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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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.
$554 nightly
The price is $626
Sep 28 - Sep 29
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.
$1,119 nightly
The price is $1,266
Oct 16 - Oct 17
Total with taxes and fees
A Country Lodge Straight Out of the Pages of a Great Novel
A neatly made bed with a white pillow, a red pillow, and a white blanket. There is a small bedside table with a lamp.

3. 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.
$230 nightly
The price is $260
Sep 29 - Sep 30
Total with taxes and fees
Hibiscus Suite - Private Studio Apartment in Rhinebeck Village
A kitchen with white cabinetry, granite countertops, and a window with blinds.

4. Charming loft cottage in tranquil Germantown with WiFi, AC

Charming loft cottage in tranquil Germantown with WiFi, AC
Germantown
10.0 out of 10, Exceptional, (14 reviews)
"great location, clean & good communication with host."
United States
Kanna S.
$219 nightly
The price is $245
Sep 30 - Oct 1
Total with taxes and fees
Charming loft cottage in tranquil Germantown with WiFi, AC
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

5. 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, (311 reviews)
"Excellent place"
United States
Yeudin
$201 nightly
The price is $217
Oct 27 - Oct 28
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
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, (178 reviews)
"Great little place."
United States
Kim
$113 nightly
The price is $127
Oct 1 - Oct 2
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
$233 nightly
The price is $261
Sep 29 - Sep 30
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.
$243 nightly
The price is $272
Sep 28 - Sep 29
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, (9 reviews)
"Nice stay for our quick overnight Comfortable space "
United States
jay c.
$183 nightly
The price is $206
Sep 28 - Sep 29
Total with taxes and fees
Pleasant 1-bedroom apartment in Staatsburg perfect for your getaway,
A room with a ceiling fan, a large wall mural, a blue sofa, a colorful rug, and a desk with a chair.

10. 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.
$210 nightly
The price is $238
Oct 7 - Oct 8
Total with taxes and fees
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
A two-story house with a blue exterior, a driveway, and a tree in front.

11. Country House offers 2 bedrooms and a den, lots of parking.

Country House offers 2 bedrooms and a den, lots of parking.
Saugerties
$305 nightly
The price is $342
Sep 28 - Sep 29
Total with taxes and fees
Country House offers 2 bedrooms and a den, lots of parking.
A living room with a television, a cabinet, a glass coffee table, and a framed picture on the wall.

12. Chic Lakeside Oasis|Near Rhinebeck & Millbrook

Chic Lakeside Oasis|Near Rhinebeck & Millbrook
Stanfordville
$578 nightly
The price is $654
Oct 1 - Oct 2
Total with taxes and fees
Chic Lakeside Oasis|Near Rhinebeck & Millbrook
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
9.6 out of 10, Exceptional, (10 reviews)
"Clean, comfortable, private, and plenty of room. Hosts went above and beyond to make our stay easy and memorable."
United States
Polly J.
$928 nightly
The price is $1,050
Sep 28 - Sep 29
Total with taxes and fees
The George is an elegant restored home in the Hudson Valley
A modern interior with a staircase, wooden flooring, a dining area, and a brick wall.

14. Catskill Cottage Walk to Downtown & River Views

Catskill Cottage Walk to Downtown & River Views
Catskill
10.0 out of 10, Exceptional, (30 reviews)
"Great little place to stay at right in downtown!!"
United States
Bryan S.
$149 nightly
The price is $167
Sep 28 - Sep 29
Total with taxes and fees
Catskill Cottage Walk to Downtown & River Views
A wooden cabin with a porch, a grill, and a flower planter.

15. 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
$320 nightly
The price is $358
Sep 28 - Sep 29
Total with taxes and fees
Ideal location for summer and winter activities with plenty of outdoor space.
A farm sign for Clover Brooke Farm in Hyde Park, NY, with a barn and a building in the background.

16. 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.
$202 nightly
The price is $220
Sep 28 - Sep 29
Total with taxes and fees
Hudson Valley Farm Getaway- West/Llama Lover Lane
A kitchen with a stove, cabinets, and a microwave.

17. 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
$190 nightly
The price is $213
Sep 29 - Sep 30
Total with taxes and fees
Butterfly Bungalow Studio · Saugerties/Woodstock
A restaurant with outdoor seating, a sign for 'The New York Restaurant', and a nearby antique shop.

18. Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly
Catskill
10.0 out of 10, Exceptional, (26 reviews)
"Everything was great! The house is in a great location and is very clean, modern and cozy. I would highly recommend staying here! "
United States
Dave P.
$300 nightly
The price is $336
Sep 28 - Sep 29
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
A modern living room with a sectional sofa, a coffee table, and a bar area with stools.

19. Private, Cozy, Clean apartment in lovely Hyde Park

Private, Cozy, Clean apartment in lovely Hyde Park
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"The host was great, the place was really nice and cozy. I would definitely stay here again!!! "
United States
Janet M.
$171 nightly
The price is $193
Sep 28 - Sep 29
Total with taxes and fees
Private, Cozy, Clean apartment in lovely Hyde Park
A compact kitchen with blue cabinets, a white stove, and yellow chairs.

20. 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.
$214 nightly
The price is $240
Sep 30 - Oct 1
Total with taxes and fees
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
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

Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

8/10 Good
"First the good....the hotel was very clean. That is paramount to me, so I gave a very good rating due to that. There is no elevator so if you cannot do the stairs, you need to ask for a first-floor room. Even though we can easily do the stairs, taking up suitcases can be a challenge. Our room was pretty small, but it had all the amenities (TV, microwave, fridge). Breakfast was better than expected being the area was pretty small. No wheat bread - only white and plain bagels. Eggs and sausage were really good as was the waffle maker. All in all, although the beds were comfortable, I'm glad we were only there one night. Best for a brief layover......"
Rosemary 1-night trip
Posted 1 hour ago
Quality Inn Hyde Park Poughkeepsie North

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?

Catskill Cottage Walk to Downtown & River Views: You might want to consider this vacation rental near Pine Plains, which offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.