Cottages in Town of Highlands

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Town of Highlands

Luxe Family Home on Orange Lake w/ Private Dock!
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Luxe Family Home on Orange Lake w/ Private Dock!

3.0 star property
Luxe Family Home on Orange Lake w/ Private Dock!
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Interior

Hudson Valley Retreat w/ Pool Near Greenwood Lake

3.0 star property
10.0 out of 10, Exceptional, (1)
"Excelent House 👏👌👌"
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Family Home Close to Warwick, 5 Mi to Lake!
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Family Home Close to Warwick, 5 Mi to Lake!

3.0 star property
Family Home Close to Warwick, 5 Mi to Lake!
Bright Cornwall-on-hudson Vacation Rental!
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Bright Cornwall-on-hudson Vacation Rental!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice property, very comfortable, close to multiple sightseeing location including bear mountain."
Bright Cornwall-on-hudson Vacation Rental!
Hudson River Views + Firepit, Patio, Dog Run, Game Room Stone Manor
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Hudson River Views + Firepit, Patio, Dog Run, Game Room Stone Manor

3.0 star property
Hudson River Views + Firepit, Patio, Dog Run, Game Room Stone Manor
Pet-friendly Hopewell Junction Home w/ Pool
Outdoor dining

Pet-friendly Hopewell Junction Home w/ Pool

3.0 star property
10.0 out of 10, Exceptional, (1)
"This house was so incredible. Not only was it in a quiet nice neighborhood the inside was incredible too. Pool table as well as a pool it was perfect for my stay to have fun and enjoy our time. They were very communicative and welcoming to their house. Everything was comfortable and clean. Can’t say any bad things about this place. Definitely going to book again. I already miss it. "
Pet-friendly Hopewell Junction Home w/ Pool
Charming Victorian Retreat w/ Hudson River Views
Interior

Charming Victorian Retreat w/ Hudson River Views

3.0 star property
Charming Victorian Retreat w/ Hudson River Views
Charming Highland Falls Home < 2 Mi to West Point!
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Charming Highland Falls Home < 2 Mi to West Point!

3.0 star property
Charming Highland Falls Home < 2 Mi to West Point!
Serene Holmes Cottage Near Lakes & Trails!
Front of property

Serene Holmes Cottage Near Lakes & Trails!

3.0 star property
Serene Holmes Cottage Near Lakes & Trails!
Historic 1800s Cornwall-on-hudson Cottage!
Interior

Historic 1800s Cornwall-on-hudson Cottage!

3.0 star property
Historic 1800s Cornwall-on-hudson Cottage!
Waterfront Wallkill Duplex Home w/ Fire Pits!
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Waterfront Wallkill Duplex Home w/ Fire Pits!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great for my kids and family for options to play outdoors and indoors games together. Loved the coffee bar and the details in the bathrooms with all the little things we could use down to the qtips and things. Really great for our family trip memories!!"
Waterfront Wallkill Duplex Home w/ Fire Pits!
Fire Pit + On-site Pond: Hudson Valley Home!
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Fire Pit + On-site Pond: Hudson Valley Home!

3.0 star property
Fire Pit + On-site Pond: Hudson Valley Home!
Updated Home w/ Patio Half Mile to West Point
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Updated Home w/ Patio Half Mile to West Point

3.0 star property
Updated Home w/ Patio Half Mile to West Point
Dreamy Hudson Valley Cottage w/ State Park Views
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Dreamy Hudson Valley Cottage w/ State Park Views

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was amazing with great amenities. The kitchen was stocked with all the utensils and cutlery. The patio was a good addition. Overall great stay! "
Dreamy Hudson Valley Cottage w/ State Park Views
Warwick Vacation Rental w/ Private Yard & Fire Pit
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Warwick Vacation Rental w/ Private Yard & Fire Pit

3.0 star property
10.0 out of 10, Exceptional, (1)
"I was relieved to find that the property looks just like and even better than the pictures online. "
Warwick Vacation Rental w/ Private Yard & Fire Pit
Relaxing New York Home w/ Boat Dock & Lake View!
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Relaxing New York Home w/ Boat Dock & Lake View!

3.0 star property
Relaxing New York Home w/ Boat Dock & Lake View!
Cozy Campbell Hall Getaway w/ Porch!
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Cozy Campbell Hall Getaway w/ Porch!

3.0 star property
Cozy Campbell Hall Getaway w/ Porch!
Lakefront Brewster Vacation Rental w/ Private Dock
Interior

Lakefront Brewster Vacation Rental w/ Private Dock

3.0 star property
Lakefront Brewster Vacation Rental w/ Private Dock
Luxe Montgomery Home w/ Hot Tub Near Angry Orchard
Exterior

Luxe Montgomery Home w/ Hot Tub Near Angry Orchard

3.0 star property
Luxe Montgomery Home w/ Hot Tub Near Angry Orchard
Outdoor Entertainment Areas: Spacious Katonah Gem!
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Outdoor Entertainment Areas: Spacious Katonah Gem!

3.0 star property
Outdoor Entertainment Areas: Spacious Katonah Gem!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Town of Highlands Hotel Reviews

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"Great experience from the moment we walked in. Very helpful staff (needed a roll away bed for my family, and they accommodated very nicely). The room was spacious and nice, very clean and comfortable. Breakfast was a also great, along with the pool. Would recommend and stay here again "
William 1-night trip
Posted 1 day ago
Hampton Inn Harriman Woodbury