Pine Plains Holiday Rentals

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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Pine Plains holiday rentals

Fridge, microwave, oven, stovetop

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, (13 reviews)
"Our group of parents and riders had a great stay during the Millbrook Horse Trials in July. Clean facility, ample room, responsive host. Would stay again."
United States
Hessie S.
The price is HK$6,971
HK$11,510 total
includes taxes & fees
26 Apr - 27 Apr
A Country Lodge Straight Out of the Pages of a Great Novel
Property grounds

Beautiful Yacht on Catskill Creek

Beautiful Yacht on Catskill Creek
Catskill
10.0 out of 10, Exceptional, (21 reviews)
"So much fun for me and my boys to stay. AJ and Melissa are great hosts!"
United States
Amy G.
The price is HK$1,234
HK$2,084 total
includes taxes & fees
7 May - 8 May
Beautiful Yacht on Catskill Creek
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, (209 reviews)
"Everything was great we can’t wait to return !"
United States
Diana
The price is HK$1,168
HK$1,599 total
includes taxes & fees
28 Apr - 29 Apr
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (142 reviews)
"Steven is the most helpful and kind host I've ever experienced! The property is lovely, and the rooms are cozy. I would definitely recommend staying here especially as a solo traveler."
United States
Salvio
The price is HK$1,018
HK$1,140 total
includes taxes & fees
26 Apr - 27 Apr
Micosta Leisure Inn
Dining

Pet-Friendly Hudson Escape w/ Hot Tub

Pet-Friendly Hudson Escape w/ Hot Tub
Stottville
The price is HK$1,265
HK$2,347 total
includes taxes & fees
26 Apr - 27 Apr
Pet-Friendly Hudson Escape w/ Hot Tub
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.
The price is HK$979
HK$1,272 total
includes taxes & fees
26 Apr - 27 Apr
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
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, (2 reviews)
"Secluded and private but just a short drive away from a little town with great bars, restaurants and music venues. "
United States
Paul
The price is HK$2,108
HK$3,948 total
includes taxes & fees
26 Apr - 27 Apr
Umana's Cabin, cozy, comfy, 5+ acres of land
Property grounds

All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (55 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$768
HK$1,036 total
includes taxes & fees
3 May - 4 May
All comforts of home
Property grounds

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,856
HK$3,946 total
includes taxes & fees
27 Apr - 28 Apr
Cheerful 3-bedroom cottage with woodstove
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, (23 reviews)
"Clean and cozy with great amenities! Would come back!"
United States
Kristen B.
The price is HK$1,410
HK$2,772 total
includes taxes & fees
26 Apr - 27 Apr
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, (12 reviews)
"Beautiful home, beautiful view, owner was great. Would absolutely book this residence again"
United States
Jeffrey B.
The price is HK$3,196
HK$6,097 total
includes taxes & fees
26 Apr - 27 Apr
Charming 2-bedroom Waterfront home with boat access in Saugerties
Exterior

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
10.0 out of 10, Exceptional, (2 reviews)
"Tanya goes above and beyond for her guests. Thanks so much for the stay!"
United States
Lindsay S.
The price is HK$2,506
HK$3,846 total
includes taxes & fees
27 Apr - 28 Apr
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (10 reviews)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
United States
Tom S.
The price is HK$3,133
HK$5,354 total
includes taxes & fees
26 Apr - 27 Apr
Guesthouse Cabin vacation rentals in Berkshire County
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, (38 reviews)
"The house was beautiful, clean, and filled with helpful amenities! "
United States
John C.
The price is HK$1,191
HK$2,676 total
includes taxes & fees
27 Apr - 28 Apr
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Interior

Brand New House w gated backyard that is located right at the Saugerties Village

Brand New House w gated backyard that is located right at the Saugerties Village
Saugerties
10.0 out of 10, Exceptional, (41 reviews)
"Great new and clean property! Very close to downtown, supermarket, and a short drive to Hunter Mountain & Kaaterskill falls. "
United States
Michael
The price is HK$1,332
HK$3,168 total
includes taxes & fees
26 Apr - 27 Apr
Brand New House w gated backyard that is located right at the Saugerties Village
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.
The price is HK$1,527
HK$1,952 total
includes taxes & fees
26 Apr - 27 Apr
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Interior

Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!
Kingston
9.8 out of 10, Exceptional, (75 reviews)
"Wonderful tiny home. "
United States
Kyle E.
The price is HK$1,191
HK$1,921 total
includes taxes & fees
28 Apr - 29 Apr
Esopus Creek modern Tiny house Retreat!
Property grounds

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.6 out of 10, Exceptional, (5 reviews)
"Location was great. Accommodations were clean and comfortable. Host was accessible and responsive. Will stay here again if in the area again."
United States
Ken K.
The price is HK$862
HK$1,604 total
includes taxes & fees
27 Apr - 28 Apr
Hoppy Hill Farm House
Dining

Whispering Estate Guest House - A Romantic Countryside Getaway

Whispering Estate Guest House - A Romantic Countryside Getaway
Goshen
10.0 out of 10, Exceptional, (5 reviews)
"Beautiful property and great location. A true retreat. "
United States
Andrea B.
The price is HK$4,230
HK$6,905 total
includes taxes & fees
26 Apr - 27 Apr
Whispering Estate Guest House - A Romantic Countryside Getaway
Smart TV, fireplace

Escape to a stunning two-story home nestled on serene Esopus Creek in Saugerties

Escape to a stunning two-story home nestled on serene Esopus Creek in Saugerties
Saugerties
The price is HK$1,939
HK$4,206 total
includes taxes & fees
5 May - 6 May
Escape to a stunning two-story home nestled on serene Esopus Creek 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

Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

8/10 Good
"Yes"
Daniel 2-night trip
Posted 1 hour ago
Quality Inn Hyde Park Poughkeepsie North

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:

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

Frequently asked questions

Are there holiday rentals in Pine Plains?

Yes, there are holiday rentals in Pine Plains close to The Stissing Center, or you can select a more secluded option if you're looking for a relaxing stay.

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

Hamptons on the Hudson in South Saugerties: This holiday home rental outside of Pine Plains is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Pine Plains?

With 24 Expedia holiday rentals, you're guaranteed 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 holiday rentals like in Pine Plains?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pine Plains. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family trip.