Town of Highlands, New York Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Town of Highlands, New York on RentalSaver.com!

Town of Highlands Rentals

From $308 per night (USD)
VRBO
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Beautiful furnished apartment with antique bedroom set, private entrance and patio, kitchenette, dining area, full bath, ...
From $308 per night (USD)
VRBO
From $348 per night (USD)
VRBO
Updated Home w/ Patio Half Mile to West Point
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This Hudson River haven is perfect for your next visit to Highland Falls! Whether you’re here to visit a loved one at We ...
From $348 per night (USD)
VRBO
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VRBO
Our Rockbound Highland Home - 2 Blocks from Thayer Gate - 1/2 Block to Main St.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This charming historic home is located only 2 blocks from Thayer Gate at the United States Military Academy at West Poin ...
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VRBO
From $347 per night (USD)
Expedia
Stylish 2BR Retreat Steps from Thayer gate FREE private parking/WiFi
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Nestled just above charming Main Street, this freshly updated 2-bedroom apartment is the perfect home base for families ...
From $347 per night (USD)
Expedia
From $736 per night (USD)
VRBO
Bear Mountain House.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to our cozy Garrison cottage steps to Anthony's Nose hiking trail, minutes from the Bear Mountain bridge, 15 min ...
From $736 per night (USD)
VRBO
From $321 per night (USD)
Expedia
West Point at Your Doorstep! Walk to Academy • Mountain Views • Easy Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to your stylish retreat in the heart of Highland Falls! This charming 2-bedroom apartment boasts breathtaking mo ...
From $321 per night (USD)
Expedia
From $1152 per night (USD)
VRBO
Modern Luxurious Country Retreat w/ Sauna + Hot tub 1hr from NYC
Bedrooms:
1
Bathrooms:
5
Sleeps:
10
Escape to a serene modern ranch-style country house and guest cottage nestled on 4 private acres, just 1 hour from NYC. ...
From $1152 per night (USD)
VRBO
From $543 per night (USD)
Expedia
Modern Farmhouse Walking Distance to West Point
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come stay in this newly renovated home with original details and decorated with modern day charm. Walking distance to We ...
From $543 per night (USD)
Expedia
From $431 per night (USD)
VRBO
Cozy House 3 Blocks From West Pt
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to this thoughtfully remodeled Historic 1890s home, just steps away from West Point's Thayer Gate. The house is ...
From $431 per night (USD)
VRBO
From $192 per night (USD)
Expedia
Local Artist Inspired | Walk to WestPoint + King Bed
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This unique place has a style all its own. Local Artist Inspired with a modern feel that's walking distance to West Poin ...
From $192 per night (USD)
Expedia
From $143 per night (USD)
VRBO
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to West Point! Stay at our quiet, cozy, and private apartment in the heart of Highland Falls. Walkable to West P ...
From $143 per night (USD)
VRBO
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Expedia
House on the Babbling Brook - 2m to West Point
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Relax to the the sounds of the flowing brook in this beautiful, restored pre-civil war era home. Veteran owned, 3 mins ...
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Expedia
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VRBO
Cold Spring Private Suite - 2 min from train
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Room in a guest suite Your own room in a home, plus access to shared spaces. Great for remote work Fast wifi at 69 Mbps, ...
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VRBO
From $1107 per night (USD)
VRBO
Historic home at West Point on Main Street. 1 mile from Thayer Gate!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Charming Historic Home with modern amenities near West Point Military Academy. 4 bedrooms upstairs , 1 full bath upstai ...
From $1107 per night (USD)
VRBO
From $274 per night (USD)
VRBO
Charming Cold Spring Village Home
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Discover the charm of the Hudson Valley from your own historic cottage, just five minutes from the train, one hour from ...
From $274 per night (USD)
VRBO
From $577 per night (USD)
Expedia
Modern West Point House near USMA - 3 bed, 2 bath with Hot tub & Fire pit!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
In the picturesque town of Highland Falls, you'll find this cozy three-bedroom retreat perfect for your relaxing holiday ...
From $577 per night (USD)
Expedia
From $309 per night (USD)
VRBO
Lovely 3BR Home with parking-Walk to WP Gate!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Walk to West Point! Enjoy the Hudson Valley. Bring the whole family to this great place with lots of room for fun. Cozy ...
From $309 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Walk to WP Gate + Free Parking!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Enjoy stylish comfort at this centrally located 2 Bedroom apartment. This charming second-floor walkup in a 2-family hou ...
From $336 per night (USD)
Expedia
From $477 per night (USD)
VRBO
