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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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 AED 1,507
AED 3,679 total
includes taxes & fees
20 Oct - 21 Oct
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 AED 3,269
AED 5,410 total
includes taxes & fees
28 Oct - 29 Oct
A Country Lodge Straight Out of the Pages of a Great Novel
A room with a ceiling fan, a large wall mural, a blue sofa, a colorful rug, and a desk with a chair.

3. 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 AED 533
AED 898 total
includes taxes & fees
31 Oct - 1 Nov
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

4. 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, (323 reviews)
"Nice little cabin, well situated to sightseeing"
United States
Darryl
The price is AED 558
AED 762 total
includes taxes & fees
16 Nov - 17 Nov
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.

5. 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 AED 452
AED 1,060 total
includes taxes & fees
17 Nov - 18 Nov
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
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
9.4 out of 10, Exceptional, (189 reviews)
"Great stay"
United States
George
The price is AED 367
AED 411 total
includes taxes & fees
20 Oct - 21 Oct
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 AED 818
AED 999 total
includes taxes & fees
19 Oct - 20 Oct
Gatherwild Ranch
A modern kitchen with a granite countertop, stainless steel appliances, and a built-in oven.

8. 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 AED 272
AED 926 total
includes taxes & fees
3 Nov - 4 Nov
Campfire Cottage: Fireplace, fire pit & no chores!
A modern kitchen with white cabinets, a central island, and a view to the outside.

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

Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
Staatsburg
9.6 out of 10, Exceptional, (11 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
The price is AED 413
AED 771 total
includes taxes & fees
19 Oct - 20 Oct
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

10. 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 AED 253
AED 913 total
includes taxes & fees
16 Nov - 17 Nov
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
A neatly made bed with white bedding and a few colorful pillows, a wooden headboard, and a wall-mounted light fixture.

11. 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 AED 408
AED 1,222 total
includes taxes & fees
27 Oct - 28 Oct
Retro Retreat: renovated 2BR, desk, no chore list!
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.

12. 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 AED 551
AED 983 total
includes taxes & fees
22 Oct - 23 Oct
Stunning and Cozy loft apartment in kingston .
A large wooden dining table surrounded by chairs, with a stone fireplace and large windows in the background.

13. 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, (12 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 AED 2,645
AED 4,084 total
includes taxes & fees
28 Oct - 29 Oct
The George is an elegant restored home in the Hudson Valley
A dining area with a table set for two, a vase with flowers, and a bottle of wine.

14. Charming Yacht on Catskill Creek

Charming Yacht on Catskill Creek
Catskill
9.2 out of 10, Wonderful, (17 reviews)
"Melissa was very welcoming and attentive during my stay. The boat was lovely and well maintained."
United States
Marcello C.
Charming Yacht on Catskill Creek
A kitchen with a stove, cabinets, and a microwave.

15. Butterfly Bungalow Studio · Saugerties/Woodstock

Butterfly Bungalow Studio · Saugerties/Woodstock
Saugerties
10.0 out of 10, Exceptional, (1 review)
"Both the house and host were great. The house was in great shape, clean, comfy and with anything we might needed. 100% recommend!!"
United States
Matias
The price is AED 165
AED 794 total
includes taxes & fees
20 Oct - 21 Oct
Butterfly Bungalow Studio · Saugerties/Woodstock
A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

16. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
The price is AED 1,653
AED 2,518 total
includes taxes & fees
28 Oct - 29 Oct
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Private kitchen

17. Woods Cabin-Kingston/Woodstock, NY.

Woods Cabin-Kingston/Woodstock, NY.
Kingston
9.2 out of 10, Wonderful, (15 reviews)
"Thank you. What an experience!"
United States
Burc
The price is AED 419
AED 745 total
includes taxes & fees
20 Oct - 21 Oct
Woods Cabin-Kingston/Woodstock, NY.
A wooden deck with a staircase leading to a covered porch area.

18. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (64 reviews)
"The room was sufficient to our needs. Didn’t realize it was a multi-unit property or that it was on the second floor."
United States
Douglas
The price is AED 360
AED 486 total
includes taxes & fees
29 Oct - 30 Oct
All comforts of home
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

19. 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 AED 633
AED 828 total
includes taxes & fees
19 Oct - 20 Oct
Hudson Valley Farm Getaway- West/Llama Lover Lane
A compact living space with a kitchenette, a sofa, a coffee table, and a patterned rug.

20. Charming & Quaint 1 bed in Historic Uptown!

Charming & Quaint 1 bed in Historic Uptown!
Kingston
The price is AED 393
AED 828 total
includes taxes & fees
16 Nov - 17 Nov
Charming & Quaint 1 bed in Historic Uptown!
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

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

8/10 Good
"Spa was lovely."
Leandro 1-night trip
Posted 20 hours ago
Pocketbook Hotel and Bath

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.