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!

CapeSearenity-Large Pool-Beach Passes-Family Fun!

Visit Cape SeaRenity–a stunning home w/solar heated pool and outdoor lounge, perfect for a memorable family vacation and a fabulous Cape Cod experience. Escape to Cape SeaRenity—a beautifully updated home near Barnstable Village with a pool, outdoor lounge, & stylish interiors. Minutes from beaches, shops, dining, & whale-watching. Enjoy a modern kitchen, game-filled garage, bikes & kayaks. With thoughtful design & ProHost® support, it’s the perfect base for exploring Cape Cod with your family.

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!

Rock on Wellfleet!

A wonderful Wellfleet location! This second floor rental has a spacious bedroom with a queen bed, bathroom with a tub and living area with a well stocked kitchen. You would have the whole upstairs to yourself with a private door to come and go. You are also invited to use our pool at anytime! We're located very close to the Cape Cod Rail Trail for miles of bike riding, PB Boulangerie Bistro, Marconi Beach, the iconic Wellfleet drive-in and so much more. Bedding, towels and essentials provided.

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.

Studio Apartment

Private Studio Apt on lower level of owner occupied House.Private deck overlooking Pond. Queen bed, single sofabed/and small sleeping loft. Very comfortable for 2 people but can sleep up to 4. Kitchenette w/dinnerware and cookware. Coffee maker, fridge, microwave, toaster oven, outside gas grill. Private bath/shower. TV, WiFi, A/C. Pond access, SUP, kayaks. Pool/hot tub on Main House level available for use on request. Sunrise view. Golfcourses, shopping, restaurants, beaches nearby.

Upscale Secluded Home w/Central AC, Pool & Firepit

Experience the charm of Centerville, a quaint village on Cape Cod! This property is 1.7 acres with beautiful coastal scenery. Centerville offers a peaceful vibe loved by visitors and locals. Enjoy the serene Centerville Lakes or our stunning Saltwater Private Pool! 5 mins to Craigville Beach 5 mins to Wequaquet Lake Boat Ramp- one of Centerville’s largest and most scenic lakes. 8 mins to downtown Osterville 10 mins to Ferry to Nantucket and MV 10 mins from Hyannis Airport

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.

Historic 1 Bed/In Town/Best Location/Hot tub/deck

Please do not book weekends, holidays, or summer dates in advance. This 1-bedroom is only offered to fill midweek gaps when the full home isn’t booked. Beautifully restored historic home in the heart of town—steps from the Pilgrims' first settlement, ocean, restaurants, shops, and more. Located on Town Brook near the Gristmill, with a deck, firepit, hot tub, grill, cozy bed, and working wood stove. Clean, comfortable, and full of charm.

New Seabury Cape Condo | Pool & Beach Escape

Welcome to your coastal getaway at The Mews in New Seabury, Mashpee—a refined Cape-style condo tucked within an intimate golf course community. This exclusive enclave of just 15 residences offers a peaceful, private escape with access to a shared association pool reserved solely for residents. Enjoy nearby beaches like South Cape Beach State Park and Mashpee Town Beach, both just minutes away, for the perfect Cape Cod retreat.