Pine Plains vacation rentals

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Recommended by KAYAK

Best Pine Plains vacation rentals

Stissing Lake House | Hudson Valley Lake Front - Pine Plains - Building
Stissing Lake House | Hudson Valley Lake Front
Pine Plains, NY
10Wonderful(3)
House
Free Wi-Fi
$2,179+
Check availability
Twin Island Lake House Near Rhinebeck Ny - Pine Plains - Balcony
Twin Island Lake House Near Rhinebeck Ny
Pine Plains, NY
10Wonderful(13)
House
Free Wi-Fi
$512+
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Willow Vale - Stunningly Designed Historical Icon with Hot Tub - Pine Plains - Patio
Willow Vale - Stunningly Designed Historical Icon with Hot Tub
Pine Plains, NY
House
Free Wi-Fi
Pet friendly
$1,049+
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The Cabin-A quiet get away for rest and relaxation - Pine Plains - Dining room
The Cabin-A quiet get away for rest and relaxation
Pine Plains, NY
10Wonderful(1)
House
$673+
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Stylish Pine Plains Home Near Parks and Hiking! - Pine Plains - Living room
Stylish Pine Plains Home Near Parks and Hiking!
Pine Plains, NY
9.7Wonderful(18)
House
Free Wi-Fi
$200+
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Elegant Historic Hudson Valley Gilded Age Mansion On 4+ Parklike Acres - Pine Plains - Dining room
Elegant Historic Hudson Valley Gilded Age Mansion On 4+ Parklike Acres
Pine Plains, NY
9.8Wonderful(81)
House
Free Wi-Fi
$2,342+
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Hudson Valley - Picardy Farm: The Garden House - Pine Plains - Living room
Hudson Valley - Picardy Farm: The Garden House
Pine Plains, NY
House
$549+
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Mid-Century Home Surrounded by Meadows - Pine Plains - Building
Mid-Century Home Surrounded by Meadows
Pine Plains, NY
10Wonderful(5)
House
$766+
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Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats' - Pine Plains - Patio
Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats'
Pine Plains, NY
8.9Very good(19)
Cabin
Free Wi-Fi
$352+
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The Farm House w. Garden Cottage at Picardy Farms - Pine Plains - Kitchen
The Farm House w. Garden Cottage at Picardy Farms
Pine Plains, NY
House
$2,562+
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Hudson Valley - Picardy Farm: The Barn - Pine Plains - Restaurant
Hudson Valley - Picardy Farm: The Barn
Pine Plains, NY
House
$511+
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Peacock Garden Cottage, A Unique Upstate Find - Pine Plains - Living room
Peacock Garden Cottage, A Unique Upstate Find
Pine Plains, NY
9.8Wonderful(12)
House
Free Wi-Fi
$344+
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Hilltop Home on 10 acres w/ hot tub, fire-pit + solar - Pine Plains - Bedroom
Hilltop Home on 10 acres w/ hot tub, fire-pit + solar
Pine Plains, NY
9.8Wonderful(15)
House
Free Wi-Fi
$504+
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Secluded And Spectacular Views - Pine Plains - Building
Secluded And Spectacular Views
Pine Plains, NY
10Wonderful(14)
House
$1,402+
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Family home by Polo fields with great yard & game rm. EV charger, pet friendly! - Pine Plains - Living room
Family home by Polo fields with great yard & game rm. EV charger, pet friendly!
Pine Plains, NY
10Wonderful(3)
House
$593+
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A Country Lodge Straight Out of the Pages of a Great Novel - Pine Plains
A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains, NY
9.8Wonderful(13)
House
$1,298+
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Useful Info

Good to know

Low season

High season

Average price (weekend night)

September
June
$746
Cheapest month to stay with an average 32% drop in price.
Most expensive month to stay with an average 40% rise in price.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Pine Plains vacation rental deals

  • The best vacation rental property in Pine Plains is Elegant Historic Hudson Valley Gilded Age Mansion On 4+ Parklike Acres (9.8, 81 reviews), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Pine Plains, you should consider visiting during the low season. The cheapest vacation homes in Pine Plains can be found in September and October.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Pine Plains for 15 days.

FAQs when booking a vacation home in Pine Plains

  • What types of vacation rentals are available in Pine Plains?

    There are loads of different property types that you can make your vacation home in Pine Plains. You’ll find cabins, farm stays and houses.

  • Are there any pet-friendly vacation rentals in Pine Plains?

    There are a number of dog and pet-friendly Pine Plains vacation rentals, with around 7% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Pine Plains?

    Take a look at our vacation rentals map to find the best vacation rental homes near you.

Where to stay in Pine Plains?

Our map will help you find the perfect place to stay in Pine Plains by showing you the exact location of each vacation rental.

Everything you need to know for your stay in Pine Plains