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Vacation rentals in Pine Plains

Vacation 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
    SUPERHOSTEntire cottage · 4 guests · 3 beds · 1 bathroom
    Pine Plains Cottage

    Located 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 have a strict 2 night min. stay on the weekend and 3 night min. for holiday weekends. Contact us directly for week/month/shorter stays and to inquire if we can accommodate your dog or a shorter stay!

    What guests are saying:

    “Nina and Peter were awesome to deal with. Very responsive and quick with any pre trip questions/suggestions. Very clean perfect little cottage in quaint little town. Perfect location to anything you would need...... Restaurants, stores etc all very close. Cottage was spotless and clean upon check in...... Even the pups had a welcome gift of their own. Check in/out was simple. Would highly recommended staying at their courage....... Aside from the weekend I plan on booking for the summer haha. Great place and hosts. Thanks Nina and Peter!!!”

  • The Nook - An Adorable Secret Get Away
    Barn · 2 guests · 0 beds · 1 bathroom
    The Nook - An Adorable Secret Get Away

    The 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.

    What guests are saying:

    “Wow, you will see A Million Dollar Landscape from the windows. It was so very very quiet with just the Gorgeous Japanese Cows Moo-Mooing. And oh my, my Ella, my 80 pound Boxer-Mix got to roam the fields in front, play Frisbee, and slug by the wood burning stove. If you are looking for R&R, beauty, quiet, stars at nite, romance, and no rah-rah, then please do come here. The place feels spacious because of the Catherdral Ceiling. We were the only ones on the property, and you are talking about 700 acres. The property also as adjacent huge house that was empty.”

  • Dutchess County, Pine Plains, N.Y. near Rhinebeck.
    Entire guest house · 8 guests · 5 beds · 3 bathrooms
    Dutchess County, Pine Plains, N.Y. near Rhinebeck.

    Enjoy total privacy in our guest house located on a private peninsula in Pine Plains, New York. Enjoy the lakefront view and relax on the deck or in the house sitting by the fireplace. Across the entrance of the property, there is Stissing Lake where you can relax on our private property or go for a swim. There are many things to do in the area. The beautiful town of Rhinebeck is only 15 miles away where you will find amazing restaurants, specialty shops, antique shops and The Center for Performing Arts and much more. If you enjoy skiing, you can hit the slopes in 40 minutes. Try our local wineries, see a polo match, and there are many festivals throughout the year depending on the season. Kids and adults will love the Dutchess County fair that is in town every August. If your a hiker, there are trails near the guest house. If you have any questions, please feel free to ask me. Rita

    What guests are saying:

    “Fantastic four BR home with three full bathrooms. Laundry, living room, family room with dining table. Outdoor grill and deck with dock. The hosts are incredibly generous and we made great use of the kayaks and neighborhood tips. This house is well situated and within walking distance of great hiking and birdwatching to include the Stissing Mountain Fire Tower Trail and the Thompson Lake Nature Preserve. Close to parks and great outdoor space (in addition to what's on the property). The kitchen is large and well equipped. Incredible hospitality, I'd highly recommend and look forward to coming back again.”

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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

Lakefront Writer's Cottage in Rhinebeck
SUPERHOSTEntire cottage
Lakefront Writer's Cottage in Rhinebeck
Price:£197 / night
Harley's Hideaway - Cozy Furnished Apartment
SUPERHOSTEntire guest suite
Harley's Hideaway - Cozy Furnished Apartment
Price:£111 / night
Tiny House  near Bard College and Rhinebeck.
SUPERHOSTTiny house
Tiny House near Bard College and Rhinebeck.
Price:£71 / night
The Barn - Rustic Chic Loft, Hotchkiss, Lakes, Ski
SUPERHOSTEntire house
The Barn - Rustic Chic Loft, Hotchkiss, Lakes, Ski
Price:£205 / night
A retreat rich with history yet made to relax!
SUPERHOSTEntire guest house
A retreat rich with history yet made to relax!
Price:£143 / night
Goose Landing Cottage by the lake with Hot Tub
SUPERHOSTEntire cottage
Goose Landing Cottage by the lake with Hot Tub
Price:£168 / night
Beautiful Farmhouse Escape with Gorgeous Views
Entire house
Beautiful Farmhouse Escape with Gorgeous Views
Price:£238 / night
Private 1Br Cabin on 130 acres w/ Waterfall, Views
SUPERHOSTEntire cabin
Private 1Br Cabin on 130 acres w/ Waterfall, Views
Price:£124 / night
10 Neighbors
SUPERHOSTEntire house
10 Neighbors
Price:£317 / night
Sunset Cottage: Unplug - Relax - Recharge
SUPERHOSTEntire cottage
Sunset Cottage: Unplug - Relax - Recharge
Price:£71 / night
The Maples
Entire house
The Maples
Price:£99 / night
Explore the Hudson Valley from a Private Upstate Cottage
SUPERHOSTEntire house
Explore the Hudson Valley from a Private Upstate Cottage
Price:£178 / night
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