Pine Plains Vacation Rentals

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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Pine Plains vacation rentals

View from property

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
Catskill
9.6 out of 10, Exceptional, (151 reviews)
"The cabin was very clean and cozy"
United States
Azma
$150 nightly
The price is $162
Feb 19 - Feb 20
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Exterior

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Saugerties
8.0 out of 10, Very Good, (47 reviews)
"We had an amazing peaceful time at this property. Check in was seamless and we got lots of great recommendations from our hosts that we really enjoyed! It was very private and cozy and really helped us relax and renew! We will definitely be returning. "
United States
Josh M.
$145 nightly
The price is $162
Feb 15 - Feb 16
Total with taxes and fees
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Exterior

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Catskill
9.8 out of 10, Exceptional, (35 reviews)
"Cozy and a great front porch to enjoy morning coffee and the evenings."
United States
Crystal B.
$306 nightly
The price is $330
Feb 16 - Feb 17
Total with taxes and fees
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
$621 nightly
The price is $694
Feb 16 - Feb 17
Total with taxes and fees
Guesthouse Cabin vacation rentals in Berkshire County
Exterior detail

CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT
Goshen
9.4 out of 10, Exceptional, (9 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
$614 nightly
The price is $629
Feb 15 - Feb 16
Total with taxes and fees
CT Gate House Goshen CT, Gate House Goshen CT
Interior

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, (9 reviews)
"Sparkling clean, lovely and cozy hideaway. We only stayed overnight, but the kitchenette would be perfect for a longer stay. Hope we can come back sometime and stay longer."
United States
Peter S.
$190 nightly
The price is $213
Feb 17 - Feb 18
Total with taxes and fees
Charming loft cottage in tranquil Germantown with WiFi, AC
Property grounds

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Palenville
10.0 out of 10, Exceptional, (29 reviews)
"Best place ever!!"
United States
LaurapatOsterwald S.
$343 nightly
The price is $370
Feb 16 - Feb 17
Total with taxes and fees
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Property grounds

All comforts of home

All comforts of home
Hudson
9.8 out of 10, Exceptional, (53 reviews)
"Loved the place and would love to come back. "
United States
Georgine
$118 nightly
The price is $132
Feb 16 - Feb 17
Total with taxes and fees
All comforts of home
Fridge, microwave, oven, stovetop

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (27 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
$236 nightly
The price is $263
Feb 23 - Feb 24
Total with taxes and fees
Home in Great Barrington
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (29 reviews)
"Good for a quick overnight - host was very accommodating when we needed an early check-in."
United States
Katie B.
$126 nightly
The price is $141
Feb 16 - Feb 17
Total with taxes and fees
All the comforts of home
Outdoor dining

Umana's Cabin, cozy, comfy, 5+ acres of land

Umana's Cabin, cozy, comfy, 5+ acres of land
Saugerties
10.0 out of 10, Exceptional, (1 review)
"Secluded and private but just a short drive away from a little town with great bars, restaurants and music venues. "
United States
Paul
$453 nightly
The price is $507
Feb 15 - Feb 16
Total with taxes and fees
Umana's Cabin, cozy, comfy, 5+ acres of land
Terrace/patio

Country Cottage with beautiful views and easy access to Catskills activities.

Country Cottage with beautiful views and easy access to Catskills activities.
Saugerties
10.0 out of 10, Exceptional, (15 reviews)
"Cozy and beautiful house. "
United States
Seung L.
$172 nightly
The price is $192
Feb 16 - Feb 17
Total with taxes and fees
Country Cottage with beautiful views and easy access to Catskills activities.
Lobby

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
10.0 out of 10, Exceptional, (12 reviews)
"Very comfortable home"
United States
Holly
$299 nightly
The price is $323
Feb 17 - Feb 18
Total with taxes and fees
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Interior

Stunning and Cozy loft apartment in kingston .

Stunning and Cozy loft apartment in kingston .
Kingston
9.4 out of 10, Exceptional, (14 reviews)
"Very cute place, clean and comfortable. "
United States
Robin H.
$213 nightly
The price is $239
Feb 17 - Feb 18
Total with taxes and fees
Stunning and Cozy loft apartment in kingston .
Dining

Pet-Friendly Hudson Escape w/ Hot Tub

Pet-Friendly Hudson Escape w/ Hot Tub
Stottville
$286 nightly
The price is $290
Feb 25 - Feb 26
Total with taxes and fees
Pet-Friendly Hudson Escape w/ Hot Tub
Smart TV, fireplace, books

Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
$198 nightly
The price is $224
Mar 2 - Mar 3
Total with taxes and fees
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Interior

Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (31 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
$236 nightly
The price is $264
Feb 23 - Feb 24
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!
Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.4 out of 10, Exceptional, (137 reviews)
"Very pleasent stay , and kind helpful staff ."
United States
Kevin
$136 nightly
The price is $152
Feb 15 - Feb 16
Total with taxes and fees
Micosta Leisure Inn
Outdoor dining

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, (22 reviews)
"Really comfortable and cozy"
Canada
Lynne H.
$311 nightly
The price is $335
Feb 21 - Feb 22
Total with taxes and fees
Charming Cottage in the Heart of Catskill & Pet Friendly
Outdoor dining

Charming 2-bedroom Waterfront home with boat access in Saugerties

Charming 2-bedroom Waterfront home with boat access in Saugerties
Saugerties
9.6 out of 10, Exceptional, (11 reviews)
"Really enjoyed our stay. The property had all the comforts of home and was beautiful. "
United States
Sean S.
$565 nightly
The price is $632
Feb 15 - Feb 16
Total with taxes and fees
Charming 2-bedroom Waterfront home with boat access in Saugerties
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

Hotel Kinsley

Hotel Kinsley

10/10 Excellent
"The staff, Simon, Greg, Ralph and Elizabeth, went above and beyond to make my stay during and harrowing snowstorm feel cozy and welcome. Thank you! "
Karren 2-night trip
Posted 4 days ago
Hotel Kinsley

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 $132 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 close to well known local attractions in Pine Plains, or you can go with a more remote option if you're looking for a relaxing stay.

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

Esopus Creek modern Tiny house Retreat!: You might want to consider this vacation home rental near Pine Plains, which is located on a river and has a fireplace, a barbecue grill, and air-conditioning 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 25 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?

Stissing Lake Park and Thompson Pond 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.