Pine Plains Holiday Rentals

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Pine Plains holiday rentals

View from property

Cabin in Catskill

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (127 reviews)
"I loved every single part of the stay "
United States
Srijana
The price is HK$855
HK$1,260 total
includes taxes & fees
4 Feb - 5 Feb
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Interior

Cottage in Germantown

Charming loft cottage in tranquil Germantown with WiFi, AC
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.
The price is HK$850
HK$1,686 total
includes taxes & fees
24 Jan - 25 Jan
Charming loft cottage in tranquil Germantown with WiFi, AC
Outdoor dining

Cottage in Catskill

Charming Cottage in the Heart of Catskill & Pet Friendly
10.0 out of 10, Exceptional, (21 reviews)
"Perfect place for a visit to the Hudson Valley. Very comfortable and well taken care of. Friendly neighbors. 3 blocks from Downtown Catskill"
United States
Kirk N.
The price is HK$758
HK$1,905 total
includes taxes & fees
18 Jan - 19 Jan
Charming Cottage in the Heart of Catskill & Pet Friendly
Exterior detail

Holiday Home in Goshen

CT Gate House Goshen CT, Gate House Goshen CT
2.5 star property
9.4 out of 10, Exceptional, (8 reviews)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
The price is HK$828
HK$5,015 total
includes taxes & fees
22 Jan - 23 Jan
CT Gate House Goshen CT, Gate House Goshen CT
Exterior

Aparthotel in Hudson

Micosta Leisure Inn
3.0 star property
9.4 out of 10, Exceptional, (135 reviews)
"Very pleasent stay , and kind helpful staff ."
United States
Kevin
Micosta Leisure Inn
Property grounds

Apartment in Hudson

All comforts of home
9.8 out of 10, Exceptional, (52 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$765
HK$1,031 total
includes taxes & fees
19 Jan - 20 Jan
All comforts of home
Property grounds

Holiday Home in Hudson

All the comforts of home
9.2 out of 10, Wonderful, (29 reviews)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
United States
Marisa P.
The price is HK$828
HK$1,102 total
includes taxes & fees
18 Jan - 19 Jan
All the comforts of home
Terrace/patio

Cottage in Saugerties

Country Cottage with beautiful views and easy access to Catskills activities.
10.0 out of 10, Exceptional, (13 reviews)
"Great spot!"
United States
Dylan
The price is HK$871
HK$1,499 total
includes taxes & fees
19 Jan - 20 Jan
Country Cottage with beautiful views and easy access to Catskills activities.
Property grounds

Apartment in Staatsburg

Mid-Century DJ’s Dream
10.0 out of 10, Exceptional, (44 reviews)
"We had a great overnight stay at DJ’s Dream. Kevin was welcoming and we had the perfect quiet spot to refresh and regroup. Don’t miss the Roosevelt and Vanderbilt attractions in Hyde Park!"
United States
Jean B.
The price is HK$871
HK$1,533 total
includes taxes & fees
20 Jan - 21 Jan
Mid-Century DJ’s Dream
Lobby

Cottage in Catskill

Peaceful warm cozy country cottage nestled beneath the mountains, woodstove
9.8 out of 10, Exceptional, (10 reviews)
"The cottage was comfortable and spotless. My family thoroughly enjoyed their stay at the cottage, and they loved the setting. "
United States
Patricia C.
The price is HK$1,006
HK$2,198 total
includes taxes & fees
8 Feb - 9 Feb
Peaceful warm cozy country cottage nestled beneath the mountains, woodstove
Property grounds

Apartment in Hyde Park

Hudson Valley Farm Getaway- West/Llama Lover Lane
2.0 star property
9.8 out of 10, Exceptional, (6 reviews)
"Perfect little apartment on an amazing farm property...thanks for having us and look forward to returning! "
United States
ADRIENNE
The price is HK$1,244
HK$1,623 total
includes taxes & fees
20 Jan - 21 Jan
Hudson Valley Farm Getaway- West/Llama Lover Lane
Smart TV, fireplace, books

Apartment in Kent

Mid Century Modern Studio w/ Full Kitchen - Newly Built
9.8 out of 10, Exceptional, (10 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is HK$1,521
HK$1,944 total
includes taxes & fees
21 Jan - 22 Jan
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Exterior

Cabin in Catskill

Cozy Catskill Cabin w/ 10-minute Walk to Downtown 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.
The price is HK$1,158
HK$2,557 total
includes taxes & fees
19 Jan - 20 Jan
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Terrace/patio

Apartment in Kingston

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
9.6 out of 10, Exceptional, (27 reviews)
"Very clean very comfortable beds."
United States
Millgate F.
The price is HK$772
HK$1,939 total
includes taxes & fees
20 Jan - 21 Jan
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Desk, iron/ironing board, WiFi, bed sheets

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
9.2 out of 10, Wonderful, (5 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is HK$1,240
HK$1,581 total
includes taxes & fees
27 Jan - 28 Jan
The Brooks Motel: Exceptional Suite
2 bedrooms, desk, free WiFi, bed sheets

Holiday Home in Kingston

Retro Retreat: renovated 2BR, desk, no chore list!
9.6 out of 10, Exceptional, (15 reviews)
"Great, easy, full of everything you’d need. Stayed with 2 others for a work trip and it was perfect! "
United States
Kelley Marie
The price is HK$678
HK$2,306 total
includes taxes & fees
9 Feb - 10 Feb
Retro Retreat: renovated 2BR, desk, no chore list!
Property grounds

Apartment in Dover Plains

Hoppy Hill Farm House
9.6 out of 10, Exceptional, (4 reviews)
"The cabin was perfect. Had everything we needed and clear directions. "
United States
Jocelyn L.
The price is HK$780
HK$1,517 total
includes taxes & fees
20 Jan - 21 Jan
Hoppy Hill Farm House
Fridge, microwave, oven, stovetop

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26 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.
The price is HK$1,137
HK$1,950 total
includes taxes & fees
26 Jan - 27 Jan
Home in Great Barrington
Interior

Holiday Home in Kingston

Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, (31 reviews)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
The price is HK$530
HK$1,905 total
includes taxes & fees
3 Feb - 4 Feb
Campfire Cottage: Fireplace, fire pit & no chores!
Property grounds

Apartment in Rhinebeck Village

Private Studio Close to Downtown Rhinebeck
9.8 out of 10, Exceptional, (27 reviews)
"This a an adorable, well designed, spotless space which was perfect for our over night stay in Rhinebeck. Property a quick walk away from the fairgrounds and downtown was also walkable…the host was absolutely amazing with great communication and detailed instructions! "
United States
Kathy
The price is HK$928
HK$2,179 total
includes taxes & fees
7 Feb - 8 Feb
Private Studio Close to Downtown Rhinebeck
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"everything"
Brian 2-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

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 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.