House vacation rentals in Highlands
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Top-rated house rentals in Highlands
Guests agree: these houses 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 house rentals
House rentals with a pool
Home in Stamford
4.97 out of 5 average rating, 220 reviewsMidcentury Modern ZenHouse Sculptor Studio
Dec 25 – Jan 1
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Dec 28 – Jan 4
Home in New Paltz
4.98 out of 5 average rating, 437 reviewsmidcentury modern in ground pool walk 2 trail/town
Jun 3 – 10
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 Woodstock
4.98 out of 5 average rating, 101 reviewsWoodstock Historic Artist Estate- The Museum House
Mar 7 – 14
Home in Yorktown Heights
4.88 out of 5 average rating, 119 reviewsCozy winter getaway 1 hr from NYC!
Jun 16 – 23
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
Jul 25 – Aug 1
Weekly house rentals
Home in Carmel Hamlet
4.92 out of 5 average rating, 130 reviewsLux Bungalow on the Lake
Aug 23 – 30
Home in Wilton
4.93 out of 5 average rating, 160 reviewsMid Century Modern Cottage
Oct 8 – 15
Home in Cornwall-on-Hudson
4.92 out of 5 average rating, 131 reviewsCozy Riverfront Victorian in the Hudson Valley
Jan 14 – 21
Home in Tomkins Cove
4.94 out of 5 average rating, 137 reviewsHudson Valley Victorian with River Views
Aug 5 – 12
Home in Kerhonkson
4.97 out of 5 average rating, 108 reviewsFarmhouse Fantasy!
Jun 26 – Jul 3
Home in Greenwood Lake
4.99 out of 5 average rating, 142 reviewsSpectacular Lake Views from Every Room & Garden
Oct 19 – 26
Home in Danbury
4.99 out of 5 average rating, 336 reviewsBEAUTIFUL PRIVATE APARTMENT SUITE IN DANBURY CT!!
Apr 21 – 28
Home in Kingston
4.97 out of 5 average rating, 278 reviewsThis New House
Dec 15 – 22
Private house rentals
Home in Highland Falls
5.0 out of 5 average rating, 29 reviewsLuxe West Point Retreat: 3BR/2BA w/HotTub, FirePit
Aug 3 – 10
Home in Highland Falls
5.0 out of 5 average rating, 15 reviewsGRAD MOM House 3 Queen 2 Bath
Dec 2 – 9
Home in Highland Falls
5.0 out of 5 average rating, 18 reviewsHighland Falls Home - 1/2 Mile to West Point
Jan 3 – 10
Home in Highland Falls
4.96 out of 5 average rating, 52 reviewsWest Point Mountain House
Sep 2 – 9
Home in Highland Falls
4.96 out of 5 average rating, 91 reviewsEnjoy Walking Privileges! WestPoint Farmhouse
Jan 18 – 25
Home in Highland Falls
5.0 out of 5 average rating, 70 reviewsCozy House 3 Blocks From West Pt
Apr 26 – May 3
Home in Putnam Valley
5.0 out of 5 average rating, 38 reviewsLuxury Lake House Sauna 1h From NYC
Dec 25 – Jan 1
Home in Putnam Valley
4.96 out of 5 average rating, 71 reviewsModern Mountain Retreat w/ panoramic views
Dec 6 – 13
Quick stats about house rentals in Highlands
Total rentals
110 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
90 properties are a good fit for families
Total number of reviews
3.4K reviews
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