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Highland Mills Holiday Rentals

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50 rentals in Highland Mills.
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A Destination for All Seasons, holiday rental in Highland Mills

A Destination for All Seasons

4 bedrooms
5 bathrooms
Sleeps 8
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Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View, holiday rental in Highland Mills

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 Mills

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 Mills

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

3 bedrooms
3 bathrooms
Sleeps 12
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Country getaway with spectacular pond and mountain views, holiday rental in Highland Mills

Country getaway with spectacular pond and mountain views

3 bedrooms
2 bathrooms
Sleeps 6
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Cozy Cottage minutes to West Point, holiday rental in Highland Mills

Cozy Cottage minutes to West Point

3 bedrooms
3 bathrooms
Sleeps 8
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Luxury Apt Sugar Loaf, Near Warwick, holiday rental in Highland Mills

Luxury Apt Sugar Loaf, Near Warwick

2 bedrooms
2 bathrooms
Sleeps 6
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Beautiful 1850's brick farm house in Beacon - 4 bdrm, 2 1/2 bath, entire house., holiday rental in Highland Mills

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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West Point - Bear Mountain - Woodbury Commons, holiday rental in Highland Mills

West Point - Bear Mountain - Woodbury Commons

3 bedrooms
1 bathroom
Sleeps 7
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Historic Barn 2 Bedroom Apartment - Racetrack View, holiday rental in Highland Mills

Historic Barn 2 Bedroom Apartment - Racetrack View

2 bedrooms
1 bathroom
Sleeps 6
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Bear Mountain House., holiday rental in Highland Mills

Bear Mountain House.

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

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 Mills

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 Mills

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

4 bedrooms
2 bathrooms
Sleeps 12
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50 Mins from  Manhattan River view, holiday rental in Highland Mills

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 Mills

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 Mills

Storm King Lodge is a country retreat ready for you.

4 bedrooms
4 bathrooms
Sleeps 10
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Colonial Style 'Warwick Retreat' - 1 Hour to NYC!, holiday rental in Highland Mills

Colonial Style 'Warwick Retreat' - 1 Hour to NYC!

4 bedrooms
3 bathrooms
Sleeps 10
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Caren House Bed and Breafast, holiday rental in Highland Mills

Caren House Bed and Breafast

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

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

4 bedrooms
3 bathrooms
Sleeps 10
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Faces The Hudson + Only An Hour Outside NYC, holiday rental in Highland Mills

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 Mills

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

4 bedrooms
4 bathrooms
Sleeps 12
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The Cottage at Millpond Falls - Warwick NY B&B, holiday rental in Highland Mills

The Cottage at Millpond Falls - Warwick NY B&B

1 bedroom
1 bathroom
Sleeps 2
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COZY RETREAT: HOT TUB, POOL, SAUNA, AND MORE..., holiday rental in Highland Mills

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 Mills

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 Mills

Enchanting Hudson Valley Cottage Near Hiking!

3 bedrooms
2 bathrooms
Sleeps 5
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Tentrr Signature Site - Downing Wood, holiday rental in Highland Mills

Tentrr Signature Site - Downing Wood

1 bedroom
1 bathroom
Sleeps 4
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DOMIR Garrison log cabin +hot tub+barrel sauna, holiday rental in Highland Mills

DOMIR Garrison log cabin +hot tub+barrel sauna

2 bedrooms
2 bathrooms
Sleeps 10
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Huge new modern house with movie theater, holiday rental in Highland Mills

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 Mills

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

1 bedroom
1 bathroom
Sleeps 6
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Beautiful house, Woodbury comns SKI NYC 55 Miles

0 bedrooms
0 bathrooms
Sleeps 0
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NEW! Dtwn Goshen Escape: 1 Block to Historic Track, holiday rental in Highland Mills

NEW! Dtwn Goshen Escape: 1 Block to Historic Track

2 bedrooms
1 bathroom
Sleeps 4
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NEW! Dtwn Goshen Retreat: 29 Mi to Holiday Mtn Ski, holiday rental in Highland Mills

NEW! Dtwn Goshen Retreat: 29 Mi to Holiday Mtn Ski

3 bedrooms
1 bathroom
Sleeps 5
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NEW! Romantic Goshen Getaway: Wineries + Shopping!, holiday rental in Highland Mills

NEW! Romantic Goshen Getaway: Wineries + Shopping!

1 bedroom
1 bathroom
Sleeps 2
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Tentrr State Park Site - NY Harriman State Park - Old Sebago Beach at Lake, holiday rental in Highland Mills

Tentrr State Park Site - NY Harriman State Park - Old Sebago Beach at Lake

1 bedroom
1 bathroom
Sleeps 4
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Tentrr State Park Site - NY Harriman State Park - Midway at Silver Mine Lake, holiday rental in Highland Mills

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

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

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

1 bedroom
1 bathroom
Sleeps 4
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Tentrr State Park Site - NY Harriman State Park - Fenced Field at Lake Sebago, holiday rental in Highland Mills

Tentrr State Park Site - NY Harriman State Park - Fenced Field at Lake Sebago

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

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

1 bedroom
1 bathroom
Sleeps 20
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Tentrr State Park Site - NY Harriman State Park - Water View at Lake Sebago, holiday rental in Highland Mills

Tentrr State Park Site - NY Harriman State Park - Water View at Lake Sebago

1 bedroom
1 bathroom
Sleeps 4
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Tentrr State Park Site - NY Harriman State Park - Old Comfort Station at Lake, holiday rental in Highland Mills

Tentrr State Park Site - NY Harriman State Park - Old Comfort Station at Lake

1 bedroom
1 bathroom
Sleeps 4
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NEW! Updated Home w/ Patio Half Mile to West Point, holiday rental in Highland Mills

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

3 bedrooms
2 bathrooms
Sleeps 6
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Tentrr State Park Site - NY Harriman State Park - Beaver Dam Silver Mine Lake, holiday rental in Highland Mills

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

1 bedroom
1 bathroom
Sleeps 4
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Tentrr Signature Site - Pastoral Paradise on 42-Acre Farm Close to NYC, holiday rental in Highland Mills

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

1 bedroom
1 bathroom
Sleeps 6
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Villa Verde BnB, Greenwood Lake, NY, holiday rental in Highland Mills

Villa Verde BnB, Greenwood Lake, NY

1 bedroom
1 bathroom
Sleeps 2
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NEW! Beacon Apt w/ Patio + Grill; Walk to Main St!, holiday rental in Highland Mills

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

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

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

1 bedroom
2 bathrooms
Sleeps 8
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NEW! Magnificent Chester Villa w/ Pool & Fire Pit, holiday rental in Highland Mills

NEW! Magnificent Chester Villa w/ Pool & Fire Pit

1 bedroom
5 bathrooms
Sleeps 12
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Rustic Countryside Cottage w/ Spa/Fire Pit/Wood Pellet Stove, holiday rental in Highland Mills

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

2 bedrooms
1 bathroom
Sleeps 7
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NEW! Updated Getaway w/ 2 1/2 Private Serene Acres, holiday rental in Highland Mills

NEW! Updated Getaway w/ 2 1/2 Private Serene Acres

3 bedrooms
2 bathrooms
Sleeps 5
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Yes, here are some popular holiday rentals in Highland Mills that have internet access:\n\nSee all holiday rentals in Highland Mills on Tripadvisor