Vacation rentals with a pool in Chatham

Ocean Edge Resort-Pool Access-CentralAC-2 bdr/2bth

Modern 2nd floor 2 bed/2 full bath Ocean Edge condo located in the heart of Brewster with balcony overlooking the resort golf course. Access to OE resort amenities (additional fees apply). Easy access to Cape Cod Rail Trail. Scenic route 6A offers arts & crafts galleries, coffee places 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. 15 minute walk to Ellis Landing Beach, great sunsets! Central A/C and heat

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!

Modern Cape, Private Heated Pool, Beach, Golf

Welcome to your perfect vacation/reunion in the center of the Cape. Min. to 3 golf courses, 5 ocean beaches, lakes, park, trails. Bright modern quality home available year-round. Vast serene private 1.5 acres adjacent to conservation land. Lighted Private heated saltwater pool Mid May to End Sept. Bocce Court, Putting green, Corn hole, Hammock, Outdoor shower, AC. Expansive double deck with awning. Beautiful indoor/outdoor dining/entertaining. All essentials provided. 7+ free parking.

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.

5-bedroom Cape with a pool and yard games.

Five-bedroom and three-bath Cape style home with large fenced backyard and an inground pool. Various yard games are available - outdoor ping pong table and corn toss. Short distance to Pleasant Bay, freshwater ponds, and the ocean. Approximately five miles from downtown Chatham and Orleans Center. A variety of local shops, and restaurants, and catch the Cape Cod Baseball under the lights just minutes away. (Our pool is not heated - the opening and closing is weather dependent).

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. 3 night Thursday to Sunday minimum in June.

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.

The Port - #5

Come and stay at this classic cape cod oasis directly across the street from Allan Harbor. Tucked in a quiet, family friendly neighborhood. This space has a private entrance with a table for 2, where you can sit, relax and enjoy the fresh air off the comfort of your room. Enjoy easy access to popular shops, restaurants, beaches and a ferry to Nantucket from this cozy getaway. Easy self check in with free parking for 1 car. *Pack n' Play upon request

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.