Vacation rentals with a pool in Chatham

Pool. Hot Tub. Game Room. Walk to Beach. Luxury!

Welcome to The Tide Watch - our luxurious retreat, perfect for families or a group of friends! This stunning home features high-end furniture, a pool, hot tub & games including ping pong & air hockey. With kid-friendly amenities, everyone will feel at home. Relax, play & create unforgettable memories in this upscale oasis designed for fun & relaxation! Walk to small neighborhood beach 3 min drive to Jacknife Beach 6 min drive to downtown Chatham Experience Chatham with us & Learn More Below!

4 BD slice of Harwich Heaven

Come to our beautiful, spacious, and comfortable home away from home. Near to many ponds, nature trails, and the Rail Trail bike path. 4 BDs (1 king, 2 queens, 2 twins), 2 1/2 baths, with AC, patio, and in ground pool. Four separate living spaces- cozy living room with large TV, sun filled family room, furnished basement (with entertainment center, perfect for kids & teens), and patio with a pool & BBQ grill- make our place perfect for family gatherings. There's plenty of room to spread out!

Private Pool, near beaches, 3 BR/3 BA, Central Air

Enjoy the Barnstable historic seaside village of Cotuit in this sprawling house with central air, nestled in the pines on a quiet street with private gated (unheated) pool, lg. backyard, firepit, ample parking, just blocks from Main St, Ropes Beach, scenic ocean views, fort playground, and Kettleer baseball. Each bedroom has a TV and ensuite bathroom! Relax in the seasonal sunroom overlooking the pool; grill burgers on the patio. Max. 9 (6 adults). Pool open 6/20-9/15/26. The reviews tell all!

Sea Salt Studio - Steps to Glendon Rd Beach

Funky studio (Unit #1) only 175 yards from a white sand beach on Nantucket Sound. Soak up the sun at the beach, relax by the pool or enjoy a relaxing cocktail on your own private patio. This studio is equipped with a fridge, microwave and gas stove as well as a fully stocked kitchenette and cable/Roku TV. A futon couch offers extra sleeping space, if needed. Outside, enjoy a natural gas grill. Walk or bike to multiple restaurants, ice cream shops and all the amenities Dennis Port has to offer.

Beach Pass Included! Brand New Spa! Central AC!

Welcome to your Italian Villa in the center of Cape Cod! My father, Sal, created this property to make memories that will last a lifetime. What could be better than a secluded yard that feels like a hidden oasis, but is also walking distance or a short drive to tourism? Walk 0.2mi to ice cream and mini golf. Or, drive 10 mins to local beaches, Hyannis Main Street, island ferries, fishing excursions, whale watching, The Cape Cod Melody Tent, the mall, rt 6, Cape Cod Gateway Airport, and more!

The Holly Cottage

Welcome to Centerville, enjoy this fully equipped 1 bedroom 1 bath home with an easy walk or ride to just about everything. Enjoy the nearby ocean and beaches, or take a ride downtown to Main Street for dining and entertainment. Only a short distance to the ferries for a day trip to the islands and you can be back in time to catch a concert at the Melody Tent. Enjoy your days by the pool and your evenings grilling out on the large deck or chatting with the koi fish.

Great Location. Near Beach & Main Street. Unit M1

Our home-away-from-home accommodations include this charming studio with lawn space, a private deck with outdoor furniture and a gas grill. The cottage is comfortably furnished and features a small kitchen. This cottage has a queen bed and a table with sitting area. The kitchen is nicely updated with updated with beautiful granite countertops and stainless steel appliances including an stove/oven, microwave, mini-fridge, toaster, coffee maker. Keurig, and kettle.

Heated Pool | Waterfront | A/C | Kayaks | 3 Acres

Relax at this serene waterfront home on Mill Pond in Yarmouth Port. This spacious 4 bedroom (6 bed), 3 bath retreat offers beautiful water views, a private in-ground heated saltwater pool, sunroom, and expansive outdoor living space with 3 acres of land. Paddle our kayaks from the backyard, enjoy nearby bike paths and walking trails, or unwind just minutes from Cape Cod beaches. Perfect for families or peaceful group getaways. 18C - Hosted by Tuxfin Hospitality

Coastal Charm New Seabury: 5BRs with Private Pool

Welcome to our sunny 5-bedroom New Seabury home! Perfect for families, we offer an open layout, full kitchen, and coffee bar. Relax on the deck, enjoy our fire pit, or swim in our heated saltwater pool (open mid-May to Oct). We’re just 5 mins from South Cape Beach and close to Mashpee Commons and the Popponesset Marketplace. Come make memories in our little slice of Cape Cod paradise! We’d love to host your next getaway!

Renovated Cape Oasis W/ New Pool and Game Room!

10 guests · 4 bedrooms · 7 beds (including pull-out sofas) · 3 bathrooms · Private Pool · Game Room · 1 Mile to Beach Welcome to your perfect Cape Cod escape in Hyannis, MA! Located on a quiet cul-de-sac, this fully renovated vacation home offers the perfect mix of luxury, comfort, and fun. Enjoy a private, resort-like experience just minutes from the beach, Main Street, and all the best of Cape Cod.

Ocean Edge Cape House with Beach, Pool, and AC

Your dream Cape Cod getaway awaits! This classic Cape Cod cottage is nestled in the heart of Brewster, offering a perfect blend of comfort, relaxation, and outdoor adventure. With access to a private beach, resort-style amenities, and iconic local attractions, this is the ultimate retreat for families, couples, or groups looking to experience the best of the Cape.

Jolly Captain Lighthouse

Ever wanted to stay in a lighthouse?! Well this your opportunity. The Jolly captain lighthouse was originally built in 1960 and recently renovated in 2024-2025. Including breathtaking views of Bass River. Access to community pool is available. In addition, dock slip is available for additional cost. Please contact host privately for additional information.