Pine Plains Holiday Rentals

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan
In four months
6 Feb - 8 Feb

Holiday Rentals in Pine Plains

Balcony
Micosta Leisure Inn
Micosta Leisure Inn
3.0 star property
9.2 out of 10, Wonderful, (125)
"Great stay!"
The price is HK$1,011
HK$1,132 total
includes taxes & fees
22 Oct - 23 Oct
Micosta Leisure Inn
Exterior
Sioux Tipi on Chloe's Lake
Sioux Tipi on Chloe's Lake
9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
The price is HK$856
HK$1,133 total
includes taxes & fees
26 Oct - 27 Oct
Sioux Tipi on Chloe's Lake
Terrace/patio
Hamptons on the Hudson in South Saugerties
Hamptons on the Hudson in South Saugerties
10.0 out of 10, Exceptional, (31)
"Lovely property, well-maintained, clean and comfortable, and the host was especially responsive to all communications. Highly recommend."
Hamptons on the Hudson in South Saugerties
Exterior
A Spectacular 50 Mile View of the Hudson Valley in all seasons
A Spectacular 50 Mile View of the Hudson Valley in all seasons
9.8 out of 10, Exceptional, (92)
"Clean and perfect for a couple. Well maintained and provisioned. Yard/view is overgrown and view is obscured mostly by trees since the dwelling is ground level. But overall a pleasant stay in a quiet treed area. Would do again"
A Spectacular 50 Mile View of the Hudson Valley in all seasons
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
8.2 out of 10, Very good, (46)
"A quirky tiny cabin off the beaten path but in need of some upkeep, e.g. toilet not fully attached to the floor in the Tipi room, water has sulphur smell. We were only there for an overnight stay, and I sent a note once we were home, so hopefully the owners get a chance to fix things up! Pricey for its current condition."
The price is HK$972
HK$1,263 total
includes taxes & fees
22 Oct - 23 Oct
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Outdoor dining
Rose Cottage
Rose Cottage
9.2 out of 10, Wonderful, (10)
"It's so peaceful there. It was lovely."
Rose Cottage
Private kitchen
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
2.0 star property
The price is HK$1,099
HK$1,780 total
includes taxes & fees
19 Oct - 20 Oct
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.
Outdoor dining
Sexiest Lil Cabin in Saugerties, NY
Sexiest Lil Cabin in Saugerties, NY
9.0 out of 10, Wonderful, (13)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
The price is HK$875
HK$1,154 total
includes taxes & fees
15 Oct - 16 Oct
Sexiest Lil Cabin in Saugerties, NY
Exterior
The Farm at Hyde Park
The Farm at Hyde Park
9.8 out of 10, Exceptional, (80)
"This was the perfect option for us for a nearby wedding. We ate twice at the River & Post (excellent) and went into Rhinebeck for the Sunday market. The property itself was very accommodating and had everything we needed. The kitchen was well equipped, beds comfortable, and plenty of seating options in the main room. The outside area was also a perfect place for coffee in the morning and we loved the chickens running around. Glenn could not have been nicer. Highly recommend!"
The Farm at Hyde Park
Exterior
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
9.8 out of 10, Exceptional, (32)
"Great location "
The price is HK$1,299
HK$2,714 total
includes taxes & fees
4 Nov - 5 Nov
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Terrace/patio
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
9.6 out of 10, Exceptional, (25)
"Perfect spot to visit grandkids Lots to do"
The price is HK$910
HK$2,143 total
includes taxes & fees
15 Oct - 16 Oct
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Exterior
Summer Lake Cottage, private beach, Berkshire Hills, small village
Summer Lake Cottage, private beach, Berkshire Hills, small village
9.4 out of 10, Exceptional, (83)
"The house has rustic charm and sits right on the lake. It is a beautiful peaceful spot. "
Summer Lake Cottage, private beach, Berkshire Hills, small village
Exterior
Charming 2-bedroom house in fabulous Kingston close to everything
Charming 2-bedroom house in fabulous Kingston close to everything
Charming 2-bedroom house in fabulous Kingston close to everything
Outdoor dining
Esopus Creek modern Tiny house Retreat!
Esopus Creek modern Tiny house Retreat!
9.8 out of 10, Exceptional, (58)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
The price is HK$1,155
HK$1,852 total
includes taxes & fees
22 Oct - 23 Oct
Esopus Creek modern Tiny house Retreat!
Microwave, oven, stovetop, dishwasher
Charming Catskill getaway walking distance to Main St. Pet-friendly!
Charming Catskill getaway walking distance to Main St. Pet-friendly!
10.0 out of 10, Exceptional, (11)
"We had a great stay here! The check in process was super easy and Jiyon was very communicative. The house was super comfortable and conveniently located for a weekend of hiking. Would definitely stay here again!"
Charming Catskill getaway walking distance to Main St. Pet-friendly!
Outdoor pool
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool
10.0 out of 10, Exceptional, (131)
"Stunning views, lovely house and pool, large kitchen, well equipped. Very responsive owner. Strongly recommend for family. "
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool
Property grounds
Private Yacht on Catskill Creek
Private Yacht on Catskill Creek
9.8 out of 10, Exceptional, (27)
"It is a fun alternative to conventional hotel/motel stays. Beautiful waking up on Catskill Creek with as much room as a small hotel room, including 2 double beds plus a dining table that can convert to a bed."
The price is HK$1,155
HK$1,903 total
includes taxes & fees
15 Oct - 16 Oct
Private Yacht on Catskill Creek
Terrace/patio
Spacious New Luxurious holiday house in lovely Hudson Valley
Spacious New Luxurious holiday house in lovely Hudson Valley
9.8 out of 10, Exceptional, (19)
"We loved our stay at this gorgeous home & we will definitely book it again in the future!"
The price is HK$2,976
HK$5,425 total
includes taxes & fees
24 Oct - 25 Oct
Spacious New Luxurious holiday house in lovely Hudson Valley
Fridge, microwave, oven, stovetop
NEW! Gated 21 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
NEW! Gated 21 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
9.6 out of 10, Exceptional, (56)
"We hosted a get-away weekend with friends and the property was perfect. There was lots of privacy, which was nice. The home was well stocked. Communications with the property host and property manager was easy. Everything at the home was in working condition. We had a great time."
NEW! Gated 21 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.
Dining
Guesthouse Cabin vacation rentals in Berkshire County
Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (9)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
The price is HK$3,190
HK$5,561 total
includes taxes & fees
29 Oct - 30 Oct
Guesthouse Cabin vacation rentals in Berkshire County
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

Super 8 by Wyndham Kingston

Super 8 by Wyndham Kingston

10/10 Excellent
"All good "
Raymond 1-night trip
Posted 1 day ago
Super 8 by Wyndham Kingston

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 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?

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

How many holiday rentals will I find in Pine Plains?

With 29 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.