Search Vacation Homes in Pine Plains

Compare 485 Vacation Homes in Pine Plains with updated reviews, rates, and availability.

Property grounds
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
10.0 out of 10, Exceptional, (65)
"This is our 4th time staying here! And it won't be the last. Weather perfect for sitting on the deck with coffee and cocktails watching the creek slowly flow by. Beds are super comfortable with the BEST pillows. Everything you need for a relaxing stay. O.J, incredible bread with butter and strawberry preserves to greet you! Only a mile from town. An easy walk. Will see you again soon!"
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
Fridge, microwave, oven, stovetop
Luxury Rhinebeck NY Home on 5 Acres w/ NEW Hot Tub. Great for Families & Groups
10.0 out of 10, Exceptional, (85)
"As we drove up the long driveway to this house we quickly felt it was a home for the next few days we stayed there. The space was inviting, comfortable, clean and the decor was beautiful. Our daughter absolutely loved celebrating her 13th birthday at this beautiful home. It was instant relaxation as the surroundings are beautiful and quiet. Gretchen was a lovely host who was very easy to communicate with and provided such helpful information for us during our stay. A few weeks later and we are...
Luxury Rhinebeck NY Home on 5 Acres w/ NEW Hot Tub. Great for Families & Groups
Outdoor dining
Hot Tub and Fireplace, Private Setting -Woodstock, NY
10.0 out of 10, Exceptional, (64)
"This was our 3rd house we've stayed at the houses are always clean and beautiful. Location is private but close enough to shops and restaurants. The hot tub was perfect and clean! The only thing on this one was across the way they are building a house. They were respectful but you may get some noise which I wish I just was told. But house is a 10!! We will staying at the houses again! 😁"
Hot Tub and Fireplace, Private Setting -Woodstock, NY
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Exterior
5-Star New Barn Home - Music Studio, Views & Hot Tub
10.0 out of 10, Exceptional, (18)
"The house is amazing, it delivers on everything stated in the listing and then some. This was our second time staying at Stephen's place and it just keeps getting better. Can't wait for the next one. If you love to listen and play music, its a must."
5-Star New Barn Home - Music Studio, Views & Hot Tub
Fridge, microwave, stovetop, dishwasher
Litchfield County Getaway
10.0 out of 10, Exceptional, (35)
"Very nicely renovated house. Clean and comfortable. Well equipped kitchen. Large comfy living and dining room. Very responsive hosts. Only suggestion would be to provide a few more hooks in the bathrooms for guests to hang personal things (night clothes, used towels, etc.). I would highly recommended this place."
Litchfield County Getaway
Private kitchen
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
10.0 out of 10, Exceptional, (10)
"We had a lovely weekend at this updated farm house. The house is a great combination of old comfortable farm house and updated and clean kitchens and bathrooms. We loved having Artie, the kitty, as our welcoming party."
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Property grounds
Catskill Vacation Rental: Private Deck & Fire Pit
10.0 out of 10, Exceptional, (2)
"This is a great place. The interior furnishings are welcoming and a cool retro style. The household goods are top notch. Super convenient for groceries, drug stores, restaurants. An easy hop to Albany. The fire pit is a nice place to relax. We'll return!"
Catskill Vacation Rental: Private Deck & Fire Pit
TV, fireplace, foosball, books
Stunning Athens Home: Grill, Fire Pit, Pool Access
10.0 out of 10, Exceptional, (1)
Stunning Athens Home: Grill, Fire Pit, Pool Access
View from property
Hudson Valley and The Berkshires getaway
10.0 out of 10, Exceptional, (1)
"Overnight golf trip with cousins and father. Perfect accommodations not far from the copake country club. Great time"
Hudson Valley and The Berkshires getaway
Property grounds
Campfire Bungalow - Kid Friendly
10.0 out of 10, Exceptional, (4)
"Great"
Campfire Bungalow - Kid Friendly
Outdoor dining
Salt Point Guest House on Working Horse Farm!
10.0 out of 10, Exceptional, (50)
"The property location was so close to everything we had planned for our Hyde Park is it. Rebecca was a marvelous host and the property was everything we expected."
Salt Point Guest House on Working Horse Farm!
Outdoor dining
Mountain View Getaway
10.0 out of 10, Exceptional, (35)
"Couldn’t ask for better hosts! The house is impeccable and the views are amazing!"
Mountain View Getaway
Property grounds
Sleepy Hollow Lake Home w/ Deck, Pool Access!
10.0 out of 10, Exceptional, (2)
"We had a wonderful stay. House is brand new, super clean and bright. We loved the access to bikes, plus tennis, pool, and the lake. Will definitely return!"
Sleepy Hollow Lake Home w/ Deck, Pool Access!
Fridge, microwave, oven, stovetop
Campfire Cottage: Fireplace, fire pit & no chores!
10.0 out of 10, Exceptional, (16)
"Matt is a wonderful host! I was very impressed by the cleanliness of the 1 bedroom cabin and how much thought went into providing guests with everything they need. I stayed for four nights and was very comfortable. The bed was so comfortable I slept great. Kingston is a city so some noise is expected. The neighborhood is very quiet at night and you can hear a little noise occasionally in the distance. Matt provides an adjustable sound machine. I put it on low and slept like a baby. Matt is very...
The price is $94
$219 total
includes taxes & fees
May 22 - May 23
Campfire Cottage: Fireplace, fire pit & no chores!
Exterior
Antique Farmhouse Totally Restored
10.0 out of 10, Exceptional, (79)
"There were 6 adults and 2 infants in our party, we were in town for our 25 year high school reunion. The house was incredible and the host went above and beyond to make sure we were well taken care of. This place is a hidden gem and deserves all of the praise."
Antique Farmhouse Totally Restored
Fridge, microwave, oven, stovetop
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
10.0 out of 10, Exceptional, (126)
"Great time, beautiful property, host very responsive and helpful. Awesome sound system bring your CDs."
Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (47)
"Very unusual, appealing proportions, well stocked, perfect location"
The Farm at Hyde Park
TV
Saugerties Home: 3 Decks & Hudson River View
9.8 out of 10, Exceptional, (9)
"This is a great place to stay. Clean and comfy and in a beautiful area. We didn't find the promised linens for the sofa bed, but maybe we just weren't looking in the right place. Other than that, we were very pleased... do pay attention to the notes about the stairs... there are a fair few of them."
Saugerties Home: 3 Decks & Hudson River View
Lake
Rhinebeck Romantic Retreat! Private Guest House, Sky Lights, Spacious.
9.8 out of 10, Exceptional, (101)
"The place is so clean and comfortable, as well as private and relaxing. The location is wonderful, and Tanya and Brad were great hosts. I will definitely stay there again!"
Rhinebeck Romantic Retreat! Private Guest House, Sky Lights, Spacious.
Beach nearby, sun loungers
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
Don't see what you're looking for?
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.

