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Compare 513 Vacation Homes in Pine Plains with updated reviews, rates, and availability.

NEW! Gated 31 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.

9.6 out of 10, Exceptional, (50)
"Our family enjoyed our time at the property- it was a great place for us all to gather. The property managers were incredibly helpful and responsive to the few things that needed attention during our stay. The pool area is the shining star of this home. You can expect the house/ furnishings to be in mostly good shape and as photographed-. The layout of the bedrooms/ shared bathrooms did surprise us a bit despite careful review of photos and listing video tour. Overall great stay!"
NEW! Gated 31 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.

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.

Spacious New 5-bedroom holiday house in lovely Hudson Valley

9.8 out of 10, Exceptional, (6)
"The home was even more stunning in person and from the moment we pulled onto the block we were welcomed by its beautiful surroundings. The home was very comfortable, plenty of space and each of us were very impressed by the thoughtful layout and features. We were in town for a very special event commemorating our brothers amazing achievements and had everything we needed for a very pleasant and memorable stay. The screened in porch was an added bonus and of course, we all gravitated around the...
Spacious New 5-bedroom holiday house in lovely Hudson Valley

Beautiful Berkshire Farm House on 160+ Acres

10.0 out of 10, Exceptional, (34)
"The house was spacious and comfortable for our large group (13 people). The basketball court in the barn was a lot of fun."
Beautiful Berkshire Farm House on 160+ Acres

Hudson River Waterfront, Leaf Peepers Welcome, 3 Bdrm w Pool/Quiet Street

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

The Farm at Hyde Park

9.8 out of 10, Exceptional, (63)
"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

River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

9.8 out of 10, Exceptional, (12)
"We had a wonderful time in Catskill! The house was lots of fun and had tons of space for everyone. We reached out with some questions before our stay and never received a response, many of the outlets didn’t work and the house could have used an extra cleaning before we arrived but overall we had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

5-Star New Barn Home - Music Studio, Views & Hot Tub

10.0 out of 10, Exceptional, (25)
"Perfect house and perfect location. Look forward to this trip yearly. Stephen makes everything easy and is always available. Great escape and property! "
5-Star New Barn Home - Music Studio, Views & Hot Tub

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!

Winter Ski House with gym +spa access

9.4 out of 10, Exceptional, (16)
"We were happy to see there was a full sized kitchen beautifully renovated with a back door to the nice back yard in addition to the wonderful bedroom accommodations. Lots of nice amenities plus antique furnishings but updated baths, just lovely. My only suggestions is more pillows."
The price is SAR 563
SAR 860 total
includes taxes & fees
1 Dec - 2 Dec
Winter Ski House with gym +spa access

Hilltop A-frame chalet, skyline views, heated pool and hot tub, expansive...

10.0 out of 10, Exceptional, (7)
"Lovely home and well equipped would love to stay again. Great service and communication from stay marquis. Thanks again!"
Hilltop A-frame chalet, skyline views, heated pool and hot tub, expansive...

Esopus Creek modern Tiny house Retreat!

9.6 out of 10, Exceptional, (18)
"Nice little place to crash after a show at Bearsville."
The price is SAR 582
SAR 848 total
includes taxes & fees
26 Nov - 27 Nov
Esopus Creek modern Tiny house Retreat!

Winter Ski House with gym +spa access

9.4 out of 10, Exceptional, (10)
"Super convenient to the show grounds which was the #1 draw for the house. We didn't realize there was no washer dryer - but not the end of the world with laundry service close by. House manager was great - very responsive. "
Winter Ski House with gym +spa access

Hudson River Way by Woodstock Way Hotel

5.0 star property
Hudson River Way by Woodstock Way Hotel

Brand New House w gated backyard that is located right at the Saugerties Village

10.0 out of 10, Exceptional, (29)
"The home was perfect for 4 women! Clean! Great girls trip for antiquing- great weather too! "
Brand New House w gated backyard that is located right at the Saugerties Village

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

10.0 out of 10, Exceptional, (112)
"A very nice place in a very nice part of the state. Perfect for groups and families. "
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.

Hudson Valley and The Berkshires getaway

10.0 out of 10, Exceptional, (3)
"We very much enjoyed our stay at this lovely home. The hosts were wonderful communicators!"
Hudson Valley and The Berkshires getaway

Serene Salisbury Rental Home on 26 Acres w/ Deck!

9.8 out of 10, Exceptional, (7)
"Great weekend getaway with family to celebrate "
Serene Salisbury Rental Home on 26 Acres w/ Deck!

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

FREE EV charger and NEMA plug! Breathtaking scenery.

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house with more features than we expected, clean and accommodating "
FREE EV charger and NEMA plug! Breathtaking scenery.
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, (89)
"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 434
SAR 468 total
includes taxes & fees
26 Nov - 27 Nov
Micosta Leisure Inn

The Farm at Hyde Park

9.8 out of 10, Exceptional, (63)
"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

'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 544 total
includes taxes & fees
27 Nov - 28 Nov
'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.