Holiday rentals with a pool in Chatham

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Chatham

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite

Home in Chatham

5 out of 5 average rating, 6 reviews

*NEW* Pool. Hot Tub. Game Room. Beach Nearby!

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!

Top Guest favourite

Home in Cotuit

4.95 out of 5 average rating, 120 reviews

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 6/20-9/15/24. The reviews tell all!

Guest favourite

Condo in Brewster

4.97 out of 5 average rating, 181 reviews

Ocean Edge Resort-Pool Access-End Unit-2 bdr/2 bth

2nd floor Ocean Edge end unit condo located in the heart of Brewster with access to OE resort amenities: pools, gyms, tennis courts, as well as access to resort activities (fees apply). Easy access to Cape Cod Rail Trail for bicycles. Scenic route 6A offers arts & crafts galleries and local shops. A 10 minute car ride to a 36 hole Captains Golf course. Short ride to 10 Brewster bay beaches famous for tidal flats. A 30 minute ride to Cape Cod National Sea Shore. Welcome to your Happy Place!

Top Guest favourite

Home in Oak Bluffs

4.94 out of 5 average rating, 200 reviews

Spectacular beach & pool combo; beautiful sunsets!

Close to airport, you’ll love backyard beach, water view, pool/grass yard, ambiance and outdoors space. Beach & Pool (POOL HEAT STARTS SUMMER, ENDS 9/1) is a hard to find combination!! Location is private, yet it's close to the 3 largest towns on Martha's Vineyard. Great for couples, families (with kids), and big groups. Enjoy dinner with the indoor/outdoor Sonos music system during a beautiful sunset! NOTE; Rate increase in high season, pool/spa is a combined unit & ONLY heated in summer!

Guest favourite

Condo in Dennis Port

4.9 out of 5 average rating, 104 reviews

The Sea Salt Studio - Steps to the Beach!

Gorgeous studio only 175 yards from white sand Glendon Road beach. 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, Bluetooth speaker, and 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.

Guest favourite

Condo in Brewster

4.93 out of 5 average rating, 55 reviews

Stylish Ocean Edge Condo #TheCouplesNest

Experience Cape Cod from our stylish 2nd floor condo in Fletcher Village at Ocean Edge, Brewster. Centrally located, it offers easy access to beaches, the Rail Trail, and local dining. Enjoy amenities like pools, tennis, and golf. The modern condo features a fully equipped kitchen and a balcony, perfect for relaxation or adventure throughout the year. Whether you're biking on scenic trails or relaxing by the pool, our condo provides the ideal setting for a memorable Cape Cod experience.

Guest favourite

Home in Plymouth

4.9 out of 5 average rating, 124 reviews

Seaview Summit | Ocean Views, Indoor Pool, Beach

Welcome to Seaview Summit House, where you can enjoy breathtaking panoramic ocean views, take a dip in our heated swimming pool, and take a short walk to the beach. Our spacious and beautifully decorated home features a large living area with comfortable seating, a fully equipped kitchen with all the essentials, and a dining area that seats everyone. You'll have plenty of room to spread out and enjoy your time together, whether you're lounging inside or soaking up the sun outside.

Guest favourite

Home in Brewster

5 out of 5 average rating, 10 reviews

Cape Cod Oasis: pool, hot tub, firepit & grill!

Over 4500 sqft of living space in the heart of Cape Cod, with an inviting pool, a brand new hot tub, magnificent garden and expansive outdoor living space big enough to fit your entire party. Welcome to your own private resort! This beautiful custom-built center entrance colonial has room to roam, both inside and out. 5 beds, 5 baths, eco pool, The building is surrounded by lush landscape and tastefully decorated. Fully equipped chef's kitchen. Short drive to the beach!

Top Guest favourite

Home in Harwich

5 out of 5 average rating, 23 reviews

Harwich Haven: Pool & Fire Pit

Welcome to The Harwich Haven! This 4-bed, 3.5-bath retreat in Harwich, MA offers a spacious family room, modern kitchen, swimming pool, fire pit, two decks with outdoor dining, an outdoor grill, private fenced in yard, two newly renovated ensuite bathrooms with spa amenities and more. With easy access to beaches, restaurants, and shops, it's your perfect vacation getaway! Saturday to Saturday weekly rentals only July & August. 4 night Thursday to Sunday minimum in June.

Guest favourite

Cottage in Centerville

4.92 out of 5 average rating, 87 reviews

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.

Superhost

Home in Plymouth

4.84 out of 5 average rating, 19 reviews

Mansion with Heated Pool Near Ocean

Welcome to one of Plymouth’s largest vacation homes, offering 4,000 square feet of comfortable living space and a heated pool for summer relaxation. The open floor plan provides plenty of room to unwind, whether you’re enjoying a meal together or lounging by the pool. Perfectly located just minutes from both the ocean and downtown Plymouth, you’ll have easy access to beaches, restaurants, and historic attractions while enjoying a peaceful residential setting.

Top Guest favourite

Home in Yarmouth

4.91 out of 5 average rating, 22 reviews

Room for multiple families!

Bring the whole family or multiple families to this great place with lots of room for a year-round getaway! The pool and outdoor space plus proximity to MULTIPLE beaches plus a nearby freshwater pond make this the perfect summer spot! Access to the rail trail is just down the street for a walk, run or bike. Near lots of outstanding restaurants and shopping you will not have any trouble filling your days with fun any time of year!