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Highland Holiday Rentals

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50 rentals in Highland.
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Renovated  Cottage in the Heart of Hudson Valley close to Walkway Over Hudson, holiday rental in Highland

Renovated Cottage in the Heart of Hudson Valley close to Walkway Over Hudson

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Secluded Country Getaway, holiday rental in Highland

Secluded Country Getaway

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Hudson Valley Villa - Modern Masterpiece Cantilevered Over Hudson River Bluff, holiday rental in Highland

Hudson Valley Villa - Modern Masterpiece Cantilevered Over Hudson River Bluff

4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Black Creek Bed and Breakfast (Reclaimed Room w/Shared Bathroom), holiday rental in Highland

Black Creek Bed and Breakfast (Reclaimed Room w/Shared Bathroom)

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Unique Hudson Riverfront Home & Pool, holiday rental in Highland

Unique Hudson Riverfront Home & Pool

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Black Creek Bed and Breakfast, holiday rental in Highland

Black Creek Bed and Breakfast

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Black Creek Bed and Breakfast (Arbor Room w/Shared Bathroom), holiday rental in Highland

Black Creek Bed and Breakfast (Arbor Room w/Shared Bathroom)

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Black Creek Bed and Breakfast (Paris Room w/Shared Bathroom), holiday rental in Highland

Black Creek Bed and Breakfast (Paris Room w/Shared Bathroom)

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Black Creek Bed and Breakfast (Zen Room w/Shared Bathroom), holiday rental in Highland

Black Creek Bed and Breakfast (Zen Room w/Shared Bathroom)

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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HUDSON VALLEY! Spectacular Space On a Scenic Mountain~ tons of Family Activities, holiday rental in Highland

HUDSON VALLEY! Spectacular Space On a Scenic Mountain~ tons of Family Activities

5 bedrooms
4 bathrooms
Sleeps 18
Match: Sleeps
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Waterfront Ulster Park Haven with Magnificent Hudson River Views, holiday rental in Highland

Waterfront Ulster Park Haven with Magnificent Hudson River Views

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hudson valley getaway, holiday rental in Highland

Hudson valley getaway

5 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Newly Renovated Hudson Valley 3 Bedroom Home, holiday rental in Highland

Newly Renovated Hudson Valley 3 Bedroom Home

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming Historic Hudson Valley Farmhouse | Close to wineries, hiking, & museums, holiday rental in Highland

Charming Historic Hudson Valley Farmhouse | Close to wineries, hiking, & museums

3 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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GORGEOUS COUNTRY ESTATE, VIEWS, YEAR-ROUND JACUZZI!, holiday rental in Highland

GORGEOUS COUNTRY ESTATE, VIEWS, YEAR-ROUND JACUZZI!

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska, holiday rental in Highland

Hiking/Climbing Paradise- walking distance to Mohonk/Gunks/Minnewaska

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Renovated Schoolhouse - Hudson Valley Getaway, holiday rental in Highland

Renovated Schoolhouse - Hudson Valley Getaway

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Spacious/Secluded Home w/Pool, Chefs Kitchen, Neighboring Farm Pastoral Views., holiday rental in Highland

Spacious/Secluded Home w/Pool, Chefs Kitchen, Neighboring Farm Pastoral Views.

5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Ridge View Walk-up - Close to Mohonk Preserve, Minnewaska, New Paltz & Gardiner, holiday rental in Highland

Ridge View Walk-up - Close to Mohonk Preserve, Minnewaska, New Paltz & Gardiner

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Gorgeous Country Oasis, with pool, pond on a lush 16 acres, holiday rental in Highland

Gorgeous Country Oasis, with pool, pond on a lush 16 acres

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Orchard Keeper's Private Apt. - Entire Second Floor of 1873 Marlboro Farmhouse, holiday rental in Highland

Orchard Keeper's Private Apt. - Entire Second Floor of 1873 Marlboro Farmhouse

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy And Inviting Nestled In The Heart Of Ny Apple Mecca. Easy 5 Min. To Village, holiday rental in Highland

