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Pine Plains Vacation Rentals

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50 rentals in Pine Plains.
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Elegant Historic Hudson Valley Gilded Age Mansion On 4+ Parklike Acres, vacation rental in Pine Plains

Elegant Historic Hudson Valley Gilded Age Mansion On 4+ Parklike Acres

10 bedrooms
10 bathrooms
Sleeps 22
Match: Sleeps
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Modern Antique Farmhouse in the Hudson Valley, vacation rental in Pine Plains

Modern Antique Farmhouse in the Hudson Valley

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Lakefront Home in Hudson Valley Dutchess County, Pine Plains, New York, vacation rental in Pine Plains

Lakefront Home in Hudson Valley Dutchess County, Pine Plains, New York

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hudson Valley - Picardy Farm: Entire Estate, vacation rental in Pine Plains

Hudson Valley - Picardy Farm: Entire Estate

10 bedrooms
8 bathrooms
Sleeps 20
Match: Sleeps
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Tentrr Signature Site - Hudson Valley Hilltop 1, vacation rental in Pine Plains

Tentrr Signature Site - Hudson Valley Hilltop 1

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Hudson Valley Hilltop 2, vacation rental in Pine Plains

Tentrr Signature Site - Hudson Valley Hilltop 2

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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WELCOME TO THE COUNTRY -  LAKE FRONT PROPERTY - �THE FOX DEN STUDIO, vacation rental in Pine Plains

WELCOME TO THE COUNTRY - LAKE FRONT PROPERTY - �THE FOX DEN STUDIO

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Quiet Country Getaway 4BR/3BA W/ Pool Hot Tub / Movie Theatre, vacation rental in Pine Plains

Quiet Country Getaway 4BR/3BA W/ Pool Hot Tub / Movie Theatre

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lovely Catskill Views, Close to Hudson, 5 minutes from Lake Taghkanic, vacation rental in Pine Plains

Lovely Catskill Views, Close to Hudson, 5 minutes from Lake Taghkanic

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Spring Break Week in Spacious Hudson Valley Home, vacation rental in Pine Plains

Spring Break Week in Spacious Hudson Valley Home

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Private Contemporary Home on Six Acres, vacation rental in Pine Plains

Private Contemporary Home on Six Acres

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern, Light-Filled Cabin in the Woods, Near Catamount Ski, vacation rental in Pine Plains

Modern, Light-Filled Cabin in the Woods, Near Catamount Ski

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Perfection!, vacation rental in Pine Plains

Waterfront Perfection!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Harmony House, Lakeville, Connecticut, vacation rental in Pine Plains

Harmony House, Lakeville, Connecticut

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Breathe the Fresh Clean Air.... 10 Steps to the Lake, vacation rental in Pine Plains

Breathe the Fresh Clean Air.... 10 Steps to the Lake

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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TREEMENDOUS VIEWS COTTAGE, vacation rental in Pine Plains

TREEMENDOUS VIEWS COTTAGE

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Have it all! Lakefront, Pool & Skiing! 5 Bedrooms, vacation rental in Pine Plains

Have it all! Lakefront, Pool & Skiing! 5 Bedrooms

6 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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The Barn - Rustic Chic Loft - Rehabed 1890 Hay Barn - Near Lakes & Hotchkiss, vacation rental in Pine Plains

The Barn - Rustic Chic Loft - Rehabed 1890 Hay Barn - Near Lakes & Hotchkiss

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Contemporary Lakefront, Ski, Tennis and Boat Cozy 3 Bedrooms, vacation rental in Pine Plains

Contemporary Lakefront, Ski, Tennis and Boat Cozy 3 Bedrooms

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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One of a kind ... An Upscale, Picturesque & Private Country Getaway Destination, vacation rental in Pine Plains

One of a kind ... An Upscale, Picturesque & Private Country Getaway Destination

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Outdoor getaway hunting,fishing,skiing..relaxation, vacation rental in Pine Plains

Outdoor getaway hunting,fishing,skiing..relaxation

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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New England Winter Wonderland - 2 Hrs from NYC, vacation rental in Pine Plains

