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Pine Plains Holiday 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, holiday 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, holiday 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, holiday 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, holiday 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, holiday rental in Pine Plains

Tentrr Signature Site - Hudson Valley Hilltop 1

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Twin Island Lake House, holiday rental in Pine Plains

Twin Island Lake House

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Hudson Valley Hilltop 2, holiday 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, holiday 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, holiday 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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Waterfront Perfection!, holiday rental in Pine Plains

Waterfront Perfection!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spring Break Week in Spacious Hudson Valley Home, holiday 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, holiday 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, holiday 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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Harmony House, Lakeville, Connecticut, holiday rental in Pine Plains

Harmony House, Lakeville, Connecticut

6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Have it all! Lakefront, Pool & Skiing! 5 Bedrooms, holiday rental in Pine Plains

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

6 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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TREEMENDOUS VIEWS COTTAGE, holiday rental in Pine Plains

TREEMENDOUS VIEWS COTTAGE

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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The Barn - Rustic Chic Loft - Rehabed 1890 Hay Barn - Near Lakes & Hotchkiss, holiday 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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One of a kind ... An Upscale, Picturesque & Private Country Getaway Destination, holiday 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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Breathe the Fresh Clean Air.... 10 Steps to the Lake, holiday 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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New England Winter Wonderland - 2 Hrs from NYC, holiday 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, holiday 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, holiday 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, holiday 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, holiday rental in Pine Plains

Casa Campagna

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Harley's Hideaway, A Relaxing Escape, holiday rental in Pine Plains

Harley's Hideaway, A Relaxing Escape

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Lake House, holiday rental in Pine Plains

Lake House

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

My Country Home

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Exclusive Rental in Beautiful Amenia!, holiday rental in Pine Plains

Exclusive Rental in Beautiful Amenia!

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

The FarmHouse

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

Tentrr Signature Site - Hucklebuck Railway Camp East - Coleman Outfitted Site

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

Tentrr Signature Site - Tivoli Trails

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

Babbling Brook Retreat

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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My Country Home Taghkanic NY, holiday 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!, holiday 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, holiday 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, holiday 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, holiday 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, holiday 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, holiday 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, holiday 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, holiday 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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NEW! Peaceful Getaway w/ Pool, 14 Mi to Rhinebeck!, holiday rental in Pine Plains

NEW! Peaceful Getaway w/ Pool, 14 Mi to Rhinebeck!

3 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Quiet and peaceful cape cod on rural lake setting!, holiday rental in Pine Plains

Quiet and peaceful cape cod on rural lake setting!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Tentrr Signature Site - Sweet Hill Glamping, holiday rental in Pine Plains

Tentrr Signature Site - Sweet Hill Glamping

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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