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Compare 524 Vacation Homes in Pine Plains with updated reviews, rates, and availability.

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (23)
"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 SAR 582
SAR 848 total
includes taxes & fees
6 Jan - 7 Jan
Esopus Creek modern Tiny house Retreat!

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

Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing

10.0 out of 10, Exceptional, (128)
"This lovely lake house felt more updated and larger than the pictures suggest for our Fall trip! There was plenty of space for our 8-person, multi-generational family gathering, and the layout was very conducive to both together-time and breaks. We enjoyed the large dining room table for a big family dinner cooked in the high-end kitchen, after which we retired to the great room, which was more spacious than expected, with a perfect lake view. The ground floor bedroom was great for some...
Lakefront Luxe: Private Dock, Game Rm, Near Hudson & Ski/Tubing

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.

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

10.0 out of 10, Exceptional, (21)
"This property was excellent for our family of 13 plus two dogs. We loved having a great t.v. room where kids could play and a second living area for the adults. Well equipped with games and puzzles. Great location for bucolic road walks. Summer would be great."
Country Estate Outside Hudson - Heated Extra Large Pool w/ Outdoor Barrel Sauna

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (36)
"Our family recently stayed at this incredible vacation rental to celebrate a grandparent’s birthday, and it was truly the perfect setting for a special gathering. With 6 adults and 6 children under the age of 7, finding a place that could comfortably accommodate all of us was no small task—but this property exceeded every expectation. The location was ideal, with easy accessibility for family members traveling from different parts of the country and a manageable drive from Hartford airport....
Beautiful Berkshire Farm House on 160+ Acres

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
10.0 out of 10, Exceptional, (1)
Charming cottage with lake access, wood burning fire place, and WiFi

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

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

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!

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

9.4 out of 10, Exceptional, (20)
"Very nice, as expected! "
The price is SAR 732
SAR 1,411 total
includes taxes & fees
6 Jan - 7 Jan
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Hudson River Way by Woodstock Way Hotel

5.0 star property
The price is SAR 1,172
SAR 1,365 total
includes taxes & fees
20 Jan - 21 Jan
Hudson River Way by Woodstock Way Hotel

Spacious New Luxurious holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (7)
"We had a wonderful time in this beautiful home with lots of room and amenities!"
The price is SAR 2,009
SAR 2,803 total
includes taxes & fees
7 Jan - 8 Jan
Spacious New Luxurious holiday house in lovely Hudson Valley

Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

10.0 out of 10, Exceptional, (115)
"We had a lovely holiday in this truly beautiful dream home. Everything promised in the VRBO advertisement was a reality - from the fireplace, the 4 bedrooms, the ping pong table, the kitchen and the glorious view. We even had a dusting of snow making the trees glisten. Absolutely lovely. Our host was most attentive as well—checking in with us to be sure we understood the heating units and the fireplace. We really had an ideal stay! "
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (5)
"This property is close to many Berkshires and Hudson Valley attractions. In addition to its great location, it is clean, has new appliances, and is on such a peaceful street! There is a lot of space, but it's still incredibly cozy. The beds were extra comfy, as well! I will stay here again if the opportunity presents itself. Thanks for a great stay and the easy check-in/check-out process! "
Hudson Valley and The Berkshires getaway

Special Second Day November discounts @ the River. Text host for discount

9.8 out of 10, Exceptional, (12)
"Beautiful views of the river and was close to all. Place was a bit dusty and the larger bedroom had a very hard bed. Owner was kind and communicative."
Special Second Day November discounts @ the River. Text host for discount

Majestic Mountain Side Sheffield/Great Barrington/SKI

Majestic Mountain Side Sheffield/Great Barrington/SKI

Enjoy the ambiance of the Spirit Horse Farm just 1 mile from the town of Kent CT

2.0 star property
Enjoy the ambiance of the Spirit Horse Farm just 1 mile from the town of Kent CT

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (13)
"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

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 !!!
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

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (90)
"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 SAR 443
SAR 479 total
includes taxes & fees
1 Feb - 2 Feb
Micosta Leisure Inn

'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 SAR 469
SAR 545 total
includes taxes & fees
8 Jan - 9 Jan
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

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
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.