New England Winter Wonderland - 2 Hrs from NYC

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Copake Lake home near cultural attractions Of The Berkshires, vacation rental in Pine Plains

Copake Lake home near cultural attractions Of The Berkshires

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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FARM  HOUSE 3 MILES TO OMEGA RATED #1 BY OMEGA FOLLOWERS 3RD YEAR, vacation rental in Pine Plains

FARM HOUSE 3 MILES TO OMEGA RATED #1 BY OMEGA FOLLOWERS 3RD YEAR

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Newly Renovated Lakefront Getaway on Robinson Pond, vacation rental in Pine Plains

Newly Renovated Lakefront Getaway on Robinson Pond

3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Casa Campagna, vacation rental in Pine Plains

Casa Campagna

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lake House, vacation rental in Pine Plains

Lake House

5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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My Country Home, vacation rental in Pine Plains

My Country Home

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Evergreen Pines Country Estate Villa, vacation rental in Pine Plains

Evergreen Pines Country Estate Villa

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Harley's Hideaway, A Relaxing Escape, vacation rental in Pine Plains

Harley's Hideaway, A Relaxing Escape

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Exclusive Rental in Beautiful Amenia!, vacation rental in Pine Plains

Exclusive Rental in Beautiful Amenia!

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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The FarmHouse, vacation rental in Pine Plains

The FarmHouse

2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Tentrr Signature Site - A Riverwalk, vacation rental in Pine Plains

Tentrr Signature Site - A Riverwalk

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Driftways Farm, vacation rental in Pine Plains

Tentrr Signature Site - Driftways Farm

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Creekside Solitude, vacation rental in Pine Plains

Tentrr Signature Site - Creekside Solitude

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Hucklebuck Railway Camp West, vacation rental in Pine Plains

Tentrr Signature Site - Hucklebuck Railway Camp West

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Tentrr Signature Site - Hucklebuck Railway Camp East, vacation rental in Pine Plains

Tentrr Signature Site - Hucklebuck Railway Camp East

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - MALOWINA RAINFOREST RETREAT, vacation rental in Pine Plains

Tentrr Signature Site - MALOWINA RAINFOREST RETREAT

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr Signature Site - Private Peaceful Farm Venture, vacation rental in Pine Plains

Tentrr Signature Site - Private Peaceful Farm Venture

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Tivoli Trails, vacation rental in Pine Plains

Tentrr Signature Site - Tivoli Trails

1 bedroom
1 bathroom
Sleeps 8
Match: Sleeps
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Babbling Brook Retreat, vacation rental in Pine Plains

Babbling Brook Retreat

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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My Country Home Taghkanic NY, vacation rental in Pine Plains

My Country Home Taghkanic NY

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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NEW Quiet Retreat Minutes to Rhinebeck & Red Hook!, vacation rental in Pine Plains

NEW Quiet Retreat Minutes to Rhinebeck & Red Hook!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Working From Home, vacation rental in Pine Plains

Waterfront Working From Home

2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Tentrr Signature Site - Honeybug Hill near Omega, vacation rental in Pine Plains

Tentrr Signature Site - Honeybug Hill near Omega

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tentrr State Park Site - Lake Taghkanic Lakeside Triple - Site A, vacation rental in Pine Plains

Tentrr State Park Site - Lake Taghkanic Lakeside Triple - Site A

3 bedrooms
1 bathroom
Sleeps 18
Match: Sleeps
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Tentrr State Park Site - Lake Taghkanic Lakeside Single - Site B, vacation rental in Pine Plains

Tentrr State Park Site - Lake Taghkanic Lakeside Single - Site B

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr State Park Site - Lake Taghkanic Lakeside Single - Site C, vacation rental in Pine Plains

Tentrr State Park Site - Lake Taghkanic Lakeside Single - Site C

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Tentrr State Park Site - Lake Taghkanic Secluded Lakeside Double - Site D, vacation rental in Pine Plains

Tentrr State Park Site - Lake Taghkanic Secluded Lakeside Double - Site D

2 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
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Tentrr State Park Site - Lake Taghkanic State Park Site E, vacation rental in Pine Plains

Tentrr State Park Site - Lake Taghkanic State Park Site E

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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