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Pine Plains Holiday Rentals

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5 mi
28 rentals in Pine Plains.
Stylish Pine Plains Home Near Parks & Hiking!, holiday rental in Pine Plains
Stylish Pine Plains Home Near Parks & Hiking!, holiday rental in Pine Plains
Stylish Pine Plains Home Near Parks & Hiking!, holiday rental in Pine Plains

Stylish Pine Plains Home Near Parks & Hiking!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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The Cabin-A quiet get away for rest and relaxation, holiday rental in Pine Plains
The Cabin-A quiet get away for rest and relaxation, holiday rental in Pine Plains
The Cabin-A quiet get away for rest and relaxation, holiday rental in Pine Plains

The Cabin-A quiet get away for rest and relaxation

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Lakefront property at its finest. Nearby fantastic skiing slopes., holiday rental in Pine Plains
Lakefront property at its finest. Nearby fantastic skiing slopes., holiday rental in Pine Plains
Lakefront property at its finest. Nearby fantastic skiing slopes., holiday rental in Pine Plains

Lakefront property at its finest. Nearby fantastic skiing slopes.

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Vintage 50's lake cabin featured in Fresh Cottage Magazine's  'dream retreats', holiday rental in Pine Plains
Vintage 50's lake cabin featured in Fresh Cottage Magazine's  'dream retreats', holiday rental in Pine Plains
Vintage 50's lake cabin featured in Fresh Cottage Magazine's  'dream retreats', holiday rental in Pine Plains

Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats'

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Enchanting cottage in a private oasis, holiday rental in Pine Plains
Enchanting cottage in a private oasis, holiday rental in Pine Plains
Enchanting cottage in a private oasis, holiday rental in Pine Plains

Enchanting cottage in a private oasis

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Peacock Garden Cottage
Now accepting longterm rental 60%discount Nov-April, holiday rental in Pine Plains
Peacock Garden Cottage
Now accepting longterm rental 60%discount Nov-April, holiday rental in Pine Plains
Peacock Garden Cottage
Now accepting longterm rental 60%discount Nov-April, holiday rental in Pine Plains

Peacock Garden Cottage Now accepting longterm rental 60%discount Nov-April

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Hudson Valley - Picardy Farm: The Garden House, holiday rental in Pine Plains
Hudson Valley - Picardy Farm: The Garden House, holiday rental in Pine Plains
Hudson Valley - Picardy Farm: The Garden House, holiday rental in Pine Plains

Hudson Valley - Picardy Farm: The Garden House

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Twin Island Lake House • Hot Tub, holiday rental in Pine Plains
Twin Island Lake House • Hot Tub, holiday rental in Pine Plains
Twin Island Lake House • Hot Tub, holiday rental in Pine Plains

Twin Island Lake House • Hot Tub

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Bluehouse - Charming Renovated Cottage, holiday rental in Pine Plains
The Bluehouse - Charming Renovated Cottage, holiday rental in Pine Plains
The Bluehouse - Charming Renovated Cottage, holiday rental in Pine Plains

The Bluehouse - Charming Renovated Cottage

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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This cabin is a 4 bedroom(s), 2.5 bathrooms, located in Pine Plains, NY., holiday rental in Pine Plains
This cabin is a 4 bedroom(s), 2.5 bathrooms, located in Pine Plains, NY., holiday rental in Pine Plains
This cabin is a 4 bedroom(s), 2.5 bathrooms, located in Pine Plains, NY., holiday rental in Pine Plains

This cabin is a 4 bedroom(s), 2.5 bathrooms, located in Pine Plains, NY.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Elegant 6,000 Sq' 30 Acre Estate - Spectacular Views!, holiday rental in Pine Plains
Elegant 6,000 Sq' 30 Acre Estate - Spectacular Views!, holiday rental in Pine Plains
Elegant 6,000 Sq' 30 Acre Estate - Spectacular Views!, holiday rental in Pine Plains

Elegant 6,000 Sq' 30 Acre Estate - Spectacular Views!

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Breathtaking Lake and Mountain View 90 Miles From NYC, holiday rental in Pine Plains
Breathtaking Lake and Mountain View 90 Miles From NYC, holiday rental in Pine Plains
Breathtaking Lake and Mountain View 90 Miles From NYC, holiday rental in Pine Plains

Breathtaking Lake and Mountain View 90 Miles From NYC

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Hudson Valley - Picardy Farm: Entire Estate, holiday rental in Pine Plains
Hudson Valley - Picardy Farm: Entire Estate, holiday rental in Pine Plains
Hudson Valley - Picardy Farm: Entire Estate, holiday rental in Pine Plains

