Vacation rentals with a pool in Chatham
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Chatham
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chatham rentals with a pool
House rentals with a pool
Home in Orleans
4.88 out of 5 average rating, 17 reviews5-bedroom Cape with a pool and yard games.
Jun 1 – 8
Home in Dennis
4.89 out of 5 average rating, 28 reviewsWalk to the beach or sit poolside! Updated studio!
Apr 4 – 11
Home in Falmouth
5.0 out of 5 average rating, 26 reviewsCheerful residential home with swimming pool
Jun 7 – 14
Home in Eastham
5.0 out of 5 average rating, 9 reviewsModern Beach House w/ Heated Pool & Game Room!
Mar 19 – 26
Home in Eastham
5.0 out of 5 average rating, 6 reviewsLovely villa w pool/hottub, central AC, near beach
Sep 30 – Oct 7
Home in North Truro
4.93 out of 5 average rating, 98 reviewsHeated Pool, Beach, Pets, ADA, 5 bath, EV Charge
Jan 7 – 14
Home in Cotuit
4.91 out of 5 average rating, 11 reviewsShoestringBayHouse, waterfront & pool in Cotuit
Dec 4 – 11
Home in Sandwich
4.99 out of 5 average rating, 69 reviews"Cape Escape" luxury home w/pool & beach access.
Nov 1 – 8
Condo rentals with a pool
Condo in Yarmouth
5.0 out of 5 average rating, 5 reviewsCarolyn's Bass River Condo
Oct 10 – 17
Condo in Brewster
4.88 out of 5 average rating, 24 reviewsStylish Ocean Edge Condo #TheCouplesNest
Nov 8 – 15
Condo in Dennis
4.9 out of 5 average rating, 71 reviewsThe Sea Salt Studio - Steps to the Beach!
Sep 15 – 22
Condo in Dennis
4.83 out of 5 average rating, 18 reviews1BR 2nd Floor Condo with pool
May 9 – 16
Condo in Brewster
4.97 out of 5 average rating, 39 reviewsOcean Edge 2 Bed 2 Bath, Golf & Resort Free Access
Nov 6 – 13
Condo in Brewster
4.83 out of 5 average rating, 18 reviewsOcean Edge: 2 bed/2 bath - Pool/Gym, Near Beaches
Jun 5 – 12
Condo in Brewster
5.0 out of 5 average rating, 52 reviewsOcean Edge Resort/Pool access/2bedroom-2bath Condo
Jan 18 – 25
Condo in Dennis
4.83 out of 5 average rating, 65 reviewsComfy Cape Escape! Spacious, Cozy, Close to Beach!
Dec 1 – 8
Quick stats about vacation rentals with a pool in Chatham
Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
200 reviews
Nightly prices starting at
G$47,986 GYD before taxes and fees
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