Vacation 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.
Vacation 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
Dec 14 – 21
Home in Yorktown Heights
4.88 out of 5 average rating, 119 reviewsCozy winter getaway 1 hr from NYC!
Sep 15 – 22
Home in Woodstock
4.98 out of 5 average rating, 101 reviewsWoodstock Historic Artist Estate- The Museum House
Sep 6 – 13
Home in West Milford
4.99 out of 5 average rating, 113 reviewsOn The Rocks In The Hot Tub
Oct 3 – 10
Home in Middletown
4.94 out of 5 average rating, 100 reviewsSpringtime farm escape with hot tub and amenities
Jan 5 – 12
Home in Downsville
4.97 out of 5 average rating, 110 reviewsTrout fishing on the Delaware
Jan 8 – 15
Home in Cottekill
4.95 out of 5 average rating, 242 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Aug 23 – 30
Home in Narrowsburg
4.97 out of 5 average rating, 141 reviewsModern Ranch With Pool & Hot-Tub
Sep 27 – Oct 4
Condo rentals with a pool
Condo in Vernon Township
4.95 out of 5 average rating, 239 reviewsNYC Escape 1 hr away
Aug 13 – 18
Condo in Vernon Township
4.97 out of 5 average rating, 222 reviewsAppalachian Mt. View 1 Bdrm Suite 3rd Flr Balcony
Mar 8 – 15
Condo in Vernon Township
4.76 out of 5 average rating, 137 reviews1 Bedroom Condo @ Appalachian Resort Hotel
Sep 26 – Oct 3
Condo in Vernon Township
4.94 out of 5 average rating, 104 reviewsResort Getaway-Mtn Creek Ski/Pool/Hot Tub/Sauna
Nov 27 – Dec 4
Condo in Vernon Township
4.9 out of 5 average rating, 203 reviewsUpscale Condo Ski-In/Out Mountain Creek 1 hr NYC
Aug 28 – Sep 4
Condo in Vernon
4.94 out of 5 average rating, 125 reviewsMtn front Resort Pool Hot Tub Sauna Best View 340
Jul 2 – 9
Condo in Tannersville
5.0 out of 5 average rating, 34 reviewsModern 3BR Townhouse Minutes from Ski & Trails
Aug 7 – 14
Condo in Vernon Township
4.93 out of 5 average rating, 94 reviewsValley Overlook @ Mtn Creek Resort Park & Play
Sep 15 – 22
Home rentals with a private pool
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
Sep 10 – 17
Home in Lagrangeville
4.84 out of 5 average rating, 120 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
Sep 27 – Oct 4
Farm stay in Fleischmanns
4.91 out of 5 average rating, 11 reviewsEscape to a Dreamy 1857 Farmhouse in Fleischmanns
Jan 23 – 30
Home in Lanesville
4.77 out of 5 average rating, 205 reviewsGo Hiking and Skiing from a Family-Friendly Farmhouse
Mar 14 – 21
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
Sep 1 – 8
Home in Rhinebeck
5.0 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
Oct 2 – 9
Quick stats about vacation 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
G$12,530 GYD before taxes and fees
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