
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.

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
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
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!
4.93 out of 5 average rating, 224 reviews
Unique Hyannis house w pool, playground basketball
Book this one-of-a-kind private resort-style home and make unforgettable memories with family and friends! Enjoy a heated pool (from May 23-26 till Oct 1), basketball court, playground, and full privacy—fenced-in and surrounded by mature trees. Spacious 4BR/2.5BA, perfectly tucked away from the street and yet just minutes to Main Street, shops and restaurants, 15 min walk to Hyannis Harbor and ferries to islands, 5 min drive to beaches. Relax, play, and reconnect in your own Cape Cod oasis!
5.0 out of 5 average rating, 3 reviews
Heated Pool | 5 Min Walk to Beach | Dog-Friendly
Relax at this charming South Yarmouth retreat featuring an electric-heated saltwater swimming pool and a prime walkable location to the beach. Perfect for families or couples, this spacious home offers modern comforts, a fully equipped kitchen, seven beds, and a peaceful yard. Air Conditioners throughout the home. Dog-friendly, so your furry companion can join the fun! Enjoy the best of Cape Cod with dining, shops, and attractions just minutes away! 23W - Hosted by Tuxfin Hospitality
5.0 out of 5 average rating, 7 reviews
Townhouse at Ocean Edge 2B/2B + Loft
Experience resort-style living at its finest! Tucked away just a 10-minute drive to the beach, this delightful townhouse offers the perfect blend of comfort and convenience. With two bedrooms, two baths, and an additional cozy loft space, there's ample room for relaxation. Enjoy lounging on the patio, take a refreshing dip in one of the resort pools (for an additional fee paid directly to Ocean Edge) or head to the beach for some sun and surf. Your ultimate getaway awaits!
5.0 out of 5 average rating, 37 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, 44 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
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!
4.94 out of 5 average rating, 53 reviews
Seaview Summit | Ocean Views, Indoor Pool, Beach
Perched above the coastline with panoramic Atlantic views, Seaview Summit House is Plymouth's premier oceanfront retreat. Designed for discerning travelers seeking serenity, space, and sophistication. With a heated indoor pool, expansive outdoor living areas, and direct beach access just moments away, this stunning property delivers a five-star experience in every season. Book your stay today. You'll be glad you did.
4.89 out of 5 average rating, 179 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

Private Pool, near beaches, 3 BR/3 BA, Central Air
4.96 out of 5 average rating, 145 reviews
Lovely villa w pool/hottub, central AC, near beach
5.0 out of 5 average rating, 15 reviews
In-Ground Pool Oasis | 5 Min to Cape Cod Beaches!
4.8 out of 5 average rating, 49 reviews
Resort Home, Heated Pool, Putting Green, Game Room
4.93 out of 5 average rating, 29 reviews
ShoestringBayHouse, waterfront & pool in Cotuit
4.97 out of 5 average rating, 32 reviews
Upscale Secluded Home w/Central AC, Pool & Firepit
4.94 out of 5 average rating, 16 reviews
Family Cape Cod Oasis-Pool-Hot Tub-Game&Kids Room
5.0 out of 5 average rating, 30 reviews
Luxury retreat, in-ground pool, 10-person hot tub
5.0 out of 5 average rating, 42 reviewsCondo rentals with a pool

Sea Salt Studio - Steps to Glendon Rd Beach
4.93 out of 5 average rating, 134 reviews
Ocean Edge Resort-Pool Access-CentralAC-2 bdr/2bth
5.0 out of 5 average rating, 112 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
InnSeason Resorts Captains Quarter's
5.0 out of 5 average rating, 6 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
Steps from Bass River Marina · Private Balcony
4.96 out of 5 average rating, 83 reviewsOther vacation rentals with a pool

Ocean Edge Townhouse/Pool Access
4.87 out of 5 average rating, 45 reviews
The Captain's Quarters Suite - #10
4.97 out of 5 average rating, 78 reviews
Cottage at the Escape Inn
4.97 out of 5 average rating, 37 reviews
Wellfleet~Beautiful One Day Perfect The Next
4.87 out of 5 average rating, 67 reviews
Renovated Cape Oasis W/ New Pool and Game Room!
4.94 out of 5 average rating, 33 reviews
Renovated ranch with pool access
4.98 out of 5 average rating, 42 reviews
Game Room- Movie Projector Room- Fire Pit
5.0 out of 5 average rating, 12 reviews
Family friendly luxury home with heated pool & spa
4.8 out of 5 average rating, 5 reviewsDestinations to explore
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