Hotels with a swimming pool in Stockbridge

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

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

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.

Adults-only bed and breakfast with outdoor pool, garden views, and complimentary cooked-to-order breakfast in Lenox.

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

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

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

Enjoy a refreshing stay with an outdoor pool and complimentary breakfast in Austerlitz, New York.

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

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