
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 $491 CAD 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 and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Chatham vacation rentals include wifi 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.

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!

Beach Pass Included! Brand New Spa! Central AC!
Welcome to your Italian Villa in the center of Cape Cod! My father, Sal, created this property to make memories that will last a lifetime. What could be better than a secluded yard that feels like a hidden oasis, but is also walking distance or a short drive to tourism? Walk 0.2mi to ice cream and mini golf. Or, drive 10 mins to local beaches, Hyannis Main Street, island ferries, fishing excursions, whale watching, The Cape Cod Melody Tent, the mall, rt 6, Cape Cod Gateway Airport, and more!

Family Sandwich Coastal RetreatPool/firepit
Welcome to your perfect Cape Cod getaway in beautiful East Sandwich! This spacious 4-bedroom, 2.5-bath home was designed for relaxing vacations, family gatherings, and unforgettable summer memories. Enjoy the best of indoor and outdoor living with a private outdoor pool, cozy fire pit area, and comfortable spaces throughout the home for everyone to unwind after a day at the beach. Inside, the home offers bright and welcoming living areas, a fully equipped kitchen, and a spacious dining area.

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!

In-Ground Pool Oasis | 5 Min to Cape Cod Beaches!
Stunning in-ground pool HEATED in May, June, Sept, Oct only. Pool is opened in May! 5 minutes from Craigville, Dowses and Covell's Beach! Perfect for mid-size groups or families, this home sleeps 8 and boasts a dreamy, private, fenced-in backyard w/ a, pool house w/ TV & bar, outdoor shower, and cozy patios. Complete w/ all your beach essentials. We're 13 minutes from Mashpee Commons and 10 minutes from local grocery stores, local bakeries& restaurants. Central to all the Cape has to offer!

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.

Cape Cod Oasis: pool, hot tub, firepit & grill!
Over 4500 sqft of living space in the heart of Cape Cod, with an inviting pool, a hot tub, magnificent garden and expansive outdoor living space big enough to fit your entire party. Welcome to your own private resort! This beautiful custom-built center entrance colonial has room to roam, both inside and out. 5 beds, 5 baths, eco pool, The building is surrounded by lush landscape and tastefully decorated. Fully equipped chef's kitchen. Short drive to the beach!

Wellfleet~Beautiful One Day Perfect The Next
Are you looking for the perfect getaway in charming Wellfleet? This two-bedroom cottage is located in a private, detached cottage village. Enjoy the beautiful SEASONAL in-ground pool (OPENS July 4th & CLOSES LABOR DAY) and a welcoming family-friendly atmosphere. The cottage is centrally located with a five-minute drive to both bay and ocean side beaches, freshwater kettle ponds, Wellfleet center, and the rail trail!

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.

Waterfront Bass River Jolly Captain
Not only will you enjoy your stay surrounded by waterfront views from two floors of living space, you’ll be centrally-located to dining, shopping, nightlife, outdoor activities, on-site heated pool, but you’ll be staying next to a Cape Cod landmark! The iconic Lighthouse with the Jolly Captain perched above, has been welcoming visitors over the Bass River Bridge since 1960!

Jolly Captain Lighthouse
Ever wanted to stay in a lighthouse?! Well this your opportunity. The Jolly captain lighthouse was originally built in 1960 and recently renovated in 2024-2025. Including breathtaking views of Bass River. Access to community pool is available. In addition, dock slip is available for additional cost. Please contact host privately for additional information.
Popular amenities for Chatham rentals with a pool
House rentals with a pool

Renovated Cape Oasis W/ New Pool and Game Room!

Beach house in Hyannis with pool

Fenced Pool, Fire pit, Outside dining, Coffee bar

Mansion with Heated Pool Near Ocean

Modern Cape, Private Heated Pool, Beach, Golf

Spacious Retreat With Pool, Game Room & Fireplace

Heated Pool | Waterfront | A/C | Kayaks | 3 Acres

Relaxing Cape Home <3mi-beach
Condo rentals with a pool

1BR 2nd Floor Condo with pool

Resort Pools & Golf Views · Walk to Bay Beaches

Ocean Edge 2 Bed 2 Bath, Golf & Free Resort Access

Hidden Hideaway

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

Mid Cape Cod, 3 Season Haven by Bass River

Ocean Edge Resort/Pool access/2bedroom-2bath Condo

Steps from Bass River Marina · Private Balcony
Other vacation rentals with a pool

4 King Beds + Heated Pool+Game room+ Putting Green

Popponesset, Exclusive, 3-Bdrm, 4-Bths, Sleeps 6,

Game Room- Movie Projector Room- Fire Pit

Coastal Retreat in East Sandwich - Dogs OK!

Hyannis Port Coastal Escape – Pool & Walk to Beach

The Plymouth Pool House

Family Cape Cod Oasis-Pool-Hot Tub-Game&Kids Room

The Captain's Quarters Suite - #10
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