- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Top cities in Town of Highlands

West Point

Bear Mountain

Highland Falls

Fort Montgomery
Find vacation rentals that suit your style

Apartments

Aparthotels

Villas

Cottages

Cabins

Condos

Chalets
Our top choices for Town of Highlands villas




1. The Scenic Mansion With Breathtaking View
The Scenic Mansion With Breathtaking ViewHighland
8.0 out of 10, Very good, (24 reviews)
8.0/10
Very good
(24 reviews)
"The house was very clean and even more impressive in person. The rooms were large and there was plenty of room for all us. We had a minor plumbing issue which was quickly resolved by the responsive host. Our whole group loved gathering around the firepit every night and enjoying the magnificent view. The pool is huge, but needs some maintenance (diving board cracking) and the chemicals balanced. The kitchen needs more silverware. Overall, we had a great stay."
"The house was very clean and even more impressive in person. The rooms were large and there was plenty of room for all us. We had a minor plumbing issue which was quickly resolved by the responsive host. Our whole group loved gathering around the firepit every night and enjoying the magnificent view. The pool is huge, but needs some maintenance (diving board cracking) and the chemicals balanced. The kitchen needs more silverware. Overall, we had a great stay."Mary R.




2. Serene 10BR Retreat w/Pool, Gym, Hot Tub & Sauna
Serene 10BR Retreat w/Pool, Gym, Hot Tub & SaunaChester
8.0 out of 10, Very good, (3 reviews)
8.0/10
Very good
(3 reviews)
"This is a fantastic place to gather the whole family together. The kitchen was capable of feeding our large group, with plenty of utensils, plates, cups, pots and pans.So many sleeping options to fit everyone's needs and enough hot water to go around:) I never once waited in line to use the restroom.The pool, though covered during our stay, was definitely calling us to return for another group getaway in the future"
"This is a fantastic place to gather the whole family together. The kitchen was capable of feeding our large group, with plenty of utensils, plates, cups, pots and pans.So many sleeping options to fit everyone's needs and enough hot water to go around:) I never once waited in line to use the restroom.The pool, though covered during our stay, was definitely calling us to return for another group getaway in the future"Heather W.




3. 7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living SpaceMonroe
6.8 out of 10, (8 reviews)
6.8/10
(8 reviews)
"It was a great home with lots of space indoor and outside. "
"It was a great home with lots of space indoor and outside. "Yogita R.




4. Magical Family Escape, Pool, HotTub, Pets, <1 Hr NYC
Magical Family Escape, Pool, HotTub, Pets, <1 Hr NYCHarriman
10.0 out of 10, Exceptional, (83 reviews)
10/10
Exceptional
(83 reviews)
"We used the hot tub and loved it. It was very easy to have our dog with us"
"We used the hot tub and loved it. It was very easy to have our dog with us"Julie M.




5. Spectacular Historic Mansion w/Pool&Tennis
Spectacular Historic Mansion w/Pool&TennisGoshen
10.0 out of 10, Exceptional, (20 reviews)
10/10
Exceptional
(20 reviews)
"Truly amazing house, incredible pool, easy renting experience. Would definitely be back. "
"Truly amazing house, incredible pool, easy renting experience. Would definitely be back. "Aditya U.
The price is AED 5,869
AED 5,869
AED 8,960 total
includes taxes & fees
15 Nov - 16 Nov




6. 11BR Retreat w Pool & Game Room
11BR Retreat w Pool & Game RoomChester
10.0 out of 10, Exceptional, (2 reviews)
10/10
Exceptional
(2 reviews)
"5 star experience! We will definitely stay here again. The host was responsive, and the house was in perfect condition. The pool was clean. The sauna was spotless!"
"5 star experience! We will definitely stay here again. The host was responsive, and the house was in perfect condition. The pool was clean. The sauna was spotless!"Benny P.




7. Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
Magnificent Villa, Private Pool, Fire Pit w/Huge BackyardChester
9.6 out of 10, Exceptional, (17 reviews)
9.6/10
Exceptional
(17 reviews)
"Our family was pleased with every thing this property offered"
"Our family was pleased with every thing this property offered"Carla A.




8. Spacious Retreat w/ Pool, Hot Tub & Game Room
Spacious Retreat w/ Pool, Hot Tub & Game RoomStony Point
4.0 out of 10, (1 review)
4.0/10
(1 review)
"The house itself was fine but the pool was unusable and not maintained. We were frequently promised it would be fixed each day but there was no maintenance done. Even going through support, there was no attempt to make things right and we were unable to use the pool during a hot summer weekend. (There aren't even any pool towels for use)"
"The house itself was fine but the pool was unusable and not maintained. We were frequently promised it would be fixed each day but there was no maintenance done. Even going through support, there was no attempt to make things right and we were unable to use the pool during a hot summer weekend. (There aren't even any pool towels for use)"Kevin L.




