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Highland Falls Holiday Rentals

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50 rentals in Highland Falls.
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West Point - Bear Mountain - Woodbury Commons, holiday rental in Highland Falls

West Point - Bear Mountain - Woodbury Commons

3 bedrooms
1 bathroom
Sleeps 7
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NEW! Updated Home w/ Patio Half Mile to West Point, holiday rental in Highland Falls

NEW! Updated Home w/ Patio Half Mile to West Point

3 bedrooms
2 bathrooms
Sleeps 6
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Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View, holiday rental in Highland Falls

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

2 bedrooms
2 bathrooms
Sleeps 6
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Orchard Hill + SANITIZED -1hr NYC, Remote, Corporate Retreats, Spacious, Private, holiday rental in Highland Falls

Orchard Hill + SANITIZED -1hr NYC, Remote, Corporate Retreats, Spacious, Private

8 bedrooms
5 bathrooms
Sleeps 25
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Modern Lake house - Private dock  - 35 miles Out of NYC, holiday rental in Highland Falls

Modern Lake house - Private dock - 35 miles Out of NYC

3 bedrooms
3 bathrooms
Sleeps 12
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Cozy Cottage minutes to West Point, holiday rental in Highland Falls

Cozy Cottage minutes to West Point

3 bedrooms
3 bathrooms
Sleeps 8
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Cosy lakefront cottage in Hudson Valley, holiday rental in Highland Falls

Cosy lakefront cottage in Hudson Valley

1 bedroom
1 bathroom
Sleeps 2
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Beautiful 1850's brick farm house in Beacon - 4 bdrm, 2 1/2 bath, entire house., holiday rental in Highland Falls

Beautiful 1850's brick farm house in Beacon - 4 bdrm, 2 1/2 bath, entire house.

4 bedrooms
3 bathrooms
Sleeps 8
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Eagles Nest - Lakefront Contemporary Home 3200 Sq' w Piano - 5 Queen Beds, holiday rental in Highland Falls

Eagles Nest - Lakefront Contemporary Home 3200 Sq' w Piano - 5 Queen Beds

4 bedrooms
3 bathrooms
Sleeps 10
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Bear Mountain House., holiday rental in Highland Falls

Bear Mountain House.

3 bedrooms
3 bathrooms
Sleeps 8
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Beautiful Modern House Minutes from Main Street, holiday rental in Highland Falls

Beautiful Modern House Minutes from Main Street

3 bedrooms
3 bathrooms
Sleeps 6
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Our Rockbound Highland Home * 2 Blocks to West Point * 1/2 Block to Main St, holiday rental in Highland Falls

Our Rockbound Highland Home * 2 Blocks to West Point * 1/2 Block to Main St

3 bedrooms
2 bathrooms
Sleeps 10
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Stay at Sparrow House: A Cozy, Waterfront Retreat in the Hudson Valley, holiday rental in Highland Falls

Stay at Sparrow House: A Cozy, Waterfront Retreat in the Hudson Valley

4 bedrooms
2 bathrooms
Sleeps 10
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Holiday cozy country cottage!, holiday rental in Highland Falls

Holiday cozy country cottage!

4 bedrooms
2 bathrooms
Sleeps 7
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50 Mins from  Manhattan River view, holiday rental in Highland Falls

50 Mins from Manhattan River view

5 bedrooms
3 bathrooms
Sleeps 17
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The Famous Hudson Valley Castle W/ Jacuzzi- 8 Min West Point, holiday rental in Highland Falls

The Famous Hudson Valley Castle W/ Jacuzzi- 8 Min West Point

8 bedrooms
6 bathrooms
Sleeps 16
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Storm King Lodge is a country retreat ready for you., holiday rental in Highland Falls

Storm King Lodge is a country retreat ready for you.

4 bedrooms
4 bathrooms
Sleeps 10
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Croton Lodge: Luxury 2bd⭐Comfort+Style⭐45min to NYC., holiday rental in Highland Falls

Croton Lodge: Luxury 2bd⭐Comfort+Style⭐45min to NYC.

2 bedrooms
1 bathroom
Sleeps 6
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Caren House Bed and Breafast, holiday rental in Highland Falls

Caren House Bed and Breafast

3 bedrooms
3 bathrooms
Sleeps 6
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Beautiful modernist home with amazing views, holiday rental in Highland Falls

Beautiful modernist home with amazing views

3 bedrooms
2 bathrooms
Sleeps 6
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Cozy Lake Front House w. Pool near Storm King and West Point, holiday rental in Highland Falls

Cozy Lake Front House w. Pool near Storm King and West Point

4 bedrooms
3 bathrooms
Sleeps 10
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Secluded Lakefront Cottage near Hudson Valley, holiday rental in Highland Falls

Secluded Lakefront Cottage near Hudson Valley

1 bedroom
1 bathroom
Sleeps 4
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Base Camp - Dutch Colonial Estate, holiday rental in Highland Falls

Base Camp - Dutch Colonial Estate

1 bedroom
1 bathroom
Sleeps 2
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Faces The Hudson + Only An Hour Outside NYC, holiday rental in Highland Falls

Faces The Hudson + Only An Hour Outside NYC

3 bedrooms
4 bathrooms
Sleeps 8
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'THE HILLTOP'-40Mins From NYC- Private Estate, holiday rental in Highland Falls

'THE HILLTOP'-40Mins From NYC- Private Estate

4 bedrooms
4 bathrooms
Sleeps 12
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COZY RETREAT: HOT TUB, POOL, SAUNA, AND MORE..., holiday rental in Highland Falls

COZY RETREAT: HOT TUB, POOL, SAUNA, AND MORE...

