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Highland Mills Vacation Rentals

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Bedrooms

Bathrooms

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Distinctive Features

29 rentals in Highland Mills.
Orchard Hill Estate -Under 1 hr NYC-PETS Welcome-Hot Tub-Pool-Fire Pit-Private, vacation rental in Highland Mills
Orchard Hill Estate -Under 1 hr NYC-PETS Welcome-Hot Tub-Pool-Fire Pit-Private, vacation rental in Highland Mills
Orchard Hill Estate -Under 1 hr NYC-PETS Welcome-Hot Tub-Pool-Fire Pit-Private, vacation rental in Highland Mills

Orchard Hill Estate -Under 1 hr NYC-PETS Welcome-Hot Tub-Pool-Fire Pit-Private

Rental Home
8 bedrooms
5 bathrooms
Sleeps 25
Match: Sleeps
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Country Bliss LAKE HOME -  Relax into Nature Enjoying Year Round Wonders., vacation rental in Highland Mills
Country Bliss LAKE HOME -  Relax into Nature Enjoying Year Round Wonders., vacation rental in Highland Mills
Country Bliss LAKE HOME -  Relax into Nature Enjoying Year Round Wonders., vacation rental in Highland Mills

Country Bliss LAKE HOME - Relax into Nature Enjoying Year Round Wonders.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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NATURE'S NIRVANA FOR FAMILY AND FRIEND, vacation rental in Highland Mills
NATURE'S NIRVANA FOR FAMILY AND FRIEND, vacation rental in Highland Mills
NATURE'S NIRVANA FOR FAMILY AND FRIEND, vacation rental in Highland Mills

NATURE'S NIRVANA FOR FAMILY AND FRIEND

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Hudson Valley Getaway! Private Pool, Hot Tub, & Sauna! 1HR from NYC, vacation rental in Highland Mills
Hudson Valley Getaway! Private Pool, Hot Tub, & Sauna! 1HR from NYC, vacation rental in Highland Mills
Hudson Valley Getaway! Private Pool, Hot Tub, & Sauna! 1HR from NYC, vacation rental in Highland Mills

Hudson Valley Getaway! Private Pool, Hot Tub, & Sauna! 1HR from NYC

Rental Home
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful 2 Bedroom Cottage with On-Site Parking, vacation rental in Highland Mills
Beautiful 2 Bedroom Cottage with On-Site Parking, vacation rental in Highland Mills
Beautiful 2 Bedroom Cottage with On-Site Parking, vacation rental in Highland Mills

Beautiful 2 Bedroom Cottage with On-Site Parking

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Storm King Lodge is a country retreat ready for you., vacation rental in Highland Mills
Storm King Lodge is a country retreat ready for you., vacation rental in Highland Mills
Storm King Lodge is a country retreat ready for you., vacation rental in Highland Mills

Storm King Lodge is a country retreat ready for you.

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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New Construction Mountain house perfect winter getaway near skilling, vacation rental in Highland Mills
New Construction Mountain house perfect winter getaway near skilling, vacation rental in Highland Mills
New Construction Mountain house perfect winter getaway near skilling, vacation rental in Highland Mills

New Construction Mountain house perfect winter getaway near skilling

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lakefront Getaway w/ Mix of Cozy & Modern Touches, vacation rental in Highland Mills
Lakefront Getaway w/ Mix of Cozy & Modern Touches, vacation rental in Highland Mills
Lakefront Getaway w/ Mix of Cozy & Modern Touches, vacation rental in Highland Mills

Lakefront Getaway w/ Mix of Cozy & Modern Touches

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Caren House Bed and Breafast, vacation rental in Highland Mills
Caren House Bed and Breafast, vacation rental in Highland Mills
Caren House Bed and Breafast, vacation rental in Highland Mills

Caren House Bed and Breafast

Private Room
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful, Secluded, Country Cottage, With 30x60 In-Ground Pool., vacation rental in Highland Mills
Beautiful, Secluded, Country Cottage, With 30x60 In-Ground Pool., vacation rental in Highland Mills
Beautiful, Secluded, Country Cottage, With 30x60 In-Ground Pool., vacation rental in Highland Mills

Beautiful, Secluded, Country Cottage, With 30x60 In-Ground Pool.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Huge home for huge fun – NY fun!, vacation rental in Highland Mills
Huge home for huge fun – NY fun!, vacation rental in Highland Mills
Huge home for huge fun – NY fun!, vacation rental in Highland Mills

Huge home for huge fun – NY fun!

Rental Home
7 bedrooms
4 bathrooms
Sleeps 17
Match: Sleeps
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NEW- Lake Lodge 35 miles to NYC w 2ooft LakeFront, vacation rental in Highland Mills
NEW- Lake Lodge 35 miles to NYC w 2ooft LakeFront, vacation rental in Highland Mills
NEW- Lake Lodge 35 miles to NYC w 2ooft LakeFront, vacation rental in Highland Mills

NEW- Lake Lodge 35 miles to NYC w 2ooft LakeFront

Rental Home
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Charming Swedish Cottage in the Woods - Washingtonville & West Point, vacation rental in Highland Mills
Charming Swedish Cottage in the Woods - Washingtonville & West Point, vacation rental in Highland Mills
Charming Swedish Cottage in the Woods - Washingtonville & West Point, vacation rental in Highland Mills

