A rustic barn surrounded by autumn foliage on a hillside.

Pine Plains Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Pine Plains vacation rentals

A modern living room with a grey sofa, a wooden coffee table, and a staircase leading to an upper floor.

1. Chic Barn Style * Fireplace * Near Stissing House

Chic Barn Style * Fireplace * Near Stissing House
Pine Plains
10.0 out of 10, Exceptional, (3 reviews)
"We loved the property and everything was so welcoming! Having a pool there would be the best addition for this place!"
United States
Estefany G.
The price is ￥38,485
￥120,276 total
includes taxes & fees
Oct 29 - Oct 30
Chic Barn Style * Fireplace * Near Stissing House
A modern kitchen with white cabinets, a large island, and a skylight.

2. A Country Lodge Straight Out of the Pages of a Great Novel

A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains
10.0 out of 10, Exceptional, (15 reviews)
"We loved the house and it really added to our upstate experience!!"
United States
stephen r.
The price is ￥125,856
￥213,832 total
includes taxes & fees
Oct 16 - Oct 17
A Country Lodge Straight Out of the Pages of a Great Novel
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

3. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (321 reviews)
"Nice little cabin, well situated to sightseeing"
United States
Darryl
The price is ￥25,488
￥34,364 total
includes taxes & fees
Nov 9 - Nov 10
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

4. Hibiscus Suite - Private Studio Apartment in Rhinebeck Village

Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
Rhinebeck Village
10.0 out of 10, Exceptional, (33 reviews)
"Beautiful place has a great stay!"
United States
Heather O.
The price is ￥18,095
￥43,573 total
includes taxes & fees
Oct 12 - Oct 13
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A room with a ceiling fan, a large wall mural, a blue sofa, a colorful rug, and a desk with a chair.

5. THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
Red Hook
9.2 out of 10, Wonderful, (15 reviews)
"Very sweet little spot that took care of all our needs. Very grateful to have found it and enjoyed our stay."
United States
Jason D.
The price is ￥22,955
￥38,685 total
includes taxes & fees
Oct 31 - Nov 1
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

6. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (185 reviews)
"Great little place."
United States
Kim
The price is ￥15,807
￥17,702 total
includes taxes & fees
Oct 13 - Oct 14
Micosta Leisure Inn
A tented area with two wooden folding chairs and a table, a patterned rug, and a view of greenery and a white tent in the background.

7. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
The price is ￥34,480
￥42,161 total
includes taxes & fees
Oct 13 - Oct 14
Gatherwild Ranch
A modern kitchen with white cabinets, a central island, and a view to the outside.

8. Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.4 out of 10, Exceptional, (10 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is ￥17,810
￥32,864 total
includes taxes & fees
Nov 2 - Nov 3
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

9. The George is an elegant restored home in the Hudson Valley

The George is an elegant restored home in the Hudson Valley
Stanfordville
9.8 out of 10, Exceptional, (11 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
The price is ￥113,983
￥176,761 total
includes taxes & fees
Oct 13 - Oct 14
The George is an elegant restored home in the Hudson Valley
A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

10. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is ￥71,240
￥109,065 total
includes taxes & fees
Oct 15 - Oct 16
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

11. Hudson Valley Farm Getaway- West/Llama Lover Lane

Hudson Valley Farm Getaway- West/Llama Lover Lane
Hyde Park
9.8 out of 10, Exceptional, (8 reviews)
"Great location not too far from the CIA."
United States
alexandra a.
The price is ￥27,274
￥35,679 total
includes taxes & fees
Oct 12 - Oct 13
Hudson Valley Farm Getaway- West/Llama Lover Lane
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

12. Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (33 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is ￥13,456
￥42,021 total
includes taxes & fees
Nov 3 - Nov 4
Campfire Cottage: Fireplace, fire pit & no chores!
A deck with a red umbrella, wooden chairs, and a table with potted plants.

13. Mid-Century DJ’s Dream

Mid-Century DJ’s Dream
Staatsburg
10.0 out of 10, Exceptional, (60 reviews)
"Quiet clean accommodations in a central location for exploring the Hudson Valley."
United States
Alexandra R.
The price is ￥29,446
￥46,385 total
includes taxes & fees
Nov 3 - Nov 4
Mid-Century DJ’s Dream
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

14. Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Kingston
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
The price is ￥10,923
￥39,185 total
includes taxes & fees
Oct 14 - Oct 15
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A dining area with a chandelier, wooden chairs, a table, and a view through a glass door.

15. Creek Views * Chef’s Kitchen * Walk To Lighthouse

Creek Views * Chef’s Kitchen * Walk To Lighthouse
Saugerties
9.8 out of 10, Exceptional, (7 reviews)
"this house was very comfortable and convenient to Saugerties"
United States
molly f.
The price is ￥20,026
￥94,131 total
includes taxes & fees
Nov 2 - Nov 3
Creek Views * Chef’s Kitchen * Walk To Lighthouse
A spacious loft with a high ceiling, exposed wooden beams, a staircase, a flat-screen TV, and a round wooden coffee table with a plant.

16. Stunning and Cozy loft apartment in kingston .

Stunning and Cozy loft apartment in kingston .
Kingston
9.4 out of 10, Exceptional, (18 reviews)
"Very cute place, clean and comfortable. "
United States
Robin H.
The price is ￥23,747
￥42,377 total
includes taxes & fees
Oct 13 - Oct 14
Stunning and Cozy loft apartment in kingston .
A wooden deck with a staircase leading to a covered porch area.

17. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (38 reviews)
"No frills, very clean and peaceful, beautiful setting"
United States
Lori M.
The price is ￥16,813
￥22,378 total
includes taxes & fees
Oct 12 - Oct 13
All the comforts of home
A wooden cabin with a porch, a grill, and a flower planter.

18. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
The price is ￥33,245
￥62,057 total
includes taxes & fees
Oct 12 - Oct 13
Ideal location for summer and winter activities with plenty of outdoor space.
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

19. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is ￥23,747
￥30,143 total
includes taxes & fees
Oct 12 - Oct 13
The Brooks Motel: Exceptional Suite
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

20. Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!
Kingston
9.6 out of 10, Exceptional, (15 reviews)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
The price is ￥14,881
￥48,759 total
includes taxes & fees
Nov 2 - Nov 3
Retro Retreat: renovated 2BR, desk, no chore list!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pine Plains Hotel Reviews

Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

10/10 Excellent
"Great atay"
Jorge 1-night trip
Posted 1 hour ago
Beekman Arms and Delamater Inn

Find out more about Pine Plains

Search for holiday rentals in Pine Plains on Expedia! You can easily find your home rentals, villas, holiday apartments in Pine Plains using one of the methods below:

  • View our selection of featured holiday rentals in Pine Plains
  • Use the map to find apartments and other holiday homes in the Pine Plains neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pine Plains while they last

Look no further and take a look at our great range of rental properties in Pine Plains!

Frequently asked questions

Are there vacation rentals in Pine Plains?

Yes, there are vacation rentals in Pine Plains close to The Stissing Center, or you can choose a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Pine Plains has to offer?

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!: You might want to consider this vacation rental near Pine Plains, which is located on a river and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals will I find in Pine Plains?

With 23 Expedia vacation rentals, you're sure to find just the right place for your Pine Plains stay.

What can I see and do in Pine Plains?

Thompson Pond and Stissing Lake Park are a couple of scenic spots to enjoy the outdoors, whereas The Stissing Center is one of the cultural attractions. While here, Pine Plains Library and Gallatin Town Hall are other places worth a visit.

What are vacation rentals like in Pine Plains?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Pine Plains. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for small groups.