Find Hotels with a Pool in Winchester, MA

Seaport Hotel Boston: Hotel, 9-minute walk from Boston Convention and Exhibition Center. Features 2 restaurants, an indoor pool, and a health club. Omni Boston Hotel at the Seaport: Hotel, 3-minute walk from Boston Convention and Exhibition Center. Offers 2 bars, a pool, and a snack bar/deli. Hilton Boston Park Plaza: Hotel located near Boston College. Offers 2 restaurants, an indoor pool, and complimentary wireless internet access. The Dagny Boston: Hotel, 2-minute walk from Boston Convention and Exhibition Center. Offers a snack bar/deli, an indoor pool, and complimentary wired internet access.

While you’re in the area, consider exploring places like TD Garden, Fenway Park, and New England Aquarium. Make a point to visit attractions like Middlesex Fells Reservation and Winter Pond.

You may want to consider an accommodation that has an outdoor pool if you will be visiting Winchester in the hottest months of July, August, or June when the average temperature is 69°F. Lodging with an indoor pool may be what you want if you come to town during the coldest months of January, February, or December when the average temp is 33°F.

Knowing the transportation options in Winchester can help you enjoy the area beyond your hotel pool. To explore the surrounding area, hop aboard a train at Winchester Station or Winchester Wedgemere Station. Winchester might not have many public transit options to choose from so consider a car rental to maximize your time.