Pine Plains Rentals
From $269 per night (USD)VRBO
Twin Island Lake Private Island
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Escape from it all on your own private island. A once in a lifetime experience to reconnect with nature. 10x12 canvas S ...
From $269 per night (USD)VRBO
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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 $350 per night (USD)VRBO
The Bluehouse - Charming Renovated Cottage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Upstate Bluehouse is a light-filled country home located in the quaint town of Pine Plains in the Hudson Valley. It ...
From $350 per night (USD)VRBO
From $945 per night (USD)VRBO
Elegant Historic Hudson Valley Gilded Age Mansion On 4+ Parklike Acres
- Bedrooms:
- 10
- 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 $945 per night (USD)VRBO
From $1300 per night (USD)VRBO
Breathtaking Lake and Mountain View 90 Miles From NYC
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Our picturesque 100 year old Victorian country home is located in the Hudson Valley all on 11 acres, with a breathtaking ...
From $1300 per night (USD)VRBO
From $255 per night (USD)VRBO
Swim, kayak, hike, fish, ski and enjoy the countryside in this rustic cabin
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Revamped and Ready! Get cozy at Stissing Lake Guest Cabin, just 90 miles from NYC. Nestled in the Hudson Valley, this ru ...
From $255 per night (USD)VRBO
From $475 per night (USD)VRBO
Lakefront Home in Hudson Valley Dutchess County, Pine Plains, New York
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Located on a peninsula in Pine Plains, New York. Enjoy the lakefront view from all angles by relaxing on the deck or lou ...
From $475 per night (USD)VRBO
From $169 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 $169 per night (USD)Expedia
From $227 per night (USD)VRBO
Lakefront Designer House in Pine Plains, NY.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Lakefront property at its finest, recently renovated designer house. Beautiful Twin Island Lake. The peace and tranquill ...
From $227 per night (USD)VRBO
From $601 per night (USD)Expedia
This cabin is a 4 bedroom(s), 2.5 bathrooms, located in Pine Plains, NY.
- Bedrooms:
- 3
- 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 $601 per night (USD)Expedia
From $323 per night (USD)VRBO
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 $323 per night (USD)VRBO
From $575 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 $575 per night (USD)Expedia
From $800 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 $800 per night (USD)VRBO
From $950 per night (USD)Expedia
Secluded and Spectacular Views
- Bedrooms:
- 3
- 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 $950 per night (USD)Expedia
From $379 per night (USD)VRBO
Hudson Valley Farmhouse on an Idyllic Country Lane
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Willow Vale House is a charming and serene Eyebrow Colonial farmhouse, located on an idyllic country lane in beautiful D ...
From $379 per night (USD)VRBO
From $428 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 $428 per night (USD)VRBO
From $227 per night (USD)VRBO
Vintage 50's lake cabin featured in Fresh Cottage Magazine's 'dream retreats'
- Bedrooms:
- 2
- 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 $227 per night (USD)VRBO
From $190 per night (USD)Expedia
Adorable secret hideaway
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 1
The Nook (Silo garage apartment) This adorable secret hideaway is a self-contained efficiency apartment set in the mids ...
From $190 per night (USD)Expedia
From $801 per night (USD)VRBO
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 $801 per night (USD)VRBO
From $310 per night (USD)Expedia
Renovated Historic Cottage | By Summer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to The Upstate Cub by Summer, a beautifully designed historic 1810 cottage outfitted with modern amenit ...
From $310 per night (USD)Expedia
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Family Home with pond, beautiful views and stunning sunsets
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
The perfect vacation home to entertain or just enjoy some quiet family time. Close to beautiful walks and proximity to s ...
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From $261 per night (USD)VRBO
Charming 3BR 2BA Oversized Cape with Mountain Views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our charming Hudson Valley retreat, situated on 5 acres of serene land just a short two-hour drive from NYC. ...
From $261 per night (USD)VRBO
From $1063 per night (USD)VRBO
Elegant 6,000 Sq' 30 Acre Estate - Spectacular Views!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Private 6,000 sq' home & 30 acre compound. Perfect family retreat. Sleeps 12+. Main House - 5 BR, 5 1/2 bath, gourm ...
From $1063 per night (USD)VRBO