Pine Plains Holiday Rentals

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Check prices for these dates

Tonight
29 Nov - 30 Nov
Tomorrow
30 Nov - 1 Dec
Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec

Holiday Rentals in Pine Plains

Balcony
Micosta Leisure Inn

Micosta Leisure Inn

3.0 star property
Hudson
9.2 out of 10, Wonderful, (131)
"Clean, pet friendly , just an overall super nice place to stay "
United States
Gail
The price is HK$1,011
HK$1,132 total
includes taxes & fees
30 Nov - 1 Dec
Micosta Leisure Inn
Exterior
The Farm at Hyde Park

The Farm at Hyde Park

Staatsburg
9.8 out of 10, Exceptional, (85)
"Nice stay in an interesting building in an amazing setting. "
United States
Kristen S.
The Farm at Hyde Park
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
8.2 out of 10, Very good, (46)
"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$972
HK$1,263 total
includes taxes & fees
30 Nov - 1 Dec
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Terrace/patio
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

Glasco
10.0 out of 10, Exceptional, (34)
"Beautiful home and fantastic pool. Responsive and friendly host. Our whole family had a great time! "
United States
Courtney W.
Hamptons on the Hudson in South Saugerties
Outdoor dining
Mid-Century DJ’s Dream

Mid-Century DJ’s Dream

Staatsburg
10.0 out of 10, Exceptional, (43)
"Location is well furnished and near many attractionHost versatile and well versed"
United States
Alberto M.
The price is HK$869
HK$1,520 total
includes taxes & fees
30 Nov - 1 Dec
Mid-Century DJ’s Dream
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

Saugerties
9.8 out of 10, Exceptional, (95)
"Enjoyed our stay!"
United States
Mike T.
A Spectacular 50 Mile View of the Hudson Valley in all seasons
Outdoor dining
Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!

Kingston
9.8 out of 10, Exceptional, (60)
"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. "
United States
Rebecca
The price is HK$1,156
HK$1,879 total
includes taxes & fees
2 Dec - 3 Dec
Esopus Creek modern Tiny house Retreat!
Outdoor dining
Sexiest Lil Cabin in Saugerties, NY

Sexiest Lil Cabin in Saugerties, NY

Saugerties
9.0 out of 10, Wonderful, (13)
"A little piece of paradise!"
United States
Christi L.
Sexiest Lil Cabin in Saugerties, NY
Terrace/patio
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi

Kingston
9.6 out of 10, Exceptional, (25)
"A lovely place and Seth is always so helpful."
United States
Lynn L.
The price is HK$666
HK$1,835 total
includes taxes & fees
3 Dec - 4 Dec
Dog-Friendly Hudson Valley Escape with Hot Tub & Jacuzzi
Exterior
Sioux Tipi on Chloe's Lake

Sioux Tipi on Chloe's Lake

Saugerties
9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
United States
Brandon
The price is HK$856
HK$1,133 total
includes taxes & fees
30 Nov - 1 Dec
Sioux Tipi on Chloe's Lake
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, (33)
"Very nice cabin lots of property space "
United States
Martin Z.
The price is HK$1,169
HK$2,556 total
includes taxes & fees
1 Dec - 2 Dec
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Property grounds
Private Yacht on Catskill Creek

Private Yacht on Catskill Creek

Catskill
9.8 out of 10, Exceptional, (28)
"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."
United States
Jay
Private Yacht on Catskill Creek
Interior
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

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

Catskill
9.4 out of 10, Exceptional, (18)
"The house is so historic and very beautiful/interesting. We had a great time. "
United States
Berta T.
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
Smart TV, fireplace, DVD player
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington
10.0 out of 10, Exceptional, (28)
"Wonderful old house, very comfortable space for a large family gathering. The kitchen was well-equipped, and exceptionally clean. The host was communicative and responsive, although everything was so well-thought out on his part, we didn't have much need to talk to the hosts. Excellent location, less than five minutes to Great Barrington, and twenty to Tanglewood and Lenox. "
United States
Johnathan B.
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
1 bedroom, desk, free WiFi
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

Red Hook
9.4 out of 10, Exceptional, (11)
"The loft was easy to find and the perfect location for attending events at Bard and beery picking.Well stocked kitchen and spacious loving room."
United States
Nancy K.
The price is HK$980
HK$1,681 total
includes taxes & fees
1 Dec - 2 Dec
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
Outdoor dining
Charming 2-bedroom Waterfront home with boat access in Saugerties

Charming 2-bedroom Waterfront home with boat access in Saugerties

Saugerties
9.4 out of 10, Exceptional, (8)
"Really enjoyed our stay. The property had all the comforts of home and was beautiful. "
United States
Sean S.
The price is HK$1,323
HK$3,653 total
includes taxes & fees
1 Dec - 2 Dec
Charming 2-bedroom Waterfront home with boat access in Saugerties
Property grounds
Wappinger Cottage - Scandinavian retreat on a creek

Wappinger Cottage - Scandinavian retreat on a creek

Poughkeepsie
10.0 out of 10, Exceptional, (23)
"This was the perfect get away spot! Serene location, lovely amenities, and a gracious host."
United States
Laurie C.
Wappinger Cottage - Scandinavian retreat on a creek
Interior
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Great Barrington
10.0 out of 10, Exceptional, (53)
"Great house for a large group. Lots of seating areas indoors and outdoors to accommodate kids and adults. House was very clean and kitchen was well stocked for cooking. We loved that the bedrooms were nicely separated for privacy, particularly the bunk rooms and nearby game room. Great for the late nighters in the bunch!Beautiful property and less than 10 mins to town."
United States
Carol R.
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
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

Ulster Park
10.0 out of 10, Exceptional, (133)
"Great for a quiet weekend update. New Paltz and Stone Ridge are both close by and have great little main streets. House was very nice and accommodated our group well "
United States
Alex S.
NEW Spectacular Views & Private space on a Scenic Mountain 40ft Salt Water Pool
Terrace/patio
UNIQUE 36 ACR Waterfalls, Steam Shower, BIG Sandbox, Pool Table HOT TUB, POOL

UNIQUE 36 ACR Waterfalls, Steam Shower, BIG Sandbox, Pool Table HOT TUB, POOL

Saugerties
9.6 out of 10, Exceptional, (78)
"Great place to stay while visiting the Catskills area. Beautiful house and property, hot tub and steam shower were both awesome after spending a day out snowboarding. "
United States
Corey S.
UNIQUE 36 ACR Waterfalls, Steam Shower, BIG Sandbox, Pool Table HOT TUB, POOL
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

Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

10/10 Excellent
"Room was good, staff pleasant. The cancelled free breakfasts adding a daily charge but since i booked before then i received free breakfast coupons for each morning. Have to check every BW visit in future though. "
Eugene 2-night trip
Posted 3 days ago
Best Western Plus Kingston Hotel And Conference Center

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
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  • 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?

The Farm at Hyde Park: This holiday home rental outside of Pine Plains is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals will I find in Pine Plains?

With 27 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.