Other property types in Pine Plains

Property grounds
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
10.0 out of 10, Exceptional, (65)
"This is our 4th time staying here! And it won't be the last. Weather perfect for sitting on the deck with coffee and cocktails watching the creek slowly flow by. Beds are super comfortable with the BEST pillows. Everything you need for a relaxing stay. O.J, incredible bread with butter and strawberry preserves to greet you! Only a mile from town. An easy walk. Will see you again soon!"
Woodstock Design-Waterfront, Deck, Private Dock Kayak, Swim
Exterior
The Farm at Hyde Park
9.8 out of 10, Exceptional, (47)
"Very unusual, appealing proportions, well stocked, perfect location"
The Farm at Hyde Park
Balcony
Micosta Leisure Inn
3.0 star property
9.0 out of 10, Wonderful, (72)
"super nice and clean I think I will return the only thing is that it is under construction."
The price is $125
$141 total
includes taxes & fees
May 19 - May 20
Micosta Leisure Inn
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.

Pine Plains Vacation Homes information

Number of reviews
381
Accommodation
485 Vacation Homes
Lowest Price
$190
Highest Price
$350

Recent reviews of Pine Plains hotels
Expedia verified reviews

Monument Mountain Motel

Monument Mountain Motel

5/5 Excellent
"Very convenient and affordable price!!"
A verified traveler from Freeport stayed at Monument Mountain Motel
Posted 2 days ago
Monument Mountain Motel