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Highland Falls Vacation Rentals

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50 rentals in Highland Falls.
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Our Rockbound Highland Home * 2 Blocks from Thayer Gate  * 1/2 Block to Main St., vacation rental in Highland Falls
Our Rockbound Highland Home * 2 Blocks from Thayer Gate  * 1/2 Block to Main St., vacation rental in Highland Falls
Our Rockbound Highland Home * 2 Blocks from Thayer Gate  * 1/2 Block to Main St., vacation rental in Highland Falls

Our Rockbound Highland Home * 2 Blocks from Thayer Gate * 1/2 Block to Main St.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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SEM-PVT APT NEXT TO WEST POINT & BEAR MT STATE PARK; LESS THAN 50 MILES TO NYC, vacation rental in Highland Falls
SEM-PVT APT NEXT TO WEST POINT & BEAR MT STATE PARK; LESS THAN 50 MILES TO NYC, vacation rental in Highland Falls
SEM-PVT APT NEXT TO WEST POINT & BEAR MT STATE PARK; LESS THAN 50 MILES TO NYC, vacation rental in Highland Falls

SEM-PVT APT NEXT TO WEST POINT & BEAR MT STATE PARK; LESS THAN 50 MILES TO NYC

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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West Point - Bear Mountain - Woodbury Commons, vacation rental in Highland Falls
West Point - Bear Mountain - Woodbury Commons, vacation rental in Highland Falls
West Point - Bear Mountain - Woodbury Commons, vacation rental in Highland Falls

West Point - Bear Mountain - Woodbury Commons

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

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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West Point - River View Apt within Home - 1 mile from Thayer Gate, vacation rental in Highland Falls
West Point - River View Apt within Home - 1 mile from Thayer Gate, vacation rental in Highland Falls
West Point - River View Apt within Home - 1 mile from Thayer Gate, vacation rental in Highland Falls

West Point - River View Apt within Home - 1 mile from Thayer Gate

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Getaway in the HEART of West Point!, vacation rental in Highland Falls
Charming Getaway in the HEART of West Point!, vacation rental in Highland Falls
Charming Getaway in the HEART of West Point!, vacation rental in Highland Falls

Charming Getaway in the HEART of West Point!

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stay on Main Street in West Point! Walk to Academy Gate!, vacation rental in Highland Falls
Stay on Main Street in West Point! Walk to Academy Gate!, vacation rental in Highland Falls
Stay on Main Street in West Point! Walk to Academy Gate!, vacation rental in Highland Falls

Stay on Main Street in West Point! Walk to Academy Gate!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Newly Renovated Home in the Heart of West Point, vacation rental in Highland Falls
Newly Renovated Home in the Heart of West Point, vacation rental in Highland Falls
Newly Renovated Home in the Heart of West Point, vacation rental in Highland Falls

Newly Renovated Home in the Heart of West Point

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Peaceful 3 bedroom house - Free Parking, vacation rental in Highland Falls
Peaceful 3 bedroom house - Free Parking, vacation rental in Highland Falls
Peaceful 3 bedroom house - Free Parking, vacation rental in Highland Falls

Peaceful 3 bedroom house - Free Parking

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Discover Nature’s Glory! Perfect Family Home, vacation rental in Highland Falls
Discover Nature’s Glory! Perfect Family Home, vacation rental in Highland Falls
Discover Nature’s Glory! Perfect Family Home, vacation rental in Highland Falls

Discover Nature’s Glory! Perfect Family Home

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Bear Mountain House., vacation rental in Highland Falls
Bear Mountain House., vacation rental in Highland Falls
Bear Mountain House., vacation rental in Highland Falls

Bear Mountain House.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Our Rockbound Highland Home * 2 Blocks to West Point * 1/2 Block to Main St, vacation rental in Highland Falls
Our Rockbound Highland Home * 2 Blocks to West Point * 1/2 Block to Main St, vacation rental in Highland Falls
Our Rockbound Highland Home * 2 Blocks to West Point * 1/2 Block to Main St, vacation rental in Highland Falls

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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A luxurious retreat in Garrison, NY, vacation rental in Highland Falls
A luxurious retreat in Garrison, NY, vacation rental in Highland Falls
A luxurious retreat in Garrison, NY, vacation rental in Highland Falls

A luxurious retreat in Garrison, NY

Rental Home
4 bedrooms
4 bathrooms
Sleeps 7
Match: Sleeps
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Historic Cold Spring Village House---Walk To Train, vacation rental in Highland Falls
Historic Cold Spring Village House---Walk To Train, vacation rental in Highland Falls
Historic Cold Spring Village House---Walk To Train, vacation rental in Highland Falls

Historic Cold Spring Village House---Walk To Train

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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'The Glabin’: Garrison Gem w/ Deck & Fire Pit!, vacation rental in Highland Falls
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!, vacation rental in Highland Falls
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!, vacation rental in Highland Falls

