshire Mountain Lodge Image

Berkshire Mountain Lodge

Pittsfield
Guest Rating: 9.7/10
(3) reviews
Swimming Pool
  3 Star
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Freebies Available
The Red Lion Inn Image

The Red Lion Inn

Stockbridge
Guest Rating: 8.7/10
(28) reviews
Swimming Pool
  3 Star
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Themes: Romantic

The Inn at Stockbridge Image

The Inn at Stockbridge

Stockbridge
Guest Rating: 10.0/10
(1) review
Swimming Pool
  3 Star
prices from
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Freebies Available


97 Pittsfield Hotels
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