Charming Highland Falls Home < 2 Mi to West Point!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Discover the Hudson Valley with this Highland Falls vacation rental as your home base! Situated less than 2 miles from W ...
From $477 per night (USD)
VRBO
From $827 per night (USD)
Expedia
West Point Family Retreat, 5 min walk to Thayer!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
*Graduation 2025, 2026, 2027, 2028 & 2029 and Ring Weekend 2025, 2026, 2027 & 2028 are booked!* Relax in this well ap ...
From $827 per night (USD)
Expedia
From $400 per night (USD)
VRBO
Discover Nature’s Glory! Perfect Family Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Rustling trees, fresh mountain air, and all the time in the world to just slow down and enjoy it. This is everything NY ...
From $400 per night (USD)
VRBO
From $368 per night (USD)
VRBO
Walk to West Point from this 2-bedroom charmer
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Experience the beauty of the Hudson River Valley in this charming, mid-century home. Complete with a full kitchen, dinin ...
From $368 per night (USD)
VRBO
From $531 per night (USD)
VRBO
Room for Everyone: Spacious 6BR West Point Retreat
Bedrooms:
4
Bathrooms:
6
Sleeps:
15
Welcome to our Grand Serene 6-bedroom, 4-bathroom retreat nestled in the heart of Highland Falls, NY, Minutes to West Po ...
From $531 per night (USD)
VRBO
From $485 per night (USD)
Expedia
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Step into serene comfort at our newly constructed 3-bedroom, 2 bathroom (1,228 sqft) Top Floor unit nestled in the neigh ...
From $485 per night (USD)
Expedia
From $228 per night (USD)
VRBO
House on the Babbling Brook- Quiet 2BR + King Bed!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Relax to the the sounds of the flowing brook in this beautiful, restored pre-civil war era home. Tucked away on a dead e ...
From $228 per night (USD)
VRBO
From $245 per night (USD)
Expedia
3BR West Point Retreat-3min to Back Gate+ King Bed
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Relax to the the sounds of the flowing brook in this beautiful, restored pre-civil war era home. Tucked away on a dead e ...
From $245 per night (USD)
Expedia
From $471 per night (USD)
VRBO
5 BR West Point Family Compound- Sleeps 10!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Relax to the the sounds of the flowing brook in this beautiful, restored pre-civil war era home. Tucked away on a dead e ...
From $471 per night (USD)
VRBO
From $920 per night (USD)
VRBO
West Point Mountain House
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to West Point and enjoy early check in & late check out at this beautiful mountainside house overlooking the vil ...
From $920 per night (USD)
VRBO
From $372 per night (USD)
VRBO
2 Bedroom Condo -Views of West Point and Hudson River, steps from Metro North!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to this delightful condo in picturesque Garrison. With 2 queen beds spread across 3 levels, with kitchen, laundry ...
From $372 per night (USD)
VRBO
From $328 per night (USD)
Expedia
Fabulous 3bdrm Home w/parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Your family will be close to everything when you stay at this centrally located home. Easy access to West Point Gate and ...
From $328 per night (USD)
Expedia
From $258 per night (USD)
VRBO
Beautiful First Flr, 2-Bedroom Apt w/ Free Parking
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to this updated and centrally located ground floor apartment that is completely private. Walking distance from W ...
From $258 per night (USD)
VRBO
From $581 per night (USD)
VRBO
Home: 2 Mi to Thayer Gate at U.S. Military Academy
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Multiple Living Areas | Stargazing | 2 Mi to Hudson River | In-Unit Laundry There’s plenty of breathing room for the wh ...
From $581 per night (USD)
VRBO
From $537 per night (USD)
VRBO
Garrison Retreat | Trails & Stream
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to the Garrison Retreat, an exclusive retreat in the heart of the Hudson Valley. Set behind stately stone pillar ...
From $537 per night (USD)
VRBO
From $1285 per night (USD)
VRBO
Garrison Getaway | Pool, Sauna & Gym
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to the Garrison Getaway – Your Ideal Summer Retreat! Just one hour from NYC and five minutes from the charming v ...
From $1285 per night (USD)
VRBO
From $590 per night (USD)
VRBO
Cold Spring Village Maisonette with Pool
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Imagine stepping off the train in the picturesque Village of Cold Spring and strolling up scenic Main Street to your pri ...
From $590 per night (USD)
VRBO
From $194 per night (USD)
Expedia
Cozy 1-bedroom retreat minutes from West Point!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy easy access to everything from this perfectly located home base. Explore the beautiful Hudson Valley, shop the out ...
From $194 per night (USD)
Expedia
From $436 per night (USD)
VRBO
Tranquil 4-bedroom home, 2 miles from West Point, loaded with amenities
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Located in Highland Falls, this comfort house offers 4 bedrooms with a mix of 1 king, 2 full, and 1 twin beds. The 2 bat ...
From $436 per night (USD)
VRBO

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Town of Highlands Rentals

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Results: 37 Rentals