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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.

Twin Island Lake House •Hot Tub• near Rhinebeck NY
SUPERHOST
Entire residential home · 6 guests · 4 beds · 2 bathrooms
Twin Island Lake House •Hot Tub• near Rhinebeck NYBuilt in 2018, perched on 4 acres. 3 bedrooms, 2 full baths include master bedroom with ensuite. Open concept floor plan. Enjoy spectacular views over the lake and mountains this fall season. Fall foliage wonders from late September to late October. A perfect getaway to relax and recharge in our new hot tub. Great hiking, fishing, kayaking, canoeing, cycling and bird watching. 16 miles to the Village of Rhinebeck. Explore the local farms, restaurants, shops, distilleries and wineries.
The Upstate A - Modern Luxury in the Hudson Valley
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
The Nook - An Adorable Secret Get Away
Barn · 2 guests · 0 beds · 1 bathroom
The Nook - An Adorable Secret Get AwayThe Nook (Silo barn apartment) This adorable cozy get away, is a self-contained efficiency apartment set in the midst of Hudson Valley majesty. Over the garage of a property called The Silo (see listing for details as well as information about the setting), The Nook can be rented alone for one or two people or can be included with The Silo for large gatherings.

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Popular amenities for Pine Plains holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Pine Plains

SUPERHOST
  1. Island
  2. Pine Plains
Private Island on Twin Island Lake
₹17,475 per night
SUPERHOST
  1. Entire cabin
  2. Ancram
Rustic & Renovated Hudson Valley Cabin
₹36,675 per night
SUPERHOST
  1. Entire cottage
  2. Pine Plains
Pine Plains Cottage
₹9,128 per night
SUPERHOST
  1. Entire residential home
  2. Pine Plains
Updated Antique Farmhouse on Idyllic Country Lane
₹23,036 per night
SUPERHOST
  1. Entire cabin
  2. Pine Plains
Idyllic, Secluded Log Cabin with Fabulous Views.
₹21,750 per night
  1. Entire residential home
  2. Pine Plains
The Hideaway - A Magical World
₹43,126 per night
  1. Entire guest house
  2. Pine Plains
Dutchess County, Pine Plains, N.Y. near Rhinebeck.
₹30,000 per night
  1. Entire cottage
  2. Pine Plains
Modern Farmhouse - upstate btw Rhinebeck & Hudson
₹30,000 per night
  1. Farm stay
  2. Pine Plains
Hudson Valley - Picardy Farm: Garden House -
₹40,320 per night
  1. Entire residential home
  2. Pine Plains
A Country Lodge and Flawless Retreat
₹66,751 per night
  1. Entire guest suite
  2. Pine Plains
Rustic 2 bedroom Stissing Lake Guest Cabin
₹16,018 per night
  1. Entire cabin
  2. Pine Plains
The Cabin an idyllic, secluded getaway
₹33,750 per night