5 bedrooms
3 bathrooms
Sleeps 15
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Guests state the home is charming. New central air conditioning., holiday rental in Highland Falls

Guests state the home is charming. New central air conditioning.

1 bedroom
1 bathroom
Sleeps 4
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Enchanting Hudson Valley Cottage Near Hiking!, holiday rental in Highland Falls

Enchanting Hudson Valley Cottage Near Hiking!

3 bedrooms
2 bathrooms
Sleeps 5
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Tentrr - Cooke's Creek, holiday rental in Highland Falls

Tentrr - Cooke's Creek

1 bedroom
1 bathroom
Sleeps 4
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Tentrr Signature Site - Downing Wood, holiday rental in Highland Falls

Tentrr Signature Site - Downing Wood

1 bedroom
1 bathroom
Sleeps 4
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Beautiful Private House; Golf, Hike, Fish, Swim, Relax, holiday rental in Highland Falls

Beautiful Private House; Golf, Hike, Fish, Swim, Relax

2 bedrooms
4 bathrooms
Sleeps 6
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A Destination for All Seasons, holiday rental in Highland Falls

A Destination for All Seasons

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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DOMIR Garrison log cabin +hot tub+barrel sauna, holiday rental in Highland Falls

DOMIR Garrison log cabin +hot tub+barrel sauna

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Eagles Nest - Lakefront Contemporary Home 3200 Sq' w Piano - 5 Queen Beds, holiday rental in Highland Falls

Eagles Nest - Lakefront Contemporary Home 3200 Sq' w Piano - 5 Queen Beds

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Huge new modern house with movie theater, holiday rental in Highland Falls

Huge new modern house with movie theater

4 bedrooms
4 bathrooms
Sleeps 8
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Tentrr Signature Site - Two Fields Farm   Close to NYC with beautiful pond, holiday rental in Highland Falls

Tentrr Signature Site - Two Fields Farm Close to NYC with beautiful pond

1 bedroom
1 bathroom
Sleeps 6
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Midcentury Modern House with Stunning Views, holiday rental in Highland Falls

Midcentury Modern House with Stunning Views

3 bedrooms
2 bathrooms
Sleeps 8
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Beautiful house, Woodbury comns SKI NYC 55 Miles

0 bedrooms
0 bathrooms
Sleeps 0
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Sunset Manor, holiday rental in Highland Falls

Sunset Manor

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Tentrr State Park Site - NY Harriman State Park - Midway at Silver Mine Lake, holiday rental in Highland Falls

Tentrr State Park Site - NY Harriman State Park - Midway at Silver Mine Lake

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr State Park Site - NY Harriman State Park - Tucked Away at Silver Mine, holiday rental in Highland Falls

Tentrr State Park Site - NY Harriman State Park - Tucked Away at Silver Mine

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr State Park Site - NY Harriman State Park - Field of Five H for Large, holiday rental in Highland Falls

Tentrr State Park Site - NY Harriman State Park - Field of Five H for Large

1 bedroom
1 bathroom
Sleeps 20
Match: Sleeps
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Tentrr State Park Site - NY Harriman State Park - Beaver Dam Silver Mine Lake, holiday rental in Highland Falls

Tentrr State Park Site - NY Harriman State Park - Beaver Dam Silver Mine Lake

1 bedroom
1 bathroom
Sleeps 4
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Modern NY Home w/ Views By Hudson Valley Hiking!, holiday rental in Highland Falls

Modern NY Home w/ Views By Hudson Valley Hiking!

5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Tentrr Signature Site - Pastoral Paradise on 42-Acre Farm Close to NYC, holiday rental in Highland Falls

Tentrr Signature Site - Pastoral Paradise on 42-Acre Farm Close to NYC

1 bedroom
1 bathroom
Sleeps 6
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NEW! Beacon Apt w/ Patio + Grill; Walk to Main St!, holiday rental in Highland Falls

NEW! Beacon Apt w/ Patio + Grill; Walk to Main St!

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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NEW! Bright + Artsy Beacon Abode; Walk to Main St!, holiday rental in Highland Falls

NEW! Bright + Artsy Beacon Abode; Walk to Main St!

1 bedroom
2 bathrooms
Sleeps 8
Match: Sleeps
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NEW! Private Upstairs Unit < 1 Mi to Main Street, holiday rental in Highland Falls

NEW! Private Upstairs Unit < 1 Mi to Main Street

1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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NEW! Private Unit in Peaceful Ossining Suburbs, holiday rental in Highland Falls

NEW! Private Unit in Peaceful Ossining Suburbs

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Rustic Countryside Cottage w/ Spa/Fire Pit/Wood Pellet Stove, holiday rental in Highland Falls

Rustic Countryside Cottage w/ Spa/Fire Pit/Wood Pellet Stove

2 bedrooms
1 bathroom
Sleeps 7
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