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Compare 641 Vacation Homes in Pine Plains with updated reviews, rates, and availability.

Esopus Creek modern Tiny house Retreat!

9.6 out of 10, Exceptional, (30)
"Had a fantastic stay for a quick overnight trip to ski."
The price is AED 569
AED 897 total
includes taxes & fees
12 May - 13 May
Esopus Creek modern Tiny house Retreat!

Spacious New Luxurious holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (9)
"We had a wonderful time in this beautiful home with lots of room and amenities!"
The price is AED 2,002
AED 3,387 total
includes taxes & fees
12 May - 13 May
Spacious New Luxurious holiday house in lovely Hudson Valley

Hamptons on the Hudson in South Saugerties

9.8 out of 10, Exceptional, (19)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties

Hidden Charm in Hudson Valley In Dutchess County

2.0 star property
10.0 out of 10, Exceptional, (14)
"Kristen's home is a wonderful place! Clean and well kept. Was a nice and quiet spot to call home for a few nights. Wouldn't hesitate to book again. "
Hidden Charm in Hudson Valley In Dutchess County

Mountain View Getaway

10.0 out of 10, Exceptional, (51)
"We loved this property!!"
Mountain View Getaway

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.

Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine

10.0 out of 10, Exceptional, (11)
"Immaculate house beautiful furnishings Very comfortable Everything you need for a relaxing stay Fully equipped"
The price is AED 731
AED 1,613 total
includes taxes & fees
13 May - 14 May
Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine

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

9.6 out of 10, Exceptional, (25)
"Well located and comfortable "
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

9.0 out of 10, Wonderful, (22)
"We had a great time staying at this house. It was quiet and relaxing. We would stay again!"
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

10.0 out of 10, Exceptional, (47)
"We had the most wonderful time! The views are unbelievable - sitting in the pool or hot tub or around the fire pit, watching the barges sail by was so special! We can’t wait to come back!"
Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

Experience Woodstock charm while staying in a cozy cabin in the woods

9.8 out of 10, Exceptional, (26)
"We had a wonderful long weekend experience — beautiful house, perfect heated pool and a very responsive host. "
Experience Woodstock charm while staying in a cozy cabin in the woods

Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

10.0 out of 10, Exceptional, (24)
"Great house that has everything for the family vacation "
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved everything about the house - it was in a great location and perfect for a weekend away with friends!"
The Race Mountain House

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (36)
"The property was centrally located for skiing, and was a comfortable stay."
The price is AED 687
AED 1,621 total
includes taxes & fees
13 May - 14 May
Cheerful 3-bedroom cottage with woodstove

Perfect Nature Haven In Great Barrington

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great time at the house. We had everything we needed. It was close to town. The space is very comfortable."
Perfect Nature Haven In Great Barrington

Lovely 2 queen size bedroom apt one block from Rough Draft and Uptown Kingston

10.0 out of 10, Exceptional, (43)
"It was great!"
Lovely 2 queen size bedroom apt one block from Rough Draft and Uptown Kingston

The Best 3-bedroom house in Tivoli

The Best 3-bedroom house in Tivoli

Cozy Hudson River Waterfront, 3 Bdrm Pool/Quiet Street/Great Views/HITS 2 miles

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great pool on the river! Loved watching th La ge barges go by! "
Cozy Hudson River Waterfront, 3 Bdrm Pool/Quiet Street/Great Views/HITS 2 miles

Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool

9.6 out of 10, Exceptional, (15)
"Enjoyed the holiday with family. "
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool

Exclusive Estate, Heated Yearround Outdoor Pool

9.6 out of 10, Exceptional, (19)
"Beautiful property, well-appointed, and comfortable for extended family of 12."
Exclusive Estate, Heated Yearround Outdoor 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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Other property types in Pine Plains

Postcard Cabins Eastern Catskills

2.0 star property
8.8 out of 10, Excellent, (11)
"We always live these cabins & we've been coming for years!"
The price is AED 551
AED 734 total
includes taxes & fees
11 May - 12 May
Postcard Cabins Eastern Catskills

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (96)
"Third or fourth time staying. Always a pleasure "
The price is AED 477
AED 515 total
includes taxes & fees
22 May - 23 May
Micosta Leisure Inn

Esopus Creek modern Tiny house Retreat!

9.6 out of 10, Exceptional, (30)
"Had a fantastic stay for a quick overnight trip to ski."
The price is AED 569
AED 897 total
includes taxes & fees
12 May - 13 May
Esopus Creek modern Tiny house Retreat!
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.