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 5,755 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.

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Top guest favorite

Guest suite in Centerville

“The Hideaway”Private Guest Suite/Pool/Beach Pass

Enjoy a bit of Cape Cod in a friendly and walkable neighborhood of lush green trees , flower gardens, and a walking trail. Less than 1 mile from Centerville's shops and restaurants. Less than 2 miles from Craigville Beach and its beachside walk up shanty’s for lunch. A small beach on Lake Wequaquet is only 2 miles down the road . Main street Hyannis, a walkable downtown with many shops and restaurants is a quick 10-minute drive. Ocean marinas, and ferries to the islands, are a 15 minute drive.

ValueFamilyAccuracy

4.99 out of 5 average rating, 105 reviews

Top guest favorite

A spacious backyard is featured, highlighting a refreshing oval pool surrounded by a textured patio. Lounge chairs are positioned for relaxation under the sun. Lush greenery and trees provide a natural border, while a well-kept lawn enhances the inviting outdoor space.

Home 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!

LocationFamilyQuiet

5.0 out of 5 average rating, 15 reviews

Top guest favorite

A sunny outdoor area is showcased, featuring a private heated pool surrounded by lounge chairs. Large blue umbrellas provide shade next to the pool, while decorative landscaping and a wooden playset are visible in the background. The space invites relaxation and comfort.

Home in Harwich

Resort Home, Heated Pool, Putting Green, Game Room

Escape to our serene, spacious home, a private oasis perfect for families & groups! This stylish retreat features a heated pool, putting green, fire pit, and a full game room with a pool table, poker lounge, and arcade games. Nestled in a peaceful, wooded neighborhood with nearby lake access, it's the ultimate blend of relaxation and entertainment. Enjoy a seamless self-check-in experience with an on-site EV charger. You will receive a four-digit access code after you agree and complete the hous

FamilyLocationHospitality

4.93 out of 5 average rating, 29 reviews

Top guest favorite

An open living area features large glass doors that provide views of the golf course. A comfortable seating arrangement includes a recliner and a sectional sofa. A spiral staircase leads to the loft above, and a mounted television is positioned above a modern fireplace.

Condo in Brewster

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.

ValueLocationCleanliness

5.0 out of 5 average rating, 105 reviews

Top guest favorite

The expansive pool, surrounded by a landscaped yard, features a vibrant blue surface reflecting the clear sky. Comfortable lounge chairs are positioned alongside, inviting relaxation. A floating inflatable adds a playful touch to the tranquil setting.

Home in Cotuit

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!

FamilyValueCondition

4.96 out of 5 average rating, 146 reviews

Top guest favorite

Home in Brewster

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.

LocationValueWalkability

4.98 out of 5 average rating, 54 reviews

Superhost

Home in Yarmouth

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

LocationFamilyWalkability

5.0 out of 5 average rating, 7 reviews

Guest favorite

A lagoon-style pool surrounded by a concrete deck provides lounge chairs and shaded areas under umbrellas. A gazebo is visible in the background, complementing the lush greenery that borders the property.

Villa in Wareham

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.

LocationFamilySleep quality

4.89 out of 5 average rating, 101 reviews

Top guest favorite

Bright and airy living space is highlighted by a spiral staircase leading to an open loft. A plush light grey sofa faces a coffee table on a woven area rug, while a dining table and chairs are visible in the background. Modern kitchen cabinetry offers a sleek contrast.

Apartment in Brewster

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!

LocationValueBathroom

5.0 out of 5 average rating, 37 reviews

Top guest favorite

Condo in New Seabury

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.

FamilyValueBathroom

4.97 out of 5 average rating, 184 reviews

Guest favorite

An aerial view of a spacious property featuring a uniquely shaped heated saltwater pool surrounded by a stone patio. A large deck is positioned next to the pool, with several lounge chairs arranged nearby and greenery framing the area.

Home in New Seabury

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!

LocationValueNearby

4.94 out of 5 average rating, 53 reviews

Top guest favorite

The exterior of the Cape Cod cottage is shown, featuring a light-colored siding and a unique turret-like structure. Lush green landscaping surrounds the home, which is set back from a gently curved pathway. Tall trees provide natural shade in the area.

Townhouse in Brewster

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.

LocationValueCheck-in

4.87 out of 5 average rating, 125 reviews