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Holiday rentals in Pine Plains

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Top-rated holiday rentals in Pine Plains

Guests agree: these stays are highly rated for location, cleanliness, and more.

Pine Plains Cottage
SUPERHOST
Entire cottage · 4 guests · 3 beds · 1 bathroom
Pine Plains CottageLocated just 2 hours north of NYC, our country cottage in bucolic Pine Plains is newly renovated and furnished in a modern yet cozy style, welcoming you to a relaxing retreat! It is located in the heart of Pine Plains, a short walk to the town center. Perfect for 2-4 people. We currently have a 2 night min. stay due to the added preparations and 3 night min. for holiday weekends. Contact us directly for week/month/shorter stays and to inquire if we can accommodate your pet or a shorter stay!
Stunning apt on horse farm w/ hot tub + pool table
SUPERHOST
Barn · 4 guests · 2 beds · 1 bathroom
Stunning apt on horse farm w/ hot tub + pool tableStunning apartment with 30ft cathedral ceiling in a large barn on a beautiful horse farm. Large, contemporary, open-spaced living area with gorgeous wood beams and large windows providing a ton of light. A new, fully equipped kitchen and a bathroom with a jacuzzi tub in addition to a shower. A spiral staircase leads to the open second-floor loft sleeping area with a king-sized canopy bed. An additional bed can be brought in for extra guests. The apartment also features a full-sized pool table.
The Upstate A - Modern Luxury in the Hudson Valley
SUPERHOST
Entire cabin · 7 guests · 4 beds · 2.5 bathrooms
The Upstate A - Modern Luxury in the Hudson ValleyThe 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 Valley. Built in 1968, it was fully renovated in 2020-2021. Staying here you’ll experience a cozy yet modern vibe, immersed in nature but with all the accoutrements of an upscale stay. You'll find great hiking in the summer, skiing in the winter, fresh upstate air year-round and serenity all day and night. See for yourself: check us out on IG @upstate_aframe

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Other great holiday rentals in Pine Plains

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Lakefront designer house in Pine Plains, NY.
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The Cabin an idyllic, secluded getaway
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Idyllic, Secluded Log Cabin with Fabulous Views.
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Rustic & Renovated Hudson Valley Cabin
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Hudson Valley - Picardy Farm: Garden House -
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Dutchess County, Pine Plains, N.Y. near Rhinebeck.
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The Hideaway - A Magical World
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Modern Upstate Farmhouse - available for Christmas
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A Country Lodge and Flawless Retreat
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Private Island on Twin Island Lake
SUPERHOST
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Updated Antique Farmhouse on Idyllic Country Lane
SUPERHOST
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Magical Private Island Retreat in Pine Plains