'The Glabin’: Garrison Gem w/ Deck & Fire Pit!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Woodland Mountain Retreat: Appalachian Trail, Cold Spring, Beacon, West Point!, vacation rental in Highland Falls
Woodland Mountain Retreat: Appalachian Trail, Cold Spring, Beacon, West Point!, vacation rental in Highland Falls
Woodland Mountain Retreat: Appalachian Trail, Cold Spring, Beacon, West Point!, vacation rental in Highland Falls

Woodland Mountain Retreat: Appalachian Trail, Cold Spring, Beacon, West Point!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Downing Wood, vacation rental in Highland Falls
Tentrr Signature Site - Downing Wood, vacation rental in Highland Falls
Tentrr Signature Site - Downing Wood, vacation rental in Highland Falls

Tentrr Signature Site - Downing Wood

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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COZY RETREAT: HOT TUB, POOL, SAUNA, AND MORE..., vacation rental in Highland Falls
COZY RETREAT: HOT TUB, POOL, SAUNA, AND MORE..., vacation rental in Highland Falls
COZY RETREAT: HOT TUB, POOL, SAUNA, AND MORE..., vacation rental in Highland Falls

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Tentrr Signature Site - Downing Wood, vacation rental in Highland Falls
Tentrr Signature Site - Downing Wood, vacation rental in Highland Falls
Tentrr Signature Site - Downing Wood, vacation rental in Highland Falls

Tentrr Signature Site - Downing Wood

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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DOMIR Garrison log cabin +hot tub+barrel sauna, vacation rental in Highland Falls
DOMIR Garrison log cabin +hot tub+barrel sauna, vacation rental in Highland Falls
DOMIR Garrison log cabin +hot tub+barrel sauna, vacation rental in Highland Falls

DOMIR Garrison log cabin +hot tub+barrel sauna

Rental Home
2 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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DOMIR  Garrison log cabin with new spa hot tub 
and sauna, vacation rental in Highland Falls
DOMIR  Garrison log cabin with new spa hot tub 
and sauna, vacation rental in Highland Falls
DOMIR  Garrison log cabin with new spa hot tub 
and sauna, vacation rental in Highland Falls

DOMIR Garrison log cabin with new spa hot tub and sauna

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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COZY RETREAT : HOT TUB, SAUNA, FULL GYM, POOL + MORE, vacation rental in Highland Falls
COZY RETREAT : HOT TUB, SAUNA, FULL GYM, POOL + MORE, vacation rental in Highland Falls
COZY RETREAT : HOT TUB, SAUNA, FULL GYM, POOL + MORE, vacation rental in Highland Falls

COZY RETREAT : HOT TUB, SAUNA, FULL GYM, POOL + MORE

Rental Home
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
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Mountain lake lodge., vacation rental in Highland Falls
Mountain lake lodge., vacation rental in Highland Falls
Mountain lake lodge., vacation rental in Highland Falls

Mountain lake lodge.

Rental Home
3 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Eco-Friendly Luxury Hikers' Retreat, vacation rental in Highland Falls
Eco-Friendly Luxury Hikers' Retreat, vacation rental in Highland Falls
Eco-Friendly Luxury Hikers' Retreat, vacation rental in Highland Falls

Eco-Friendly Luxury Hikers' Retreat

Rental Home
5 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
More info
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Modern Luxurious Country Retreat 1hr from NYC, vacation rental in Highland Falls
Modern Luxurious Country Retreat 1hr from NYC, vacation rental in Highland Falls
Modern Luxurious Country Retreat 1hr from NYC, vacation rental in Highland Falls

Modern Luxurious Country Retreat 1hr from NYC

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Hudson Valley Heaven | a wooded oasis with modern amenities awaits you, vacation rental in Highland Falls
Hudson Valley Heaven | a wooded oasis with modern amenities awaits you, vacation rental in Highland Falls
Hudson Valley Heaven | a wooded oasis with modern amenities awaits you, vacation rental in Highland Falls

Hudson Valley Heaven | a wooded oasis with modern amenities awaits you

Rental Home
5 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps
More info
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Swimming in the hudson highlands in your own super private woodland sanctuary., vacation rental in Highland Falls
Swimming in the hudson highlands in your own super private woodland sanctuary., vacation rental in Highland Falls
Swimming in the hudson highlands in your own super private woodland sanctuary., vacation rental in Highland Falls

Swimming in the hudson highlands in your own super private woodland sanctuary.