Charming Swedish Cottage in the Woods - Washingtonville & West Point

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious Colonial on 2 plus  Acres, vacation rental in Highland Mills
Spacious Colonial on 2 plus  Acres, vacation rental in Highland Mills
Spacious Colonial on 2 plus  Acres, vacation rental in Highland Mills

Spacious Colonial on 2 plus Acres

Rental Home
4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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A hidden creek in Monroe, vacation rental in Highland Mills
A hidden creek in Monroe, vacation rental in Highland Mills
A hidden creek in Monroe, vacation rental in Highland Mills

A hidden creek in Monroe

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cozy Family Home Near West Point,  Shopping,  Skiing and Legoland, vacation rental in Highland Mills
Cozy Family Home Near West Point,  Shopping,  Skiing and Legoland, vacation rental in Highland Mills
Cozy Family Home Near West Point,  Shopping,  Skiing and Legoland, vacation rental in Highland Mills

Cozy Family Home Near West Point, Shopping, Skiing and Legoland

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Hudson Valley Sunset House - Grill | Fire Pit | Hiking, vacation rental in Highland Mills
Hudson Valley Sunset House - Grill | Fire Pit | Hiking, vacation rental in Highland Mills
Hudson Valley Sunset House - Grill | Fire Pit | Hiking, vacation rental in Highland Mills

Hudson Valley Sunset House - Grill | Fire Pit | Hiking

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Close to West Point travelers lounge, vacation rental in Highland Mills
Close to West Point travelers lounge, vacation rental in Highland Mills
Close to West Point travelers lounge, vacation rental in Highland Mills

Close to West Point travelers lounge

Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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NEW- 2 Side by Side MODERN Lake Houses - 35 miles from NY, vacation rental in Highland Mills
NEW- 2 Side by Side MODERN Lake Houses - 35 miles from NY, vacation rental in Highland Mills
NEW- 2 Side by Side MODERN Lake Houses - 35 miles from NY, vacation rental in Highland Mills

NEW- 2 Side by Side MODERN Lake Houses - 35 miles from NY

Rental Home
6 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Kick back & relax in this peaceful, stylish place to stay with the whole family., vacation rental in Highland Mills
Kick back & relax in this peaceful, stylish place to stay with the whole family., vacation rental in Highland Mills
Kick back & relax in this peaceful, stylish place to stay with the whole family., vacation rental in Highland Mills

Kick back & relax in this peaceful, stylish place to stay with the whole family.

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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�Cozy Lakefront Cabin�, vacation rental in Highland Mills
�Cozy Lakefront Cabin�, vacation rental in Highland Mills
�Cozy Lakefront Cabin�, vacation rental in Highland Mills

�Cozy Lakefront Cabin�

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Upstate NY getaway- View, Pool, Close to Woodbury Common, vacation rental in Highland Mills
Upstate NY getaway- View, Pool, Close to Woodbury Common, vacation rental in Highland Mills
Upstate NY getaway- View, Pool, Close to Woodbury Common, vacation rental in Highland Mills

Upstate NY getaway- View, Pool, Close to Woodbury Common

Rental Home
2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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One-of-a-kind 5BR cottage, vacation rental in Highland Mills
One-of-a-kind 5BR cottage, vacation rental in Highland Mills
One-of-a-kind 5BR cottage, vacation rental in Highland Mills

One-of-a-kind 5BR cottage

Rental Home
5 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
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Awesome Country Retreat - 5BR - Private and Peaceful, vacation rental in Highland Mills
Awesome Country Retreat - 5BR - Private and Peaceful, vacation rental in Highland Mills
Awesome Country Retreat - 5BR - Private and Peaceful, vacation rental in Highland Mills

Awesome Country Retreat - 5BR - Private and Peaceful

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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The Twin Lakes House - Lake view, vacation rental in Highland Mills
The Twin Lakes House - Lake view, vacation rental in Highland Mills
The Twin Lakes House - Lake view, vacation rental in Highland Mills

The Twin Lakes House - Lake view

Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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★ NEW ★ Charming 3BR 3Bath In Briliant Location!, vacation rental in Highland Mills
★ NEW ★ Charming 3BR 3Bath In Briliant Location!, vacation rental in Highland Mills
★ NEW ★ Charming 3BR 3Bath In Briliant Location!, vacation rental in Highland Mills

★ NEW ★ Charming 3BR 3Bath In Briliant Location!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Incredible Ranch in the Woods - Peace and Luxury!, vacation rental in Highland Mills
Incredible Ranch in the Woods - Peace and Luxury!, vacation rental in Highland Mills
Incredible Ranch in the Woods - Peace and Luxury!, vacation rental in Highland Mills

Incredible Ranch in the Woods - Peace and Luxury!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Stunning, Private House in the Hills - Huge Pool!, vacation rental in Highland Mills
Stunning, Private House in the Hills - Huge Pool!, vacation rental in Highland Mills
Stunning, Private House in the Hills - Huge Pool!, vacation rental in Highland Mills

Stunning, Private House in the Hills - Huge Pool!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Mid-Hudson Estate: 11 acres, Pool, 1 hr to NYC, vacation rental in Highland Mills
Mid-Hudson Estate: 11 acres, Pool, 1 hr to NYC, vacation rental in Highland Mills
Mid-Hudson Estate: 11 acres, Pool, 1 hr to NYC, vacation rental in Highland Mills

Mid-Hudson Estate: 11 acres, Pool, 1 hr to NYC

Rental Home
8 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Showing results 1-29 of 29