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Cottages, Villas, Apartments in Pine Plains
Holiday Rentals
USA
New York (NY)
Cottages, Villas, Apartments in Pine Plains
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Internet or Wifi (28)
Other outdoor space (24)
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Kid friendly (28)
Pet friendly (13)
Smoking allowed (1)
Wheelchair access (0)
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Holiday Rental House (28)
Condominium/Apartment (0)
Cabin Holiday Rental (0)
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Waterfront (5)
Boat Available (3)
Private Chef (0)
Private Beach (0)
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Distance from
5 mi
Stissing Mountain Fire Tower
Thompson Pond
The Stissing Center
Minerva Projects
Chaseholm Farm Creamery
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28 rentals
in Pine Plains.
Stylish Pine Plains Home Near Parks & Hiking!
2 reviews
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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The Cabin-A quiet get away for rest and relaxation
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
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Lakefront property at its finest. Nearby fantastic skiing slopes.
1 review
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
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Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats'
3 reviews
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Enchanting cottage in a private oasis
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3 bedrooms
1 bathroom
Sleeps 6
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Peacock Garden Cottage Now accepting longterm rental 60%discount Nov-April
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 5
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Hudson Valley - Picardy Farm: The Garden House
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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Twin Island Lake House • Hot Tub
5 reviews
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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The Bluehouse - Charming Renovated Cottage
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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This cabin is a 4 bedroom(s), 2.5 bathrooms, located in Pine Plains, NY.
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Elegant 6,000 Sq' 30 Acre Estate - Spectacular Views!
Holiday Rental House
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6 bedrooms
6 bathrooms
Sleeps 12
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Breathtaking Lake and Mountain View 90 Miles From NYC
Holiday Rental House
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6 bedrooms
5 bathrooms
Sleeps 14
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Hudson Valley - Picardy Farm: Entire Estate
1 review
Holiday Rental House
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10 bedrooms
8 bathrooms
Sleeps 20
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SUMMER’25-DELIGHT in this PLAYGROUND IN PARADISE! 4BR, TENNIS, PICKLEBALL
33 reviews
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 10
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A Country Lodge Straight Out of the Pages of a Great Novel
7 reviews
Holiday Rental House
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4 bedrooms
0 bathrooms
Sleeps 12
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rural, serene + sophisticated space
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 5
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The Blue House - St. Peter Hill Summit
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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Tanner Farmhouse - Rural Cozy Escape
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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the suite * gallatin farmstead - private, bucolic, serene setting
Holiday Rental House
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1 bedroom
0 bathrooms
Sleeps 2
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Hudson Valley - Picardy Farm: The Barn
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
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Historic Cottage w Brand New Hot Tub and Game Room
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Lakefront Home in Hudson Valley Dutchess County, Pine Plains, New York
14 reviews
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Secluded and Spectacular Views
4 reviews
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 12
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Swim, kayak, hike, fish, ski and enjoy the countryside in this rustic cabin
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 5
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The Library Retreat: 3 Building Estate w/Pool+Pond
Holiday Rental House
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7 bedrooms
6 bathrooms
Sleeps 12
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Mid-Century Home Surrounded by Meadows
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Hudson Valley- Picardy Farm: The Main House
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
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Elegant Historic Hudson Valley Gilded Age Mansion On 4+ Parklike Acres
87 reviews
Holiday Rental House
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9 bedrooms
10 bathrooms
Sleeps 22
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Showing results 1-28 of 28
Frequently Asked Questions about Pine Plains
Do any holiday rentals in Pine Plains have a pool?
Yes, here are some popular holiday rentals in Pine Plains that have a pool:
Adorable secret hideaway
Stylish Pine Plains Home Near Parks & Hiking!
The Cabin-A quiet get away for rest and relaxation
See all holiday rentals with a pool in Pine Plains on Tripadvisor
Do any holiday rentals in Pine Plains have internet access?
Yes, here are some popular holiday rentals in Pine Plains that have internet access:
Adorable secret hideaway
Stylish Pine Plains Home Near Parks & Hiking!
The Cabin-A quiet get away for rest and relaxation
See all holiday rentals in Pine Plains on Tripadvisor
What are the best pet friendly rentals in Pine Plains?
The best pet friendly rentals in Pine Plains are:
Adorable secret hideaway
The Cabin-A quiet get away for rest and relaxation
Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats'
See all pet friendly holiday rentals in Pine Plains on Tripadvisor
What are some great rentals in Pine Plains that are kid friendly?
Some of the most popular kid friendly rentals in Pine Plains are:
Adorable secret hideaway
Stylish Pine Plains Home Near Parks & Hiking!
The Cabin-A quiet get away for rest and relaxation
See all kid friendly holiday rentals in Pine Plains on Tripadvisor
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