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 Woodstock
4.98 out of 5 average rating, 101 reviewsWoodstock Historic Artist Estate- The Museum House
Nov 25 – Dec 2
Home in Middletown
4.94 out of 5 average rating, 100 reviewsSpringtime farm escape with hot tub and amenities
Dec 22 – 29
Home in Downsville
4.97 out of 5 average rating, 110 reviewsTrout fishing on the Delaware
Jan 10 – 17
Home in Cottekill
4.95 out of 5 average rating, 242 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Dec 20 – 27
Home in Narrowsburg
4.97 out of 5 average rating, 141 reviewsModern Ranch With Pool & Hot-Tub
Sep 29 – Oct 6
Home in Cornwall-on-Hudson
4.86 out of 5 average rating, 88 reviewsEclectic, Sleeps 5, Wsher/Dryer, Parking, Yard, AC
Apr 9 – 16
Home in Philipstown
5.0 out of 5 average rating, 13 reviewsModern Cottage in the Woods, Garrison
May 12 – 19
Home in Highland Falls
4.96 out of 5 average rating, 50 reviewsWest Point Hudson Valley Getaway
Nov 29 – Dec 6
Condo rentals with a pool
Condo in Vernon Township
4.97 out of 5 average rating, 222 reviewsAppalachian Mt. View 1 Bdrm Suite 3rd Flr Balcony
Dec 13 – 20
Condo in Vernon Township
4.95 out of 5 average rating, 733 reviewsAppalachian Lodge Top Floor w/views
Sep 16 – 23
Condo in Vernon Township
4.97 out of 5 average rating, 217 reviewsRustic Chic at Mountain Creek! Pool|Hot Tub|Sauna
Nov 21 – 28
Condo in Vernon Township
4.76 out of 5 average rating, 137 reviews1 Bedroom Condo @ Appalachian Resort Hotel
Sep 28 – Oct 5
Condo in Vernon Township
4.95 out of 5 average rating, 240 reviewsNYC Escape 1 hr away
Oct 8 – 13
Condo in Vernon Township
4.94 out of 5 average rating, 104 reviewsResort Getaway-Mtn Creek Ski/Pool/Hot Tub/Sauna
Nov 29 – Dec 6
Condo in Vernon Township
4.9 out of 5 average rating, 203 reviewsUpscale Condo Ski-In/Out Mountain Creek 1 hr NYC
Nov 15 – 22
Condo in Vernon
4.94 out of 5 average rating, 125 reviewsMtn front Resort Pool Hot Tub Sauna Best View 340
Jul 19 – 26
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 9 – 16
Home in Lagrangeville
4.84 out of 5 average rating, 120 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
Oct 22 – 29
Farm stay in Fleischmanns
4.91 out of 5 average rating, 11 reviewsEscape to a Dreamy 1857 Farmhouse in Fleischmanns
Nov 3 – 10
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
Sep 3 – 10
Home in Lanesville
4.77 out of 5 average rating, 205 reviewsGo Hiking and Skiing from a Family-Friendly Farmhouse
Oct 8 – 15
Home in Rhinebeck
5.0 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
Oct 4 – 11
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
€ 56 before taxes and fees
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