9. Group Retreat w. Backyard, BBQ, Gym, Games & More!
Group Retreat w. Backyard, BBQ, Gym, Games & More!Stony Point
9.6 out of 10, Exceptional, (5 reviews)
9.6/10
Exceptional
(5 reviews)
"Great place with ample room for our large party of 15 to celebrate the holidays! Hosts were very communicative and helpful. Only opportunity for improvement would be to increase kitchen stock items (plates glasses bowls utensils etc) and add another bathroom. Thanks for a great stay! "
"Great place with ample room for our large party of 15 to celebrate the holidays! Hosts were very communicative and helpful. Only opportunity for improvement would be to increase kitchen stock items (plates glasses bowls utensils etc) and add another bathroom. Thanks for a great stay! "Family T.




10. Spacious villa w/Pool, Hot Tub, Sauna & Game Room on 7.5 private acres
Spacious villa w/Pool, Hot Tub, Sauna & Game Room on 7.5 private acresChester
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.
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.
Top reviews in Town of Highlands




The Thayer Hotel at West Point
The Thayer Hotel at West PointWest Point
10/10 Excellent
I like the castle and 1800s feel with the luxury of today. I would like to know more of the history of the building.
I like the castle and 1800s feel with the luxury of today. I would like to know more of the history of the building.
Amy




Overlook Lodge at Bear Mountain
Overlook Lodge at Bear MountainBear Mountain
10/10 Excellent
Just did a quick overnight stay but was friendly and clean
Just did a quick overnight stay but was friendly and clean
Giuseppe




The Abbey Inn & Spa
The Abbey Inn & SpaPeekskill
10/10 Excellent
Very nice hotel although immediate hotel surroundings not that attractive.
Very nice hotel although immediate hotel surroundings not that attractive.
Ralph




SpringHill Suites by Marriott Fishkill
SpringHill Suites by Marriott FishkillFishkill
10/10 Excellent
The hotel was clean and the free breakfast was delicious. The staffs were also approachable and friendly. Would highly recommend.
The hotel was clean and the free breakfast was delicious. The staffs were also approachable and friendly. Would highly recommend.
MICHELLE




The Orange Inn Boutique Hotel
The Orange Inn Boutique HotelGoshen
10/10 Excellent
Well maintained and clean property , inside and out. We could have gotten more of an overview of the property when we checked in, but we managed. Ample parking available in their parking lot in the back. One thing I was surprised about -for a luxury inn , they had polyester sheets instead of cotton sheets. Overall great stay.
Well maintained and clean property , inside and out. We could have gotten more of an overview of the property when we checked in, but we managed. Ample parking available in their parking lot in the back. One thing I was surprised about -for a luxury inn , they had polyester sheets instead of cotton sheets. Overall great stay.
Kevin




The Dominion House Bed & Breakfast
The Dominion House Bed & BreakfastChester
10/10 Excellent
Lovely period home. Owners were friendly, courteous and informative. Breakfast was delicious. Overall stay was very enjoyable and would stay again.
Lovely period home. Owners were friendly, courteous and informative. Breakfast was delicious. Overall stay was very enjoyable and would stay again.
Cindy




Mirbeau Inn & Spa Beacon
Mirbeau Inn & Spa BeaconBeacon
10/10 Excellent
Gorgeous property
Gorgeous property
EDUARD




Sleep Inn & Suites Monroe - Woodbury
Sleep Inn & Suites Monroe - WoodburyMonroe
10/10 Excellent
Everything was great! From the actual rooms to the delicious breakfast served every morning.
Everything was great! From the actual rooms to the delicious breakfast served every morning.
Lisyani




Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHG
Holiday Inn Express & Suites Peekskill-Lower Hudson Valley by IHGPeekskill
10/10 Excellent
Very nice lodging across the street from a riverside park and walking trail.
Very nice lodging across the street from a riverside park and walking trail.
David Allen




Residence Inn by Marriott Fishkill
Residence Inn by Marriott FishkillFishkill
10/10 Excellent
Great stay
Great stay
Renaud




The Dutchess Inn and Spa at Beacon
The Dutchess Inn and Spa at BeaconBeacon
10/10 Excellent
The cleanliness, courteous and friendly staffers.
The cleanliness, courteous and friendly staffers.
Marjorie




Homewood Suites Stewart Airport
Homewood Suites Stewart AirportNew Windsor
10/10 Excellent
Needed a place to stay when moving to the area. This hotel was conveniently located and very affordable - especially considering what you get! The suites were fantastic - spacious, everything we needed, kitchenettes. On top of that they serve a good hot breakfast every morning and a manager's reception (which is essentially a meal) four nights a week. What a deal! Friendly, helpful staff too. I truly don't have anything negative to say about this hotel.
Needed a place to stay when moving to the area. This hotel was conveniently located and very affordable - especially considering what you get! The suites were fantastic - spacious, everything we needed, kitchenettes. On top of that they serve a good hot breakfast every morning and a manager's reception (which is essentially a meal) four nights a week. What a deal! Friendly, helpful staff too. I truly don't have anything negative to say about this hotel.
Anonymous traveler
