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
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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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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 $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 $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 $336 per night (USD)VRBO
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)VRBO
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)VRBO
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)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 $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 $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 $258 per night (USD)Expedia
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)Expedia
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