Holiday rentals with a pool in Highlands
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Highlands
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 Highlands rentals with a pool
House rentals with a pool
Home in Pound Ridge
5.0 out of 5 average rating, 126 reviewsPeaceful Light-Filled Guesthouse 1 Hour From NYC
Home in Woodstock
4.98 out of 5 average rating, 101 reviewsWoodstock Historic Artist Estate- The Museum House
Home in West Milford
4.99 out of 5 average rating, 113 reviewsOn The Rocks In The Hot Tub
Home in Middletown
4.94 out of 5 average rating, 100 reviewsSpringtime farm escape with hot tub and amenities
Home in Cottekill
4.95 out of 5 average rating, 243 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Home in Woodstock
4.91 out of 5 average rating, 212 reviewsJapanese Teahouse & Onsen, outside shower, tennis
Home in Highland Falls
4.96 out of 5 average rating, 50 reviewsWest Point Hudson Valley Getaway
Apartment rentals with a pool
Apartment in Vernon Township
4.76 out of 5 average rating, 137 reviews1 Bedroom Condo @ Appalachian Resort Hotel
Apartment in Vernon Township
4.97 out of 5 average rating, 217 reviewsRustic Chic at Mountain Creek! Pool Open All Year!
Apartment in Vernon Township
4.9 out of 5 average rating, 129 reviewsLodge style getaway 50 miles from NYC patio 207
Apartment in Vernon Township
4.94 out of 5 average rating, 104 reviewsResort Getaway-Mtn Creek Ski/Pool/Hot Tub/Sauna
Apartment in Vernon Township
4.9 out of 5 average rating, 203 reviewsUpscale Condo Ski-In/Out Mountain Creek 1 hr NYC
Apartment in Vernon
4.94 out of 5 average rating, 125 reviewsMtn front Resort Pool Hot Tub Sauna Best View 340
Apartment in Vernon Township
4.93 out of 5 average rating, 95 reviewsValley Overlook @ Mtn Creek Resort Park & Play
Apartment in Vernon Township
5.0 out of 5 average rating, 27 reviewsLittle Getaway at the Black Creek Sanctuary
Home rentals with a private pool
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
Home in Lagrangeville
4.84 out of 5 average rating, 121 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
Home in Rhinebeck
5.0 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
Quick stats about holiday rentals with a pool in Highlands
Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
990 reviews
Nightly prices starting at
£48 before taxes and fees
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