Pine Plains Holiday Rentals

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Holiday Rentals in Pine Plains

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (89)
"Fantastic place to stay! So homey, comfortable, and peaceful. Steven was a fabulous host, and his property is wonderful - in a beautiful garden. The room is large and beyond well equipped. No reason to pay more to stay downtown Hudson. We’re on a month-long New England road trip, and this has been our favorite stay! "
The price is AU$225
includes taxes & fees
9 Jan - 10 Jan 2025
Micosta Leisure Inn

The Farm at Hyde Park

9.8 out of 10, Exceptional, (64)
"Quiet spot out of the city but not too far from Hudson Valley sites. Large vaulted space, fresh eggs from the hen house next door, sky full of stars at night. Great host!"
The Farm at Hyde Park

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

8.2 out of 10, Very good, (42)
"We had a great time at the cabin! It was the perfect escape from the city. The view was gorgeous, and the cabin had everything we needed. We also tried to use the canoe but the padlock is stuck, it might be rusted/need to be replaced. Otherwise everything was perfect!"
The price is AU$235
includes taxes & fees
29 Dec - 30 Dec
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

A-Frame of Mind

10.0 out of 10, Exceptional, (43)
"Beautiful, relaxing stay at this home in Saugerties. We loved the private location yet very close to Woodstock and Saugerties. Nick’s communication was fantastic, responding quickly to our questions. Safe, easy, flexible check in and check out. Inside was mix of rustic cabin and modern appliances, super clean. 100% recommend to anyone. "
A-Frame of Mind

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (22)
"Property was exactly as described. We had a very comfortable stay. The loft was so cozy! Only 4 minutes from our son's trade school. Owners were VERY accommodating! "
The price is AU$362
includes taxes & fees
3 Jan - 4 Jan 2025
Esopus Creek modern Tiny house Retreat!

The Freeman - Newly Renovated 14K SF Estate on 40 Acres

10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres

Private Estate, Heated Yearround Outdoor Pool

10.0 out of 10, Exceptional, (14)
"Beautiful property, well-appointed, and comfortable for extended family of 12."
Private Estate, Heated Yearround Outdoor Pool

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (12)
"Our group of 7 women had a great time in the house. Beautiful property. Nice view of the Hudson. Lots of amenities. Well stocked kitchen. Cozy and comfortable. We enjoyed the Nespresso machine. Lots of room for us to spread out and to hang out together in the living room and enjoy a meal in the dining room. We would definitely stay again. "
Hamptons on the Hudson in South Saugerties

Campfire Cottage: Fireplace, fire pit & no chores!

10.0 out of 10, Exceptional, (23)
"The location was perfect—quiet, peaceful, and close to everything we wanted to do. The house was just as described: clean, comfortable, and well-equipped. We especially appreciated the cozy living room and the fully stocked kitchen, which made cooking meals a breeze. The beds were incredibly comfortable, and we slept soundly every night. The host was also very responsive and provided us with helpful tips about the area. Check-in and check-out were seamless, and we felt well taken care of...
The price is AU$301
includes taxes & fees
6 Jan - 7 Jan 2025
Campfire Cottage: Fireplace, fire pit & no chores!

Antique Farmhouse Totally Restored

10.0 out of 10, Exceptional, (83)
"I'd describe the house as elegantly eclectic. The owner is clearly a collector of interesting items which they arrange in a way that enhance (rather than potentially clutter) the interior. The kitchen and living spaces are open and easy to mingle around. The four bedrooms and three bathrooms easily and comfortably accommodated two couples and two singles. Our stay could not have been better! "
Antique Farmhouse Totally Restored

Sexiest Lil Cabin in Saugerties, NY

8.6 out of 10, Excellent, (7)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
Sexiest Lil Cabin in Saugerties, NY

Charming Artist's Retreat

9.8 out of 10, Exceptional, (130)
"Escaped Long Island’s noise, traffic and overall stress . Listened to owls, watched birds soaring, kicked up leaves and gazed at the periwinkle colored mountains while perched on a bench. Felt safe enough knowing civilization was near enough, would have liked a landline phone just in case of an emergency "
Charming Artist's Retreat

