Part of the New England region in the United States, Massachusetts welcomes travelers looking for adventure and new experiences. It offers a combination of old and new, with attractions such as Freedom Trail in Boston, Old Sturbridge Village, Harvard University in Cambridge, and the vibrant Faneuil Hall Marketplace. Martha’s Vineyard and Cape Cod are the perfect destinations for nature lovers. Travelers can enjoy the white sand, pristine beaches, and rolling mountain views during the summer. Meanwhile, they can see the reveal of fall foliage during autumn. If you’re planning a summer vacation in the state, why not stay at a hotel where you can plunge and relax in the pool with views of the skies? Scroll down and choose from the list of top hotels with outdoor pool in Massachusetts, USA.
We handpicked these listings carefully, considering (wherever possible) recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to outdoor pool. The image galleries get refreshed with the latest updates regularly. They were last updated on October 25, 2025.
1. Harbor Hotel Provincetown (from USD 182)
Welcome to Harbor Hotel, a retro-chic accommodation. The property features an enormous outdoor pool with a poolside bar. Additionally, its rooms are well furnished with amenities and views of the bay. If you are bringing your fur babies, worry not because the hotel offers pet-friendly rooms.
Located by the beach, the hotel gives views of the sunrise and sunset. Activities you may enjoy during your stay here include dolphin watching with Dolphin Fleet, visiting Pilgrim Monument and Provincetown Museum, and checking out Fine Arts Work Center.
Harbor Hotel Provincetown This is a Proud Certified property where you can be extra sure of a welcoming stay.
Address: 698 Commercial Street
68.89 km (42.9 mi) from Pond Meadow Park
2. Club Wyndham Bentley Brook, Hancock (from USD 87)
Limited dining options on-site, but well-stocked kitchens in the suites provide convenience.
Great value for spacious, well-equipped suites in a prime location.
Convenient access to ski resorts and natural attractions in the Berkshire mountains.
Abundance of family-friendly activities, pools, and a game room.
Enjoy a spectacular holiday at this superb hotel situated in the middle of the woodlands. The property offers a wide option of activities guests can enjoy. Aside from the outdoor pool, which features mountain views, they have a sauna, a fitness gym, rustic restaurants and cafes, a game room, and a movie room. You can also play a game of tennis, make use of barbecue facilities, and go hiking.
Take in the views of the mountain every morning from their very well-appointed suites, which feature a balcony. Each room is equipped with a comfy bed, a bathroom with toiletries, a full kitchen with a dining area, a living room with cable TV, and free Wi-Fi.
Club Wyndham Bentley Brook
Address: 1 Corey Road
194.28 km (120.8 mi) from Pond Meadow Park
3. The Escape Inn, South Yarmouth (from USD 152)
This homey hotel located in South Yarmouth is the perfect home base for exploring the wonders of Cape Cod. Featuring a large outdoor swimming pool surrounded by sun loungers, the property offers a relaxing experience. They also offer accommodation that is carefully curated with comfort in mind. Each room is accented with a colorful palette grounded by hardwood floors. Amenities include a comfy bed, a sitting area, an en-suite bathroom, a cable TV, and Wi-Fi connection. You can stuff yourself with continental breakfast every morning.
What’s more, you’ll have easy access to a number of beaches, attractions, and golf courses. You can also experience a water adventure with “Jeromin,” a sailboat.
The Escape Inn
Address: 1237 Route 28 PO Box 1054
88.29 km (54.9 mi) from Pond Meadow Park
4. Aiden by Best Western @ Cape Point, West Yarmouth (from USD 135)
Delight yourself with a luxurious stay by booking a room at this hotel situated in West Yarmouth. With attractions and recreational activities nearby, such as John F. Kennedy Hyannis Museum, Hy-Line Harbor Cruise, Grays Beach Boardwalk, and more, this place allows you to explore Cape Cod with ease.
After a day of fun and adventure, rest your weary body in one of the properties’ elegant rooms that is fitted with comfy beds, a sitting area, coffee-making facilities, a flat-screen TV, and a bathroom. Other hotel amenities you may enjoy are a seasonal outdoor pool and a year-round indoor pool, a fitness gym, a relaxing lounge, and an on-site restaurant.
