
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

Heated Pool, Game Room, Projector Room, Private

5-bedroom Cape with a pool and yard games.

Exclusive New Seabury Home w/ Heated Pool ⛳️🏖🦞☀️🐠

4 BD slice of Harwich Heaven

Home in Hyannis Port

Private Pool, near beaches, 3 BR/3 BA, Central Air

New listing 4bd w/ heated pool and chicken coop

Room for multiple families!
Condo rentals with a pool

P-Town Beach Beauty on the Bay. Water View!

1BR 2nd Floor Condo with pool

Comfy Cape Escape! Spacious, Cozy, Close to Beach!

Ocean Edge: 2 bed/2 bath - Pools & Resort Access

Sunny 2bedroom condo w pool, walk to town

Spectacular Waterfront Condo

Modern, clean waterviews

Golf Course Views and Pools
Quick stats about vacation rentals with a pool in Chatham
Total rentals
40 properties
Nightly prices starting at
ﺩ.ﺇ588 before taxes and fees
Total number of reviews
320 reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi
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- Cape Cod
- Mayflower Beach
- West Dennis Beach
- East Sandwich Beach
- Craigville Beach
- Duxbury Beach
- Coast Guard Beach
- Sandwich Glass Museum
- Owen Park Beach
- Nickerson State Park
- Onset Beach
- Oyster Harbors Beach
- Inman Road Beach
- White Horse Beach
- Pinehills Golf Club
- Kalmus Park Beach
- Ridgevale Beach
- Chapin Memorial Beach
- Forest Beach
- Linnell Landing Beach
- Corporation Beach
- Cape Cod National Seashore
- Lighthouse Beach
- Ellis Landing Beach