River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

9.8 out of 10, Exceptional, (12)
"We had a wonderful time in Catskill! The house was lots of fun and had tons of space for everyone. We reached out with some questions before our stay and never received a response, many of the outlets didn’t work and the house could have used an extra cleaning before we arrived but overall we had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

9.6 out of 10, Exceptional, (18)
"This apartment was clean and comfortable, and matched the online description. It was not particularly quiet: there is a bar next door, additional VRBO guests upstairs, and trains passing through the neighborhood throughout the night. But the owners provide white noise machines and earplugs, and the noise didn't disrupt my sleep at all. "
The price is AU$389
includes taxes & fees
9 Jan - 10 Jan 2025
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Kingston Crawfish Cottage Near Catskills!

9.8 out of 10, Exceptional, (10)
"We enjoyed our stay at the crawfish cottage. It was clean and had everything we needed. The host, Diane, was great, friendly and very responsive. "
Kingston Crawfish Cottage Near Catskills!

Idillic summer getaway in Litchfield Hills, CT.

10.0 out of 10, Exceptional, (13)
"The place was as described and very comfortable. We enjoyed our stay!"
Idillic summer getaway in Litchfield Hills, CT.

Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County

10.0 out of 10, Exceptional, (14)
"The house is best for a small family that can be active and not worry about hurting the interior. The property is pretty especially the open fields across the street where an evening walk is lovely. House was well stocked and comfortable ."
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County

Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!

9.8 out of 10, Exceptional, (20)
"Large clean house. Great for families. Toys for inside and out. Huge, well stocked kitchen. Very large dining table. Responsive host. Had a great time. Thank you. "
Oversized Country house, Quiet Retreat & Gathering space ~NEW !!!

Mid-Century DJ’s Dream

10.0 out of 10, Exceptional, (24)
"My daughter needed a place to stay while visiting for the holiday. Kevin was easy to reach and responded quickly. The apartment is very cute and was the perfect size. Everything was clean and had some nice personal touches. Im sure a summertime stay would be lovely, when the garden is in bloom"
The price is AU$258
includes taxes & fees
5 Jan - 6 Jan 2025
Mid-Century DJ’s Dream

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (18)
"Very nice, as expected! "
The price is AU$538
includes taxes & fees
3 Jan - 4 Jan 2025
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
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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Other types of properties in Pine Plains you may be interested in

Best Western Plus Kingston Hotel And Conference Center

2.5 star property
8.0 out of 10, Very good, (1001)
"Staff was professional, accommodating and helpful with restaurant suggestions. "
The price is AU$219
includes taxes & fees
5 Jan - 6 Jan 2025
Best Western Plus Kingston Hotel And Conference Center

AutoCamp Catskills

5.0 star property
9.0 out of 10, Wonderful, (336)
"Overall nice Loved the love music in the evening and staff is friendly and helpful. but a few things to consider for the property management: 1) clubhouse is a little cold. People are wearing their coats in the clubhouse. Maybe consider increasing the heat 2) free breakfast is basically coffee, some granola and milk. It really isn’t a breakfast. For the additionalresort fee being asked, I think adding some sort of free pastry, orange juice etc would give guests much better experience. "
The price is AU$395
includes taxes & fees
5 Jan - 6 Jan 2025
AutoCamp Catskills

Hampton Inn Kingston

2.5 star property
9.0 out of 10, Wonderful, (1005)
"We had a great stay. Room was clean, lots of parking and breakfast had many hot qnd cold options. We did not use the pool but lots of people were swimming and enjoying it. The hotel had lots of extra Christmas touches like letters for santa, elf on the shelf and cookies for santa every night. Very cute for all the kids. Staff was very friendly. Management should be wary of over night guests or staff flipping main area tv to inappropriate channels. There was full on nudity during breakfast....
The price is AU$196
includes taxes & fees
5 Jan - 6 Jan 2025
Hampton Inn Kingston
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.

Frequently asked questions

Are there holiday rentals in Pine Plains?

Yes, there are holiday rentals close to the most popular sights in Pine Plains, 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 26 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, Gallatin Town Hall and Pine Plains Library 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.