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Castle by the Lake, vacation rental in Highland Falls
Castle by the Lake, vacation rental in Highland Falls
Castle by the Lake, vacation rental in Highland Falls

Castle by the Lake

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Relax and Unwind! Free Parking, Pet-friendly Property, Outdoor Pool, vacation rental in Highland Falls
Relax and Unwind! Free Parking, Pet-friendly Property, Outdoor Pool, vacation rental in Highland Falls
Relax and Unwind! Free Parking, Pet-friendly Property, Outdoor Pool, vacation rental in Highland Falls

Relax and Unwind! Free Parking, Pet-friendly Property, Outdoor Pool

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Modern & secluded with a private outdoor hot tub and sauna!, vacation rental in Highland Falls
Modern & secluded with a private outdoor hot tub and sauna!, vacation rental in Highland Falls
Modern & secluded with a private outdoor hot tub and sauna!, vacation rental in Highland Falls

Modern & secluded with a private outdoor hot tub and sauna!

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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☀️ Summer 4BR Center Cold Spring NY, vacation rental in Highland Falls
☀️ Summer 4BR Center Cold Spring NY, vacation rental in Highland Falls
☀️ Summer 4BR Center Cold Spring NY, vacation rental in Highland Falls

☀️ Summer 4BR Center Cold Spring NY

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Eco-Friendly Resort in the Mountain Cabin! 3 Great Units, Free Parking, Pool, vacation rental in Highland Falls
Eco-Friendly Resort in the Mountain Cabin! 3 Great Units, Free Parking, Pool, vacation rental in Highland Falls
Eco-Friendly Resort in the Mountain Cabin! 3 Great Units, Free Parking, Pool, vacation rental in Highland Falls

Eco-Friendly Resort in the Mountain Cabin! 3 Great Units, Free Parking, Pool

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Comfort and Convenience! 2 Great Units, Pets Allowed, Free parking, Onsite Pool, vacation rental in Highland Falls
Comfort and Convenience! 2 Great Units, Pets Allowed, Free parking, Onsite Pool, vacation rental in Highland Falls
Comfort and Convenience! 2 Great Units, Pets Allowed, Free parking, Onsite Pool, vacation rental in Highland Falls

Comfort and Convenience! 2 Great Units, Pets Allowed, Free parking, Onsite Pool

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Your Home Away From Home! Free Parking, Onsite Pool, Near Bear Mountain Bridge, vacation rental in Highland Falls
Your Home Away From Home! Free Parking, Onsite Pool, Near Bear Mountain Bridge, vacation rental in Highland Falls
Your Home Away From Home! Free Parking, Onsite Pool, Near Bear Mountain Bridge, vacation rental in Highland Falls

Your Home Away From Home! Free Parking, Onsite Pool, Near Bear Mountain Bridge

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Enjoy Sunsets at the resort in Mountain Cabin! Near Bear Mountain State Park, vacation rental in Highland Falls
Enjoy Sunsets at the resort in Mountain Cabin! Near Bear Mountain State Park, vacation rental in Highland Falls
Enjoy Sunsets at the resort in Mountain Cabin! Near Bear Mountain State Park, vacation rental in Highland Falls

Enjoy Sunsets at the resort in Mountain Cabin! Near Bear Mountain State Park

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Your Home Away From Home! 3 Comfortable Units, Free Parking, Pets Allowed, vacation rental in Highland Falls
Your Home Away From Home! 3 Comfortable Units, Free Parking, Pets Allowed, vacation rental in Highland Falls
Your Home Away From Home! 3 Comfortable Units, Free Parking, Pets Allowed, vacation rental in Highland Falls

Your Home Away From Home! 3 Comfortable Units, Free Parking, Pets Allowed

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Great Relaxing Overnight Stay! Free Parking, Pool, Near Bear Mountain State Park, vacation rental in Highland Falls
Great Relaxing Overnight Stay! Free Parking, Pool, Near Bear Mountain State Park, vacation rental in Highland Falls
Great Relaxing Overnight Stay! Free Parking, Pool, Near Bear Mountain State Park, vacation rental in Highland Falls

Great Relaxing Overnight Stay! Free Parking, Pool, Near Bear Mountain State Park

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Relax and Unwind! 2 Classy Units, Free Parking, Near Bear Mountain State Park, vacation rental in Highland Falls
Relax and Unwind! 2 Classy Units, Free Parking, Near Bear Mountain State Park, vacation rental in Highland Falls
Relax and Unwind! 2 Classy Units, Free Parking, Near Bear Mountain State Park, vacation rental in Highland Falls

Relax and Unwind! 2 Classy Units, Free Parking, Near Bear Mountain State Park

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Cozy Private Apartment in 1820's Hudson Valley Cottage, vacation rental in Highland Falls
Cozy Private Apartment in 1820's Hudson Valley Cottage, vacation rental in Highland Falls
Cozy Private Apartment in 1820's Hudson Valley Cottage, vacation rental in Highland Falls

