Pine Plains Rentals
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Lakefront property at its finest. Nearby fantastic skiing slopes.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Lakefront property at its finest, recently renovated designer house. Beautiful Twin Island Lake. The peace and tranquill ...
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From $526 per night (USD)Expedia
Lakeside Peninsula Escape
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Wake up to stunning views at this lakefront guest house on a private peninsula in Pine Plains, New York. Enjoy the lake ...
From $526 per night (USD)Expedia
From $651 per night (USD)VRBO
Willow Vale • Stunningly Designed Historical Icon w/ Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our historic & meticulously restored home, Willow Vale, situated on a quiet & idyllic country road and nestle ...
From $651 per night (USD)VRBO
From $298 per night (USD)VRBO
Rustic 2 bedroom Stissing Lake Guest Cabin
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Stissing Lake Guest Cottage, a newly renovated 2-bed, 2-bath retreat in the Hudson Valley. Nestled on an 11-ac ...
From $298 per night (USD)VRBO
From $1791 per night (USD)VRBO
Elegant Historic Hudson Valley Gilded Age Mansion On 4+ Parklike Acres
- Bedrooms:
- 9
- Bathrooms:
- 9
- Sleeps:
- 22
The Pines includes a gourmet eat-in kitchen, butler's pantry, formal dining room, music room, library/game room, mud roo ...
From $1791 per night (USD)VRBO
From $1402 per night (USD)VRBO
Stissing Lake House | Hudson Valley Lake Front
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 15
Picture yourself lying in the hammock or with a glass of wine on the porch. Jump into the lake for a refreshing swim, or ...
From $1402 per night (USD)VRBO
From $311 per night (USD)VRBO
Country Chic Lake House in Pine Plains
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Country Chic home in the beautiful Hudson Valley. 2.5 hour drive from NYC and Long Island. Historical town of Pine Plai ...
From $311 per night (USD)VRBO
From $190 per night (USD)Expedia
Stylish Pine Plains Home Near Parks & Hiking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Small town charm meets modern convenience at this updated home in Pine Plains! With 1 bedroom, 1 bathroom, and a fully e ...
From $190 per night (USD)Expedia
From $905 per night (USD)VRBO
Enchanting cottage in a private oasis
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Newly renovated cottage located at Ingadi Farmhouse, a family owned and run farm situated on 127 acres of land in the Hu ...
From $905 per night (USD)VRBO
From $386 per night (USD)Expedia
Twin Island Lake House • Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hudson Valley’s best kept secret. Built in 2018, perched on 4 acres. 3 bedrooms 2 full baths include master suite with p ...
From $386 per night (USD)Expedia
From $1131 per night (USD)VRBO
Secluded and Spectacular Views
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
The Silo Set on 700 acres of wooded Hudson Valley real estate, The Silo is reached by crossing a bridge over a flowing ...
From $1131 per night (USD)VRBO
From $612 per night (USD)Expedia
Mid-Century Home Surrounded by Meadows
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Hideaway This mid-century modern home reigns over a magical world in the heart of New York State’s historic Hudson ...
From $612 per night (USD)Expedia
From $730 per night (USD)VRBO
This cabin is a 4 bedroom(s), 2.5 bathrooms, located in Pine Plains, NY.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The Upstate A is a 3 bedroom + sleeping loft, 2.5 bathroom A-frame set on a quiet cul-de-sac in the heart of the Hudson ...
From $730 per night (USD)VRBO
From $508 per night (USD)VRBO
The Cabin-A quiet get away for rest and relaxation
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Quiet escape from the world. The Cabin settles into its surroundings with deceptive subtlety, while inside it is surpris ...
From $508 per night (USD)VRBO
From $272 per night (USD)VRBO
Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats'
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Rustic cabin by Twin Island Lake, Pine Plains, NY Sitting on quiet Lake Road and nestled in the woods, my rental built i ...
From $272 per night (USD)VRBO
From $388 per night (USD)Expedia
Historic Cottage w Brand New Hot Tub and Game Room
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Restored 1810 cottage where historic charm meets modern living. Follow and tag us on IG @theupstatecub! Welcom ...
From $388 per night (USD)Expedia
From $493 per night (USD)VRBO
Family home by Polo fields with great yard & game rm. EV charger, pet friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Renovated & charming 3BR, 2BA home with spacious yard situated across from Mashomack Polo fields in the picturesque Huds ...
From $493 per night (USD)VRBO
From $1054 per night (USD)Expedia
A Country Lodge Straight Out of the Pages of a Great Novel
- Bedrooms:
- 0
- Bathrooms:
- 4
- Sleeps:
- 12
The Lodge Imagine a country lodge straight out of the pages of a great novel. Rustic chic combines with modern ameniti ...
From $1054 per night (USD)Expedia
From $232 per night (USD)VRBO
Adorable secret hideaway
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
The Nook (Silo garage apartment) This adorable secret hideaway is a self-contained efficiency apartment set in the mids ...
From $232 per night (USD)VRBO
From $1055 per night (USD)VRBO
Upstate Mountain View Retreat
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 11
Escape to this stunning mountain retreat in Dutchess County. This spacious home comfortably accommodates up to 10 guest ...
From $1055 per night (USD)VRBO