Pine Plains Vacation Rentals

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Browse Select Pine Plains Vacation Homes

The Calf Pen
Property grounds
The Calf Pen
10.0 out of 10, Exceptional, (22)
"We had a great stay! "
The Calf Pen
Cheerful 3-bedroom cottage with woodstove
Property grounds
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (26)
"Impeccably clean, wonderful owner, kitchen with everything, strong WiFi, luxurious master bath. "
The price is CA $318
CA $678 total
includes taxes & fees
Oct 14 - Oct 15
Cheerful 3-bedroom cottage with woodstove
Hudson River Way by Woodstock Way Hotel
Panoramic House | Private kitchen
Hudson River Way by Woodstock Way Hotel
5.0 star property
The price is CA $1,876
CA $2,101 total
includes taxes & fees
Sep 28 - Sep 29
Hudson River Way by Woodstock Way Hotel
Luxury Upstate NY Home on 5 Acres w/ Hot Tub. Great for Families & Groups
Fridge, microwave, oven, stovetop
Luxury Upstate NY Home on 5 Acres w/ Hot Tub. Great for Families & Groups
10.0 out of 10, Exceptional, (87)
"Very nice property. Very nice owner. No problems noted."
Luxury Upstate NY Home on 5 Acres w/ Hot Tub. Great for Families & Groups
Spectacular views and close to Great Barrington.
Smart TV, fireplace
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.
The Farm at Hyde Park
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (61)
"We came up from Brooklyn to see the hot air balloons with my parents and it was just what we needed. Our Host Glen is very gracious and helpful! We loved staying at the Farm. The church and the grounds are beautiful. Glen provided us with fresh eggs, milk and honey. We were also allowed to pick tomatoes from his garden. All very delicious. "
The Farm at Hyde Park
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
9.6 out of 10, Exceptional, (13)
"Me and my husband and my sister and her husband came to the Hudson Valley to place a bench in his hometown in his memory. We thoroughly enjoyed our time at this property. It was just exactly what we needed-quiet and relaxing!"
The price is CA $213
CA $446 total
includes taxes & fees
Sep 29 - Sep 30
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Esopus Creek modern Tiny house Retreat!
Property grounds
Esopus Creek modern Tiny house Retreat!
9.4 out of 10, Exceptional, (11)
"We were in town for a family gathering and this house was in a great location and was exactly as described."
The price is CA $208
CA $303 total
includes taxes & fees
Oct 1 - Oct 2
Esopus Creek modern Tiny house Retreat!
Historic Saugerties Home w/ Deck: River Views!
Fridge, microwave, stovetop, dishwasher
Historic Saugerties Home w/ Deck: River Views!
10.0 out of 10, Exceptional, (13)
"Very peaceful location in our favorite Hudson Valley town, sweet Saugerties! The property manager was extremely responsive, the neighbors were very nice — one even recommended a local swimming hole — and the house was very cute and unique. We loved waking up to the sound of birds and the sunrise over the Hudson. We also loved being able to walk into the village center for dinner and ice cream. The house was clean, comfortable, and we very much enjoyed our stay. "
Historic Saugerties Home w/ Deck: River Views!
Cleo’s Cabin: Private Retreat with Fenced Dog Run
Smart TV, fireplace, books
Cleo’s Cabin: Private Retreat with Fenced Dog Run
8.8 out of 10, Excellent, (8)
"We were in town for HITS and this was a great place to spend a few nights! The cabin had everything we needed and was exactly as pictured online. Beds were super comfortable too. Highly recommend! "
Cleo’s Cabin: Private Retreat with Fenced Dog Run
Lovely 2 queen size bedroom apt one block from Rough Draft and Uptown Kingston
Exterior
Lovely 2 queen size bedroom apt one block from Rough Draft and Uptown Kingston
10.0 out of 10, Exceptional, (34)
"My partner and I so enjoyed our 3 night stay in such a spacious and clean place. They even Provided eggs milk butter champagne and welcome cookies. That was a first!! Walking distance to lots of fine restaurants and sights and a private garden backyard as well. We will definitely return again Alex and Brian. Ithaca "
Lovely 2 queen size bedroom apt one block from Rough Draft and Uptown Kingston
Private + Peaceful 2 BR w/ River Views
Fridge, microwave, oven, stovetop
Private + Peaceful 2 BR w/ River Views
10.0 out of 10, Exceptional, (7)
"I took my husband on a mystery weekend to upstate NY and arranged to have our friends from Ithaca meet us in Clementon. We loved the house. Found it welcoming and easy to manage - beautiful and clean. We went to OPUS 40 and did some other exploring in the area and enjoyed relaxing in the house and reconnecting with our friends. "
Private + Peaceful 2 BR w/ River Views
‘A Gathering Den’ 3-bedroom house. HITS-on-the-Hudson.
