Pine Plains Holiday Rentals

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Pine Plains holiday rentals

TV, fireplace, books

NEW: Chic Modern Barn Style Home in Fun Area

NEW: Chic Modern Barn Style Home in Fun Area
Pine Plains
The price is HK$1,510
HK$5,250 total
includes taxes & fees
10 Jun - 11 Jun
NEW: Chic Modern Barn Style Home in Fun Area
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$6,972
HK$11,539 total
includes taxes & fees
10 Jun - 11 Jun
A Country Lodge Straight Out of the Pages of a Great Novel
Outdoor dining

Private Yacht on Catskill Creek

Private Yacht on Catskill Creek
Catskill
9.8 out of 10, Exceptional, (28 reviews)
"Host was very responsive and ensured a fun stay for us."
United States
Yannie C.
The price is HK$1,163
HK$2,233 total
includes taxes & fees
21 Jun - 22 Jun
Private Yacht on Catskill Creek
Property grounds

Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Dover Plains
10.0 out of 10, Exceptional, (7 reviews)
"We thoroughly enjoyed our stay at this property, clean and spacious tents, impressive shower facility, and all the fun amenities you never thought you needed like an 18 hole putt putt course!"
United States
JoAnna S.
The price is HK$628
HK$1,047 total
includes taxes & fees
16 Jun - 17 Jun
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
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$2,549 total
includes taxes & fees
15 Jun - 16 Jun
Beautiful Yacht on Catskill Creek
Exterior

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, (243 reviews)
"Really great location and near great area."
United States
Sherwin
The price is HK$1,403
HK$1,854 total
includes taxes & fees
16 Jun - 17 Jun
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.
The price is HK$979
HK$1,272 total
includes taxes & fees
17 Jun - 18 Jun
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Property grounds

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 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
22 Jun - 23 Jun
Hoppy Hill Farm House
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$769
HK$1,036 total
includes taxes & fees
17 Jun - 18 Jun
All comforts of home
Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (153 reviews)
"The room was cozy. In a very quiet part of town. The check in process was easy. I would definitely stay again while in town."
United States
Kathleen
The price is HK$1,046
HK$1,172 total
includes taxes & fees
24 Jun - 25 Jun
Micosta Leisure Inn
Interior

Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!
Kingston
10.0 out of 10, Exceptional, (31 reviews)
"The place was amazing! Very easy check in/out process and the host is very responsive. "
United States
Samuel M.
The price is HK$792
HK$2,238 total
includes taxes & fees
10 Jun - 11 Jun
Campfire Cottage: Fireplace, fire pit & no chores!
Interior

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

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.6 out of 10, Exceptional, (16 reviews)
"Host was super welcoming - the pace was gorgeous and had everything we could possibly need! Fabulous stay overall"
United States
Athena P.
The price is HK$1,050
HK$2,429 total
includes taxes & fees
30 Jun - 1 Jul
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Exterior

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

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Catskill
9.6 out of 10, Exceptional, (39 reviews)
"We Absolutely loved our weekend stay here! Beautiful property and just as described!!! Will definitely be back!!!"
United States
Jessica R.
The price is HK$1,481
HK$3,089 total
includes taxes & fees
21 Jun - 22 Jun
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (32 reviews)
"The location was just what we were looking for, the cabin was cozy and clean, and the host was so helpful and welcoming!"
United States
Olivia C.
The price is HK$832
HK$1,107 total
includes taxes & fees
17 Jun - 18 Jun
All the comforts of home
Property grounds

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Palenville
10.0 out of 10, Exceptional, (31 reviews)
"Lovely place almost magical ....the perfect get away . . So well kept."
United States
Nivia
The price is HK$1,586
HK$2,915 total
includes taxes & fees
10 Jun - 11 Jun
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Interior

Stunning and Cozy loft apartment in kingston .

Stunning and Cozy loft apartment in kingston .
Kingston
9.4 out of 10, Exceptional, (16 reviews)
"Very cute place, clean and comfortable. "
United States
Robin H.
The price is HK$1,175
HK$2,062 total
includes taxes & fees
11 Jun - 12 Jun
Stunning and Cozy loft apartment in kingston .
Interior

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Kingston
9.6 out of 10, Exceptional, (84 reviews)
"A quick stop over to explore Kingston and the surrounding area. We had a very nice time, thank you!"
United States
Lee M.
The price is HK$1,298
HK$2,006 total
includes taxes & fees
7 Jul - 8 Jul
Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!
Fridge, microwave, oven, stovetop

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 HK$674
HK$2,097 total
includes taxes & fees
22 Jun - 23 Jun
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
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, (24 reviews)
"Clean and cozy with great amenities! Would come back!"
United States
Kristen B.
The price is HK$1,410
HK$2,808 total
includes taxes & fees
16 Jun - 17 Jun
Charming Cottage in the Heart of Catskill & Pet Friendly
Smart TV, video games, offices

Peaceful Cabin w/ Fire Pit & Creek Access

Peaceful Cabin w/ Fire Pit & Creek Access
Saugerties
9.8 out of 10, Exceptional, (18 reviews)
"The home was extremely clean and nicely appointed. Beds were very comfortable and kitchen was nicely equipped."
United States
Nancy B.
The price is HK$698
HK$2,175 total
includes taxes & fees
10 Jun - 11 Jun
Peaceful Cabin w/ Fire Pit & Creek Access
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

10/10 Excellent
"The hotel is affordable and for the price it met expectations. The rooms were clean, the staff was always very helpful. The breakfast was good. We gave no complaints at all. I recommend it for budget travelers."
Ileana 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:

  • View our selection of featured holiday rentals in Pine Plains
  • Use the map to find apartments and other holiday homes in the Pine Plains neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pine Plains while they last

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?

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!: This holiday home rental outside of Pine Plains is located on a river, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family.

How many holiday rentals will I find in Pine Plains?

With 25 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?

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 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.