
Vacation rentals with a pool in Chatham
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Chatham

Total vacation rentals
Explore 40 vacation rentals in Chatham

Nightly prices starting at
Chatham vacation rentals start at R 5,689 ZAR per night before taxes and fees

Verified guest reviews
Over 580 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Chatham vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Chatham rentals

4.9 Average rating
Chatham stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated rentals with a pool in Chatham
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

ShoestringBayHouse, waterfront & pool in Cotuit
Why the new pricing: airbnb has changed the fee structure to the "host pays" model. The host now pays 100% of the airbnb fees. Welcome to ShoestringBayHouse in Cotuit, waterfront on Popponesset Bay. It's all about the views. Our home overlooks the pool, beach and bay. We include: 2-Bikes, 2-Kayaks, and a Barnstable beach pass with beach chairs. Pet friendly and spacious with 4 BR/ 4.5 baths is priced for six adult guests plus children. Pool: May 15th through mid-October (not heated)
4.97 out of 5 average rating, 32 reviews
Ocean Edge Resort/Pool access/2bedroom-2bath Condo
Recently renovated end unit townhouse located in the heart of The OE Villages. Beautiful views towards the golf course, and southern exposure with lots of natural light, A/C, W/D and private patio with Weber grill and outdoor furniture. Sports Membership so Guest passes are available for purchase at Linx for use of pools, hot tubs and gyms. Additional costs for use of courts may apply. Bike rail trail, Ice cream store, great restaurants, coffee, beaches and Kayak/Bike rentals are all close by.
5.0 out of 5 average rating, 104 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 6/20-9/15/26. The reviews tell all!
4.96 out of 5 average rating, 145 reviews
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
5.0 out of 5 average rating, 112 reviews
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, AC, enjoyable year-round. Vast serene private 1.5 acres adjacent to conservation land. Pool heated Memorial day weekend- last Sunday of 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.
4.98 out of 5 average rating, 54 reviews
Winslow Acres [heated] Pool Escape; pool May-Oct
Pool Closes 10/14/25; reopens mid-may for 2026 season. Hot tub open year-round Escape to the Cape at this beautifully maintained home with lovely seasonal heated pool (heated spring/fall). Hot tub available all year. 4 bedrooms, 2.5 baths (2 showers) plus an outside shower May through October. Plenty of room for up to 8 people (plus pets - fee applies) - sorry, no parties! Only 3 miles to beaches. The ferry to Nantucket and Martha's Vineyard is not far, and a great addition to any Cape trip!
4.92 out of 5 average rating, 53 reviews
Perfect Farmhouse Discounted for Draft Day!
Old Red Farm Inn invites you to forget your worries in this charming space that has everything to offer. Originally built in 1700’s, this updated Inn can be your sanctuary! A perfect fall getaway! A lagoon pool on site, a golf course across the street, walking distance to Little Harbor Beach, and acres of conservation land for hiking provides everything you need in order to relax. This home is over 5,000 ft. and can fit multiple families that are looking for a fun getaway.
4.89 out of 5 average rating, 101 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. 3 night Thursday to Sunday minimum in June.
5.0 out of 5 average rating, 43 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.
4.89 out of 5 average rating, 110 reviews
7-BR Retreat: Pool, Hot Tub, Sauna, Barn
Experience the ultimate getaway at this stunning 7-bedroom retreat, just a mile from Cape Cod’s pristine beaches. Enjoy a top-rated gourmet kitchen, a charming renovated barn, and a Cantina Pool Bar perfect for poolside relaxation. With a sparkling pool and a soothing sauna, this home offers the perfect blend of elegance and comfort. This property is ideal for family vacations, group getaways, and special celebrations. Book now No events allowed.
4.95 out of 5 average rating, 80 reviews
New Seabury Cape Condo | Pool & Beach Escape
Top 5% of Air Bnbs! 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.
4.97 out of 5 average rating, 183 reviews
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.
4.87 out of 5 average rating, 125 reviewsPopular amenities for Chatham rentals with a pool
House rentals with a pool

Ocean Side, Amazing View, close to town/beach, Spa
4.89 out of 5 average rating, 334 reviews
Heated Pool | 5 Min Walk to Beach | Dog-Friendly
5.0 out of 5 average rating, 7 reviews
In-Ground Pool Oasis | 5 Min to Cape Cod Beaches!
4.8 out of 5 average rating, 49 reviews
Unique Hyannis house w pool, playground basketball
5.0 out of 5 average rating, 3 reviews
Coastal Charm New Seabury: 5BRs with Private Pool
4.94 out of 5 average rating, 53 reviews
Hyannis Port Coastal Escape – Pool & Walk to Beach
5.0 out of 5 average rating, 38 reviews
Luxury retreat, in-ground pool, 10-person hot tub
5.0 out of 5 average rating, 42 reviews
Family Cape Cod Oasis-Pool-Hot Tub-Game&Kids Room
5.0 out of 5 average rating, 30 reviewsCondo rentals with a pool

Sea Salt Studio - Steps to Glendon Rd Beach
4.93 out of 5 average rating, 134 reviews
Bright Cape Condo in Ocean Edge
4.92 out of 5 average rating, 25 reviews
Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access
4.96 out of 5 average rating, 99 reviews
Resort Pools & Golf Views · Walk to Bay Beaches
4.87 out of 5 average rating, 76 reviews
Mid Cape Cod, 3 Season Haven by Bass River
4.86 out of 5 average rating, 65 reviews
InnSeason Resorts Captains Quarter's
5.0 out of 5 average rating, 6 reviews
Hidden Hideaway
4.88 out of 5 average rating, 72 reviews
Steps from Bass River Marina · Private Balcony
4.96 out of 5 average rating, 83 reviewsOther vacation rentals with a pool

Townhouse at Ocean Edge 2B/2B + Loft
5.0 out of 5 average rating, 37 reviews
Ocean Edge Townhouse/Pool Access
4.87 out of 5 average rating, 45 reviews
Game Room- Movie Projector Room- Fire Pit
5.0 out of 5 average rating, 12 reviews
Renovated ranch with pool access
4.98 out of 5 average rating, 42 reviews
Waterfront Home w/Dock, Deck, Central A/C & Kayaks
5.0 out of 5 average rating, 29 reviews
Cottage at the Escape Inn
4.97 out of 5 average rating, 36 reviews
Spacious Retreat With Pool, Game Room & Fireplace
4.75 out of 5 average rating, 79 reviews
Beach house in Hyannis with pool
4.89 out of 5 average rating, 9 reviewsDestinations to explore
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