Cozy Private Apartment in 1820's Hudson Valley Cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Explore Cultural Resorts! 4 Classy Unit, Pool, Near Bear Mountain State Park, vacation rental in Highland Falls
Explore Cultural Resorts! 4 Classy Unit, Pool, Near Bear Mountain State Park, vacation rental in Highland Falls
Explore Cultural Resorts! 4 Classy Unit, Pool, Near Bear Mountain State Park, vacation rental in Highland Falls

Explore Cultural Resorts! 4 Classy Unit, Pool, Near Bear Mountain State Park

Rental Home
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
More info
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Pleasant Stay, Convenient Location! 2 Comfortable Units, Free Parking, Pool, vacation rental in Highland Falls
Pleasant Stay, Convenient Location! 2 Comfortable Units, Free Parking, Pool, vacation rental in Highland Falls
Pleasant Stay, Convenient Location! 2 Comfortable Units, Free Parking, Pool, vacation rental in Highland Falls

Pleasant Stay, Convenient Location! 2 Comfortable Units, Free Parking, Pool

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Convenient Stay, Superb Location! 4 Great Units, Free Parking, Pets Allowed, vacation rental in Highland Falls
Convenient Stay, Superb Location! 4 Great Units, Free Parking, Pets Allowed, vacation rental in Highland Falls
Convenient Stay, Superb Location! 4 Great Units, Free Parking, Pets Allowed, vacation rental in Highland Falls

Convenient Stay, Superb Location! 4 Great Units, Free Parking, Pets Allowed

Rental Home
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Exotic Adventure in a Mountain Cabin! 4 Great Units, Free Parking, Pets Allowed, vacation rental in Highland Falls
Exotic Adventure in a Mountain Cabin! 4 Great Units, Free Parking, Pets Allowed, vacation rental in Highland Falls
Exotic Adventure in a Mountain Cabin! 4 Great Units, Free Parking, Pets Allowed, vacation rental in Highland Falls

Exotic Adventure in a Mountain Cabin! 4 Great Units, Free Parking, Pets Allowed

Rental Home
4 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
More info
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Relax and Unwind! Pool, Free Parking, Visit Woodbury Common Premium Outlets, vacation rental in Highland Falls
Relax and Unwind! Pool, Free Parking, Visit Woodbury Common Premium Outlets, vacation rental in Highland Falls
Relax and Unwind! Pool, Free Parking, Visit Woodbury Common Premium Outlets, vacation rental in Highland Falls

Relax and Unwind! Pool, Free Parking, Visit Woodbury Common Premium Outlets

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Countryside Barn/Garage Loft w Spa/Enclosed Yard/Fire Pit/Pellet Stove, vacation rental in Highland Falls
Cozy Countryside Barn/Garage Loft w Spa/Enclosed Yard/Fire Pit/Pellet Stove, vacation rental in Highland Falls
Cozy Countryside Barn/Garage Loft w Spa/Enclosed Yard/Fire Pit/Pellet Stove, vacation rental in Highland Falls

Cozy Countryside Barn/Garage Loft w Spa/Enclosed Yard/Fire Pit/Pellet Stove

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Prime Location! 3 Pet-friendly Units, Free Parking, Onsite Swimming Pool, vacation rental in Highland Falls
Prime Location! 3 Pet-friendly Units, Free Parking, Onsite Swimming Pool, vacation rental in Highland Falls
Prime Location! 3 Pet-friendly Units, Free Parking, Onsite Swimming Pool, vacation rental in Highland Falls

Prime Location! 3 Pet-friendly Units, Free Parking, Onsite Swimming Pool

Rental Home
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Enjoy the Rustic Elegance in Mountain Cabin with Breathtaking Lake Views, vacation rental in Highland Falls
Enjoy the Rustic Elegance in Mountain Cabin with Breathtaking Lake Views, vacation rental in Highland Falls
Enjoy the Rustic Elegance in Mountain Cabin with Breathtaking Lake Views, vacation rental in Highland Falls

Enjoy the Rustic Elegance in Mountain Cabin with Breathtaking Lake Views

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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New! Hudson Valley Home with River Views near Cold Spring, NY., vacation rental in Highland Falls
New! Hudson Valley Home with River Views near Cold Spring, NY., vacation rental in Highland Falls
New! Hudson Valley Home with River Views near Cold Spring, NY., vacation rental in Highland Falls

New! Hudson Valley Home with River Views near Cold Spring, NY.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Cold spring mtn house, vacation rental in Highland Falls
Cold spring mtn house, vacation rental in Highland Falls
Cold spring mtn house, vacation rental in Highland Falls

Cold spring mtn house

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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West Point Mansion: New York City's Luxury Retreat, vacation rental in Highland Falls
West Point Mansion: New York City's Luxury Retreat, vacation rental in Highland Falls
West Point Mansion: New York City's Luxury Retreat, vacation rental in Highland Falls

West Point Mansion: New York City's Luxury Retreat

Rental Home
7 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
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