Holiday 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.
Holiday 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 Sagamore Beach
4.91 out of 5 average rating, 146 reviewsSpacious Upper Cape Retreat with Private Pool
30 Jan – 6 Feb
Home in Dennis
4.88 out of 5 average rating, 33 reviewsStudio vacation home with pool! Walk to the beach!
23–30 Oct
Home in Orleans
4.88 out of 5 average rating, 17 reviews5-bedroom Cape with a pool and yard games.
30 Aug – 6 Sep
Home in Falmouth
5.0 out of 5 average rating, 26 reviewsCheerful residential home with swimming pool
10–17 Jun
Home in Sandwich
4.99 out of 5 average rating, 69 reviews"Cape Escape" luxury home w/pool & beach access.
29 Oct – 5 Nov
Home in North Truro
4.93 out of 5 average rating, 97 reviewsHeated Pool, Beach, Pets, ADA, 5 bath, EV Charge
10–17 Dec
Home in Yarmouth
4.89 out of 5 average rating, 36 reviewsWinslow Acres [heated] Pool Escape; pool May 15
31 Jan – 7 Feb
Home in Eastham
5.0 out of 5 average rating, 9 reviewsModern Beach House w/ Heated Pool & Game Room!
9–16 Oct
Apartment rentals with a pool
Apartment in Dennis
4.83 out of 5 average rating, 18 reviews1BR 2nd Floor Condo with pool
3–10 May
Apartment in Dennis
4.92 out of 5 average rating, 25 reviewsApril promo-Location-5 mins to beach-Pvt balcony
23–30 Aug
Apartment in Brewster
4.97 out of 5 average rating, 39 reviewsOcean Edge 2 Bed 2 Bath, Golf & Resort Free Access
4–11 Nov
Apartment in Dennis
4.83 out of 5 average rating, 65 reviewsComfy Cape Escape! Spacious, Cozy, Close to Beach!
17–24 Dec
Apartment in Brewster
4.87 out of 5 average rating, 23 reviewsStylish Ocean Edge Condo #TheCouplesNest
16–23 Sep
Apartment in Brewster
4.83 out of 5 average rating, 18 reviewsOcean Edge: 2 bed/2 bath - Pool/Gym, Near Beaches
19–26 Jun
Apartment in Brewster
5.0 out of 5 average rating, 52 reviewsOcean Edge Resort/Pool access/2bedroom-2bath Condo
15–22 Jan
Apartment in Truro
4.82 out of 5 average rating, 51 reviewsDesigner Studio Condo with peeks of Cape Cod Bay.
4–11 Sep
Quick stats about holiday 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
$311 SGD before taxes and fees
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