Search Vacation Homes in Pine Plains

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
6 Jum. II - 8 Jum. II
In two weeks
13 Jum. II - 15 Jum. II
In one month
27 Jum. II - 29 Jum. II
In two months
25 Raj. - 27 Raj.

Compare 659 Vacation Homes in Pine Plains with updated reviews, rates, and availability.

Esopus Creek modern Tiny house Retreat!
Outdoor dining

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 SAR 581
SAR 916 total
includes taxes & fees
3 Jun - 4 Jun
Esopus Creek modern Tiny house Retreat!
Lakefront Summer Spectacular in New England Just 2 Hours From NYC
Interior

Lakefront Summer Spectacular in New England Just 2 Hours From NYC

9.8 out of 10, Exceptional, (69)
"The host was great and the property had everything we wanted and more. We will be back."
Lakefront Summer Spectacular in New England Just 2 Hours From NYC
Hamptons on the Hudson in South Saugerties
Terrace/patio

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (21)
"Beautiful property- not too far from Hunter Mt or Woodstock. House has a lot to offer for adults and/or families with kids. Would highly recommend!"
Hamptons on the Hudson in South Saugerties
Peaceful Catskills Creek House
Property grounds

Peaceful Catskills Creek House

10.0 out of 10, Exceptional, (1)
The price is SAR 818
SAR 1,536 total
includes taxes & fees
1 Jun - 2 Jun
Peaceful Catskills Creek House
Home w/ Fire Pit, Near Downtown Hudson + Skiing!
Terrace/patio

Home w/ Fire Pit, Near Downtown Hudson + Skiing!

2.0 star property
10.0 out of 10, Exceptional, (4)
"Lovely time; great property with comfortable furniture!!"
Home w/ Fire Pit, Near Downtown Hudson + Skiing!
Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.
Exterior

Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.

10.0 out of 10, Exceptional, (19)
"We stayed here for skiing over a holiday weekend. The place was *very* clean and Tara was very responsive to helping with the only issue we had (which was weather related and not related to the house). The house is well outfitted and they also left a few basics for us in the kitchen which was a nice touch."
Cozy home close to Catamount, State Parks and the Harlem Valley Rail Trail.
<br>Escape to our incredibly private home on 30 acres!
Fridge, microwave, oven, stovetop

<br>Escape to our incredibly private home on 30 acres!

10.0 out of 10, Exceptional, (133)
"A wonderful, private house incredibly well stocked clean and comfortable! Perfect location between Saugerties and Woodstock. "
<br>Escape to our incredibly private home on 30 acres!
Serene Waterfront Getaway – Hot Tub, Sauna, Arcade, Kayaks, Outdoor Ping Pong!
Outdoor spa tub

Serene Waterfront Getaway – Hot Tub, Sauna, Arcade, Kayaks, Outdoor Ping Pong!

2.0 star property
10.0 out of 10, Exceptional, (3)
"Friends got together for the NY Sheep and Wool Festival. Everything was clean and comfortable, and we loved sitting on the dock and going out in the kayaks. "
The price is SAR 1,772
SAR 3,195 total
includes taxes & fees
1 Jun - 2 Jun
Serene Waterfront Getaway – Hot Tub, Sauna, Arcade, Kayaks, Outdoor Ping Pong!
The Race Mountain House
Pool

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
Newly Renovated Village Home circa. 1874 Near HITS & Hunter
Interior

Newly Renovated Village Home circa. 1874 Near HITS & Hunter

10.0 out of 10, Exceptional, (29)
"Were there during a nice, seasonal snow storm. Easy walk to restaurants and shops inSaugerties. Eric & Jordan were great hosts "
Newly Renovated Village Home circa. 1874 Near HITS & Hunter
Charming 3-bedroom house in the Catskills-Sleepy Hollow Lake community
Exterior

Charming 3-bedroom house in the Catskills-Sleepy Hollow Lake community

10.0 out of 10, Exceptional, (3)
"Comfortable, clean , easy. "
Charming 3-bedroom house in the Catskills-Sleepy Hollow Lake community
Mountain View Getaway
Outdoor dining

Mountain View Getaway

10.0 out of 10, Exceptional, (52)
"We had a wonderful wknd and the hosts thought of everything, kids had a great time and look forward to coming back."
Mountain View Getaway
The Best 3-bedroom house in Tivoli
Outdoor pool, a heated pool

The Best 3-bedroom house in Tivoli

The Best 3-bedroom house in Tivoli
CT Gate House Goshen CT, Gate House Goshen CT
Exterior detail

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
The price is SAR 376
SAR 2,173 total
includes taxes & fees
1 Jun - 2 Jun
CT Gate House Goshen CT, Gate House Goshen CT
Peaceful Cabin w/ Fire Pit & Creek Access
Dining

Peaceful Cabin w/ Fire Pit & Creek Access

10.0 out of 10, Exceptional, (3)
"Great little space , clean, comfortable and equipped with everything I needed for a nice weekend! Would stay again if ever I return to the area ."
The price is SAR 473
SAR 1,086 total
includes taxes & fees
2 Jun - 3 Jun
Peaceful Cabin w/ Fire Pit & Creek Access
Bohemian style open LOFT
Private kitchen

Bohemian style open LOFT

9.0 out of 10, Wonderful, (11)
"We had a wonderful stay at Stojan’s property! Great spot for a weekend getaway and Stojan was very helpful and responsive if/when needed. Highly recommend! "
Bohemian style open LOFT
Charming 3 bedroom, 2 bathroom Catskills cottage
Fridge, microwave, oven, stovetop

Charming 3 bedroom, 2 bathroom Catskills cottage

4.0 star property
2.0 out of 10, (1)
"The upstairs had a bunch of pee stains and reeked. We had to buy febreeze and carpet cleaner to try and get rid of the smell. There were a bunch of bugs, the couch was covered in dirt and crumbs. It did not look like it was cleaned before we got there. We had to leave and book a room at a nearby hotel. The property manager did not answer our phone calls and the host did not answer our messages until the following morning when we had already left. "
Charming 3 bedroom, 2 bathroom Catskills cottage
4 Mi to Great Barrington: Berkshires Retreat!
Fridge, microwave, stovetop, dishwasher

4 Mi to Great Barrington: Berkshires Retreat!

4 Mi to Great Barrington: Berkshires Retreat!
NEW Modern waterfront home close to Catskill mountains, fire pit, EV charging
Interior

NEW Modern waterfront home close to Catskill mountains, fire pit, EV charging

9.6 out of 10, Exceptional, (23)
"We booked this property for a family ski trip and had a wonderful stay. The hosts were great, and the home was updated, clean and very comfortable. I would not hesitate to book this property again when staying in the area."
The price is SAR 938
SAR 2,147 total
includes taxes & fees
10 Jun - 11 Jun
NEW Modern waterfront home close to Catskill mountains, fire pit, EV charging
Cozy log cabin in Lake Community.
Terrace/patio

Cozy log cabin in Lake Community.

10.0 out of 10, Exceptional, (19)
"It was quiet, cozy, spacious and clean!! So very inviting and we did not want to leave!!"
Cozy log cabin in Lake Community.
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free