Hotels with a swimming pool near The Berkshires,

Enjoy a family-friendly resort with indoor and outdoor pools, fitness center, and stunning views in the Berkshires.

Lodge with indoor pool, hot tub, and picnic area near golf course and Tanglewood Music Center in Pittsfield.

Family-friendly hotel with seasonal outdoor pool, arcade, and dining options near Housatonic River in Lee, Massachusetts.

Enjoy an indoor pool, hot tub, and fitness center at this hotel in the heart of North Adams, steps from local attractions.

Enjoy a health club and indoor pool at this centrally located hotel in Pittsfield, close to local attractions.

Ski-in/ski-out resort with 2 hot tubs, multiple dining options, and family-friendly amenities in Hancock, Massachusetts.

Historic hotel with outdoor pool, three restaurants, and a fitness center in Stockbridge's charming district.

Enjoy a seasonal outdoor pool and free Wi-Fi in this centrally located motel in Pittsfield, Massachusetts.

Enjoy an outdoor pool and garden at this motel, conveniently located near Guido's Marketplace in Lenox.

Enjoy an indoor pool, complimentary breakfast, and a fitness center at this hotel near Housatonic River in Great Barrington.

Enjoy a stay with an indoor pool, complimentary breakfast, and a fitness center in the heart of Great Barrington.

Hotel with indoor pool, fitness center, and on-site dining in a convenient location near Guido's Marketplace.

Enjoy an indoor pool and fitness center at this hotel in Lenox, just minutes from Kennedy Park and The Mount.

Enjoy an indoor pool, hot tub, and fitness center at this hotel in Williamstown, just a short walk from Colonial Plaza.

Enjoy a stay with an indoor pool, hot tub, and complimentary breakfast in Pittsfield, Massachusetts.

Enjoy a seasonal outdoor pool and complimentary breakfast at this cozy motel in Williamstown's historical district.

Relax in a spacious inn featuring an outdoor pool, hot tub, sauna, and complimentary breakfast in North Adams.