Smart TV, books, stereo, printers
‘A Gathering Den’ 3-bedroom house. HITS-on-the-Hudson.
10.0 out of 10, Exceptional, (2)
"This property is perfectly located between Saugerties and Kingston with easy access to both. We wanted a place that was easy to explore the area from and we scored with this house. Everything was clean and we were provided with everything we could need, pots & pans, soap & shampoo, washer & dryer--all of it. We also had plenty of room to do the work we brought with us. The house stayed cool the whole time (day & night) and we really enjoyed it. "
‘A Gathering Den’ 3-bedroom house. HITS-on-the-Hudson.
Spectacular Short Term Vacation Rental in Kent
Exterior
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
Pool
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
9.2 out of 10, Wonderful, (9)
"We had a great stay at this house. The pool was a good size with a deep end. It was really nice to have a pond behind the house. There were several comfortable beds but the trundle was very uncomfortable. The multiple decks were nice. The shampoo and conditioner provided were very nice. Kitchen was lovely and spacious. The house had a little more wear and tear than was evident from the pictures. There was no hammock but there is a picture of one in the listing. The immediate area wasn’t very...
Cortland by AvantStay | Charming Heritage Estate w/ Private Lake & Pool
Kingston Crawfish Cottage Near Catskills!
Fridge, microwave, stovetop, dishwasher
Kingston Crawfish Cottage Near Catskills!
9.8 out of 10, Exceptional, (7)
"AAAAAAAAAAAAA++++++++++!!!!!!!!!!"
Kingston Crawfish Cottage Near Catskills!
4-bedrooms with gym+spa access steps from Garlic Festival
Spa
4-bedrooms with gym+spa access steps from Garlic Festival
9.2 out of 10, Wonderful, (13)
"We enjoyed our stay and Chris was very responsive to any questions. Would definitely stay again."
4-bedrooms with gym+spa access steps from Garlic Festival
The Goshen Glass Chalet
Outdoor dining
The Goshen Glass Chalet
9.4 out of 10, Exceptional, (24)
"Everything was clean, and was a very comfortable home for friends and family."
The Goshen Glass Chalet
Hudson River views with pool and hot tub
Outdoor pool
Hudson River views with pool and hot tub
9.8 out of 10, Exceptional, (19)
"Beautiful location overlooking the Hudson River. Near many cute small towns, nice restaurants and sightseeing opportunities. Weather was dreadfully hot during our stay, so a/c had a hard time keeping the upstairs cool - pool was very welcome respite. Not as clean as we hoped which we communicated to the host after our stay and she waived our cleaning fee."
Hudson River views with pool and hot tub
Saugerties home with gym+spa steps from Garlic Festival
Fridge, microwave, oven, stovetop
Saugerties home with gym+spa steps from Garlic Festival
9.2 out of 10, Wonderful, (12)
"Great location, easy access to HITS. Host was great!"
Saugerties home with gym+spa steps from Garlic Festival
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See all available properties in Pine Plains
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
Balcony
Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (83)
"The owner was fantastic! Super kind and accommodating. Very available for any help or questions. Well maintained, clean and quiet property. Would definitely stay there again! "
The price is CA $152
CA $164 total
includes taxes & fees
Oct 14 - Oct 15
Micosta Leisure Inn
The Farm at Hyde Park
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (61)
"We came up from Brooklyn to see the hot air balloons with my parents and it was just what we needed. Our Host Glen is very gracious and helpful! We loved staying at the Farm. The church and the grounds are beautiful. Glen provided us with fresh eggs, milk and honey. We were also allowed to pick tomatoes from his garden. All very delicious. "
The Farm at Hyde Park
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Property grounds
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
8.4 out of 10, Very good, (41)
"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 CA $168
CA $195 total
includes taxes & fees
Oct 20 - Oct 21
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
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.