House vacation rentals in Highlands
Find and book unique houses on Airbnb
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
4.96 out of 5 average rating, 223 reviewsMidcentury Modern ZenHouse Sculptor Studio
Home in New Paltz
4.98 out of 5 average rating, 440 reviewsmidcentury modern in ground pool walk 2 trail/town
Home in Putnam Valley
4.93 out of 5 average rating, 182 reviewsPutnam Valley Escape
Home in Pound Ridge
5.0 out of 5 average rating, 126 reviewsPeaceful Light-Filled Guesthouse 1 Hour From NYC
Home in Yorktown Heights
4.88 out of 5 average rating, 120 reviewsCozy winter getaway 1 hr from NYC!
Home in West Milford
4.99 out of 5 average rating, 114 reviewsOn The Rocks In The Hot Tub
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 reviewsSummer Farm Country Escape with Pool and Hot tub.
Weekly house rentals
Home in Greenwood Lake
4.99 out of 5 average rating, 144 reviewsSpectacular Lake Views from Every Room & Garden
Home in Spring Glen
4.98 out of 5 average rating, 102 reviewsCreekside cottage on 65 acres
Home in Carmel Hamlet
4.92 out of 5 average rating, 131 reviewsLux Bungalow on the Lake
Home in Washingtonville
4.91 out of 5 average rating, 162 reviewsRancho Hudsonmonga (NYC-60mi • LEGOLAND-12mi)
Home in Wilton
4.93 out of 5 average rating, 160 reviewsMid Century Modern Cottage
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, 283 reviewsHilltop Hideaway Forest Villa on 13 acres!
Private house rentals
Home in Highland Falls
4.96 out of 5 average rating, 57 reviewsGrad owned cozy 5 bd home right outside West Point
Home in Highland Falls
4.97 out of 5 average rating, 73 reviewsBear Mountain, Westpoint, & Hikers Retreat
Home in Highland Falls
5.0 out of 5 average rating, 15 reviewsGRAD MOM House 3 Queen 2 Bath
Home in Highland Falls
5.0 out of 5 average rating, 34 reviewsLuxe West Point Retreat: 3BR/2BA w/HotTub, FirePit
Home in Highland Falls
5.0 out of 5 average rating, 73 reviewsCozy House 3 Blocks From West Pt
Home in Putnam Valley
4.96 out of 5 average rating, 71 reviewsModern Mountain Retreat w/ panoramic views
Home in Washingtonville
5.0 out of 5 average rating, 10 reviewsThe Hideaway on 5 Acres with Heated Pool
Home in Newburgh
5.0 out of 5 average rating, 89 reviewsHillcrest Glasshouse - a minimalist modern retreat
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
Destinations to explore
- New City Vacation rentals
- Long Island Vacation rentals
- Newark Vacation rentals
- Pocono Mountains Vacation rentals
- Hoboken Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Tiny house rentals New York
- Townhouse rentals New York
- Guesthouse rentals New York
- Lakehouse rentals New York
- House rentals New York
- Beach house rentals New York
- Earth house rentals United States
- House rentals United States
- Guesthouse rentals United States
- Lighthouse rentals United States
- Townhouse rentals United States
- House rentals Manhattan
- Townhouse rentals Manhattan
- Guesthouse rentals Manhattan
- Guesthouse rentals Brooklyn
- House rentals Brooklyn
- Townhouse rentals Brooklyn
- Tiny house rentals New York
- Townhouse rentals New York
- Treehouse rentals New York
- House rentals New York
- Guesthouse rentals New York
- House rentals Orange County
- Guesthouse rentals Orange County
- Rentals with breakfast Highlands
- Monthly Rentals Highlands
- Rentals with outdoor seating Highlands
- Kid-friendly rentals Highlands
- Rentals with pools Highlands
- Pet-friendly rentals Highlands
- Rentals with a fireplace Highlands
- Rentals with a patio Highlands
- Family-friendly rentals Highlands
- Apartment rentals Highlands
- Waterfront rentals Highlands
- Rentals with a fire pit Highlands
- Rentals with a washer and dryer Highlands
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes