
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

Stunningly Designed Luxury Home w/ Pool & Hot Tub

4Br Mountain Brook House on 130 acres w/ trails

Stunning luxury home with pool

BoHo Scandi Farm Retreat, Fireplace, Dogs Welcome

Modern & Cozy Lake Oasis ~ Hot Tub ~ Games ~ View

Farmhouse and Guesthouse w Pool, Pond and Sauna!

Sunbeam Lodge: Pool+Hot Tub, 50 Acres, ‘70s Oasis

Hudson River estate guest cottage
Condo rentals with a pool

Cozy Gem with Mountain Views

Luxury. 5-Star. Ski In/Out, Heated Pool, Hot Tub

Windham Condo

Hideaway Windham/Hunter Fireplace Autumn & Foliage

Autumn Retreat w/wood burning fireplace

Jiminy Peak Apartment

Wyndham Bentley Brook

Jiminy Peak Country Inn - ski in/out condo MT view
Other vacation rentals with a pool

Stunning horse farm apt, hot tub

Modern Glass House

Poolside Woodlawn Getaway

Private Cabin in the Woods w/ Hot Tub near Hudson

Catskills Lake Community Escape near Hudson

16 Acre Hudson Hideaway and Pool

Modern 4 season lakefront rental

The Cabbage ~ A place to create/relax/restore.
Destinations to explore
- Plainview Vacation rentals
- New York City Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Philadelphia Vacation rentals
- Mount Pocono Vacation rentals
- Jersey Shore Vacation rentals
- Ocean City Vacation rentals
- Hunter Mountain
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Belleayre Mountain Ski Center
- Berkshire East Mountain Resort
- John Boyd Thacher State Park
- Howe Caverns
- Bash Bish Falls State Park
- Kent Falls State Park
- Zoom Flume
- Walkway Over the Hudson State Historic Park
- Catamount Mountain Ski Resort
- Mount Greylock Ski Club
- Windham Mountain
- Saratoga Spa State Park
- Norman Rockwell Museum
- Taconic State Park
- Opus 40
- Mohawk Mountain Ski Area
- Mount Tom State Reservation
- Beartown State Forest
- Hunter Mountain Resort
- Bousquet Mountain Ski Area
- Albany Center Gallery