Cozy And Inviting Nestled In The Heart Of Ny Apple Mecca. Easy 5 Min. To Village

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Dutchess County 5 star Luxury Estate . 10 minutes from Rhinebeck, holiday rental in Highland

Dutchess County 5 star Luxury Estate . 10 minutes from Rhinebeck

8 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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1800s Farmhouse set on 165 Acre Estate-- Does not include Caretaker's Apartment, holiday rental in Highland

1800s Farmhouse set on 165 Acre Estate-- Does not include Caretaker's Apartment

3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Lakefront Cottage, Hudson Valley NY, holiday rental in Highland

Lakefront Cottage, Hudson Valley NY

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Harrison Field Peaceful 10Acre Retreat, holiday rental in Highland

Harrison Field Peaceful 10Acre Retreat

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Earth Berm House at Terra Casa Retreat Center, holiday rental in Highland

Earth Berm House at Terra Casa Retreat Center

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Private King Bed w/Bath in SHARED Charming House, good for business travelers, holiday rental in Highland

Private King Bed w/Bath in SHARED Charming House, good for business travelers

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Family Retreat in Rhinebeck with Pool, Newly Renovated, holiday rental in Highland

Family Retreat in Rhinebeck with Pool, Newly Renovated

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Renee's Get-Away New Paltz, holiday rental in Highland

Renee's Get-Away New Paltz

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cozy Apple House, holiday rental in Highland

Cozy Apple House

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The Queen City Cottage, holiday rental in Highland

The Queen City Cottage

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Millbrook Country Dream! Tennis/Swim/Play, holiday rental in Highland

Millbrook Country Dream! Tennis/Swim/Play

3 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Charming Brick House -Hudson Valley, holiday rental in Highland

Charming Brick House -Hudson Valley

3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Dutchess County Guest House on Working Horse Farm!, holiday rental in Highland

Dutchess County Guest House on Working Horse Farm!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Phillie's Country Comfort Space   -, holiday rental in Highland

Phillie's Country Comfort Space -

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Gatehouse Gardens, holiday rental in Highland

Gatehouse Gardens

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Grotto View at Stone Mountain Farm, holiday rental in Highland

Tentrr Signature Site - Grotto View at Stone Mountain Farm

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Kamp Kimberg North, holiday rental in Highland

Tentrr Signature Site - Kamp Kimberg North

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Mini Yosemite in the Hudson Valley, holiday rental in Highland

Tentrr Signature Site - Mini Yosemite in the Hudson Valley

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning Hudson Valley Retreat: Huge Deck w/ views, 7 acres, 90 min from NYC, holiday rental in Highland

Stunning Hudson Valley Retreat: Huge Deck w/ views, 7 acres, 90 min from NYC

4 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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NEW! Secluded Home w/Fire Pit: Sip, Ski & Explore!, holiday rental in Highland

NEW! Secluded Home w/Fire Pit: Sip, Ski & Explore!

6 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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5 Bedroom Rustic Country Home, holiday rental in Highland

5 Bedroom Rustic Country Home

5 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Tentrr Signature Site - Reservoir Retreat, holiday rental in Highland

Tentrr Signature Site - Reservoir Retreat

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Rifton Farm Hidden Forest, holiday rental in Highland

Tentrr Signature Site - Rifton Farm Hidden Forest

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Midcentury Modern House with Stunning Views, holiday rental in Highland

Midcentury Modern House with Stunning Views

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy Hudson Valley 1880 Carriage House with FIRE PLACE, holiday rental in Highland

Cozy Hudson Valley 1880 Carriage House with FIRE PLACE

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Famous Liberty View Farm, holiday rental in Highland

Famous Liberty View Farm

3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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NEW! Enchanting Hudson Valley Farmhouse w/ Views!, holiday rental in Highland

NEW! Enchanting Hudson Valley Farmhouse w/ Views!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Modern, Luxury Vintage CAMPER with Swimming Pool in the Hudson Valley, holiday rental in Highland

Modern, Luxury Vintage CAMPER with Swimming Pool in the Hudson Valley

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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