House holiday 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.
Holiday 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 Putnam Valley
4.93 out of 5 average rating, 182 reviewsPutnam Valley Escape
Home in New Paltz
4.98 out of 5 average rating, 438 reviewsmidcentury modern in ground pool walk 2 trail/town
Home in Pound Ridge
5.0 out of 5 average rating, 126 reviewsPeaceful Light-Filled Guesthouse 1 Hour From NYC
Home in West Milford
4.99 out of 5 average rating, 114 reviewsOn The Rocks In The Hot Tub
Home in Stamford
4.97 out of 5 average rating, 221 reviewsMidcentury Modern ZenHouse Sculptor Studio
Home in Yorktown Heights
4.88 out of 5 average rating, 120 reviewsCozy winter getaway 1 hr from NYC!
Home in Woodstock
4.98 out of 5 average rating, 101 reviewsWoodstock Historic Artist Estate- The Museum House
Home in Middletown
4.94 out of 5 average rating, 101 reviewsSpringtime farm escape with hot tub and amenities
Weekly house rentals
Home in Tomkins Cove
4.94 out of 5 average rating, 138 reviewsHudson Valley Victorian with River Views
Home in Putnam Valley
4.89 out of 5 average rating, 254 reviewsThe Pudding Pad Lake House
Home in Cold Spring
4.95 out of 5 average rating, 282 reviewsHilltop Hideaway Forest Villa on 13 acres!
Home in Kingston
4.96 out of 5 average rating, 280 reviewsThis New House
Home in Mahopac
4.98 out of 5 average rating, 130 reviewsPeaceful & Spacious Retreat
Home in Carmel Hamlet
4.92 out of 5 average rating, 131 reviewsLux Bungalow on the Lake
Home in Highland Falls
4.84 out of 5 average rating, 61 reviewsLovely 3BR Home with parking-Walk to WP Gate!
Home in Highland Falls
4.97 out of 5 average rating, 72 reviewsBear Mountain, Westpoint, & Hikers Retreat
Private house rentals
Home in Highland Falls
5.0 out of 5 average rating, 18 reviewsHighland Falls Home - 1/2 Mile to West Point
Home in Mohegan Lake
4.97 out of 5 average rating, 32 reviewsA nice place to getaway
Home in Highland Falls
4.96 out of 5 average rating, 50 reviewsWest Point Hudson Valley Getaway
Home in Highland Falls
4.96 out of 5 average rating, 91 reviewsEnjoy Walking Privileges! WestPoint Farmhouse
Home in Highland Falls
5.0 out of 5 average rating, 33 reviewsLuxe West Point Retreat: 3BR/2BA w/HotTub, FirePit
Home in Highland Falls
5.0 out of 5 average rating, 72 reviewsCozy House 3 Blocks From West Pt
Home in Cornwall
4.98 out of 5 average rating, 65 reviewsMountain Retreat, Cornwall, NY
Home in Fort Montgomery
5.0 out of 5 average rating, 31 reviewsSpectacular River& Mountain views near West Point!
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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