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

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.
$886 nightly
The price is $1,002
Oct 20 - Oct 21
Total with taxes and fees
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.
$1,302 nightly
The price is $1,473
Oct 28 - Oct 29
Total with taxes and fees
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.
$216 nightly
The price is $244
Oct 31 - Nov 1
Total with taxes and fees
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
$192 nightly
The price is $207
Nov 17 - Nov 18
Total with taxes and fees
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.
$255 nightly
The price is $288
Nov 17 - Nov 18
Total with taxes and fees
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
$113 nightly
The price is $127
Oct 20 - Oct 21
Total with taxes and fees
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
$230 nightly
The price is $258
Oct 20 - Oct 21
Total with taxes and fees
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.
$225 nightly
The price is $252
Nov 3 - Nov 4
Total with taxes and fees
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.
$186 nightly
The price is $210
Oct 19 - Oct 20
Total with taxes and fees
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.
$219 nightly
The price is $245
Nov 2 - Nov 3
Total with taxes and fees
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
$269 nightly
The price is $301
Nov 2 - Nov 3
Total with taxes and fees
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.
$239 nightly
The price is $268
Oct 22 - Oct 23
Total with taxes and fees
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.
$994 nightly
The price is $1,124
Oct 19 - Oct 20
Total with taxes and fees
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
$193 nightly
The price is $216
Oct 20 - Oct 21
Total with taxes and fees
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
$606 nightly
The price is $686
Oct 25 - Oct 26
Total with taxes and fees
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
$181 nightly
The price is $203
Oct 20 - Oct 21
Total with taxes and fees
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
$118 nightly
The price is $132
Oct 20 - Oct 21
Total with taxes and fees
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.
$207 nightly
The price is $225
Oct 19 - Oct 20
Total with taxes and fees
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
$210 nightly
The price is $213
Nov 3 - Nov 4
Total with taxes and fees
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 21 hours ago
Pocketbook Hotel and Bath

Find out more about Pine Plains

Everything you need to know about Pine Plains vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pine Plains vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pine Plains vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pine Plains vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pine Plains. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Pine Plains in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $127 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Pine Plains rentals

At Expedia, we put the best Pine Plains vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pine Plains rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pine Plains vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pine Plains. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.