Hudson Valley - Picardy Farm: Entire Estate

Holiday Rental House
10 bedrooms
8 bathrooms
Sleeps 20
Match: Sleeps
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SUMMER’25-DELIGHT in this PLAYGROUND IN PARADISE!
4BR, TENNIS, PICKLEBALL, holiday rental in Pine Plains
SUMMER’25-DELIGHT in this PLAYGROUND IN PARADISE!
4BR, TENNIS, PICKLEBALL, holiday rental in Pine Plains
SUMMER’25-DELIGHT in this PLAYGROUND IN PARADISE!
4BR, TENNIS, PICKLEBALL, holiday rental in Pine Plains

SUMMER’25-DELIGHT in this PLAYGROUND IN PARADISE! 4BR, TENNIS, PICKLEBALL

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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A Country Lodge Straight Out of the Pages of a Great Novel, holiday rental in Pine Plains
A Country Lodge Straight Out of the Pages of a Great Novel, holiday rental in Pine Plains
A Country Lodge Straight Out of the Pages of a Great Novel, holiday rental in Pine Plains

A Country Lodge Straight Out of the Pages of a Great Novel

Holiday Rental House
4 bedrooms
0 bathrooms
Sleeps 12
Match: Sleeps
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rural, serene + sophisticated space, holiday rental in Pine Plains
rural, serene + sophisticated space, holiday rental in Pine Plains
rural, serene + sophisticated space, holiday rental in Pine Plains

rural, serene + sophisticated space

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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The Blue House - St. Peter Hill Summit, holiday rental in Pine Plains
The Blue House - St. Peter Hill Summit, holiday rental in Pine Plains
The Blue House - St. Peter Hill Summit, holiday rental in Pine Plains

The Blue House - St. Peter Hill Summit

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Tanner Farmhouse - Rural Cozy Escape, holiday rental in Pine Plains
Tanner Farmhouse - Rural Cozy Escape, holiday rental in Pine Plains
Tanner Farmhouse - Rural Cozy Escape, holiday rental in Pine Plains

Tanner Farmhouse - Rural Cozy Escape

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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the suite * gallatin farmstead - private, bucolic, serene setting, holiday rental in Pine Plains
the suite * gallatin farmstead - private, bucolic, serene setting, holiday rental in Pine Plains
the suite * gallatin farmstead - private, bucolic, serene setting, holiday rental in Pine Plains

the suite * gallatin farmstead - private, bucolic, serene setting

Holiday Rental House
1 bedroom
0 bathrooms
Sleeps 2
Match: Sleeps
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Hudson Valley - Picardy Farm: The Barn, holiday rental in Pine Plains
Hudson Valley - Picardy Farm: The Barn, holiday rental in Pine Plains
Hudson Valley - Picardy Farm: The Barn, holiday rental in Pine Plains

Hudson Valley - Picardy Farm: The Barn

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Historic Cottage w Brand New Hot Tub and Game Room, holiday rental in Pine Plains
Historic Cottage w Brand New Hot Tub and Game Room, holiday rental in Pine Plains
Historic Cottage w Brand New Hot Tub and Game Room, holiday rental in Pine Plains

Historic Cottage w Brand New Hot Tub and Game Room

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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, holiday rental in Pine Plains
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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Secluded and Spectacular Views, holiday rental in Pine Plains
Secluded and Spectacular Views, holiday rental in Pine Plains
Secluded and Spectacular Views, holiday rental in Pine Plains

Secluded and Spectacular Views

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Swim, kayak, hike, fish, ski and enjoy the countryside in this rustic cabin, holiday rental in Pine Plains
Swim, kayak, hike, fish, ski and enjoy the countryside in this rustic cabin, holiday rental in Pine Plains
Swim, kayak, hike, fish, ski and enjoy the countryside in this rustic cabin, holiday rental in Pine Plains

Swim, kayak, hike, fish, ski and enjoy the countryside in this rustic cabin

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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The Library Retreat: 3 Building Estate w/Pool+Pond, holiday rental in Pine Plains
The Library Retreat: 3 Building Estate w/Pool+Pond, holiday rental in Pine Plains
The Library Retreat: 3 Building Estate w/Pool+Pond, holiday rental in Pine Plains

The Library Retreat: 3 Building Estate w/Pool+Pond

Holiday Rental House
7 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Mid-Century Home Surrounded by Meadows, holiday rental in Pine Plains
Mid-Century Home Surrounded by Meadows, holiday rental in Pine Plains
Mid-Century Home Surrounded by Meadows, holiday rental in Pine Plains

Mid-Century Home Surrounded by Meadows

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hudson Valley- Picardy Farm: The Main House, holiday rental in Pine Plains
Hudson Valley- Picardy Farm: The Main House, holiday rental in Pine Plains
Hudson Valley- Picardy Farm: The Main House, holiday rental in Pine Plains

Hudson Valley- Picardy Farm: The Main House

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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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, holiday rental in Pine Plains
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

Holiday Rental House
9 bedrooms
10 bathrooms
Sleeps 22
Match: Sleeps
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Showing results 1-28 of 28
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