Aiden by Best Western Cape Cod - West Yarmouth
Address: 476 Route 28, West Yarmouth, West Yarmouth (MA), United States, 02673-4841
86.72 km (53.9 mi) from Pond Meadow Park
5. Fairfield Inn by Marriott Amesbury (from USD 170)
Varied and ample breakfast options, including hot and cold foods, though crowded at peak times, with friendly kitchen staff, and nearby dining recommendations from the hotel staff
Reasonable pricing for the area, consistent with similar properties
Convenient, easy-to-find location near the highway, close to Newburyport and Plum Island, safe and quiet area with nearby entertainment and shopping options
Clean, comfortable rooms with hot showers, friendly and accommodating staff, convenient location near attractions and restaurants, pool on site, easy drive to nearby coastal areas
Excellent comfort and convenience await you at Fairfield Inn by Marriott Amesbury. This Marriott property features a seasonal outdoor pool, where you can relax, and well-furnished rooms with modern amenities, such as comfy beds, a bathroom with toiletries, a workspace, a satellite TV, a coffee maker, a mini-refrigerator, and a microwave. A hearty breakfast is served every morning at the dining area.
Visit nearby attractions, such as historic Lowell’s Boat Shop, Amesbury Sports Park, the market square, and Newburyport Waterfront Park, where you can gaze upon the sunset.
Fairfield Inn by Marriott Amesbury
Address: 35 Clarks Road
71.1 km (44.2 mi) from Pond Meadow Park
6. Doubletree by Hilton Boston - Rockland (from USD 138)
Expect a seamless stay and a refreshing time at Doubletree by Hilton Boston - Rockland. Its rooms are designed with light colors that give your stay a luxurious vibe. Each room features comfy beds, a private bathroom, a sitting area, a work desk, a coffee maker, an LCD TV, and access to Wi-Fi.
Unwind in their outdoor pool or enjoy happy hour at Conrad’s Bar and Grill, which features traditional American cuisine. The fitness gym is open 24 hours, so you can work out any time of the day.
DoubleTree by Hilton Boston-Rockland
Address: 929 Hingham Street
7.87 km (4.9 mi) from Pond Meadow Park
7. Homewood Suites by Hilton Boston / Andover (from USD 179)
A stay at this cozy hotel allows you to enjoy a dip in the outdoor pool while being surrounded by trees. When you want to rest, choose from among the hotel’s 82 guest rooms, each featuring a king and queen-sized bed, a bathroom, a living room with HDTV, a work desk, a kitchenette, and a separate dining area. You will also have free access to Wi-Fi to keep you connected.
This hotel also has a great location close to local attractions and other cities in the New England region.
Homewood Suites by Hilton Boston/Andover
Address: 4 Riverside Drive
56.99 km (35.5 mi) from Pond Meadow Park
8. Sandwich Lodge and Resort (from USD 129)
There will never be a dull moment when you stay at this spectacular hotel situated in Sandwich. The property offers amenities and activities that guests can enjoy. Swim and relax in their seasonal outdoor pool or heated indoor pool, which features a hot tub. Play with your family or friends at the arcade room and indoor ping pong table. Outdoor activities they offer on site include volleyball, shuffleboard, horseshoes, and a barbecue area with grills and picnic tables. Choose from their 75 comfortable rooms and suites to tuck in for the night.
Enjoy easy access to stunning beaches, restaurants, cafes, shops, and museums, such as Sandwich Glass Museum and Heritage Museums and Gardens.
Sandwich Lodge & Resort
Address: 54 Route 6A
62.29 km (38.8 mi) from Pond Meadow Park
9. The Colonnade Hotel, Boston (from USD 805)
Luxurious accommodation is offered at this lavish hotel, which features a seasonal rooftop outdoor pool. Rooms in The Colonnade Hotel are equipped with amenities, such as beds with premium linen, clean bathrooms, an LCD TV, a mini-refrigerator, a coffee maker, a dedicated workspace with city vistas, and Wi-Fi access. Its interior is primarily monochrome with nude accents. Satisfy your cravings at the on-site restaurant and stay fit at the gym.
The property is strategically located close to the city’s industrial hubs and attractions, such as Symphony Hall, Prudential Tower, Boston Public Library, Boston Museum of Fine Arts, and more.
The Colonnade Hotel This is a Proud Certified property where you can be extra sure of a welcoming stay.
Address: 120 Huntington Avenue
17.8 km (11.1 mi) from Pond Meadow Park
Savor the best of Massachusetts
The perfect destination for a summer vacation, this state in New England has a lot in store for you. It offers a variety of adventures that will keep you entertained. While you’re here, enjoy staying in any of its top hotels with outdoor pools.
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