Search Vacation Homes in Pine Plains

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Vacation Homes in Pine Plains

Exterior detail
CT Gate House Goshen CT, Gate House Goshen CT

CT Gate House Goshen CT, Gate House Goshen CT

2.5 star property
Goshen
9.8 out of 10, Exceptional, (7)
"The property was great and the house was huge even for all 12 of us "
United States
Ryan L.
$627 nightly
The price is $643
Dec 9 - Dec 10
Total with taxes and fees
CT Gate House Goshen CT, Gate House Goshen CT
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Great Barrington
9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
$189 nightly
The price is $211
Dec 9 - Dec 10
Total with taxes and fees
Home in Great Barrington
Fridge, microwave, oven, stovetop
Retro Retreat: renovated 2BR, desk, no chore list!

Retro Retreat: renovated 2BR, desk, no chore list!

Kingston
9.6 out of 10, Exceptional, (14)
"Great little space. Perfect for two adults. Chill living room and well appointed kitchen. It’s a perfect alternative to a hotel, and reasonably priced for what you get. "
United States
Chris S.
$255 nightly
The price is $286
Dec 9 - Dec 10
Total with taxes and fees
Retro Retreat: renovated 2BR, desk, no chore list!
Fridge, microwave, oven, stovetop
Campfire Cottage: Fireplace, fire pit & no chores!

Campfire Cottage: Fireplace, fire pit & no chores!

Kingston
10.0 out of 10, Exceptional, (29)
"Great multi-week stay! Would certainly stay again. "
United States
Jim R.
$220 nightly
The price is $246
Dec 14 - Dec 15
Total with taxes and fees
Campfire Cottage: Fireplace, fire pit & no chores!
Fridge, microwave, oven, stovetop
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!

Kingston
10.0 out of 10, Exceptional, (4)
"Beautiful house to stay in, convenient to numerous restaurants and hikes. Our host was very communicative and had great recommendations for the area!"
United States
Brendan B.
$194 nightly
The price is $217
Dec 9 - Dec 10
Total with taxes and fees
Retro Retreat: 1br home w/ WFH desk, livingroom, fire pit and no chores!
Property grounds
All the comforts of home

All the comforts of home

Hudson
9.2 out of 10, Wonderful, (28)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
United States
Marisa P.
$126 nightly
The price is $141
Dec 9 - Dec 10
Total with taxes and fees
All the comforts of home
Dining
Peaceful Cabin w/ Fire Pit & Creek Access

Peaceful Cabin w/ Fire Pit & Creek Access

Saugerties
10.0 out of 10, Exceptional, (13)
"Lovely home! Easy check in and in a quiet area. "
United States
Rachel B.
$250 nightly
The price is $271
Dec 17 - Dec 18
Total with taxes and fees
Peaceful Cabin w/ Fire Pit & Creek Access
Property grounds
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Sheffield
10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$404 nightly
The price is $451
Dec 9 - Dec 10
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Fridge, microwave, oven, stovetop
Double the Fun: Two Houses, Shared Yard & Fire Pit

Double the Fun: Two Houses, Shared Yard & Fire Pit

Kingston
10.0 out of 10, Exceptional, (4)
"Both houses were vey clean and well kept. I would recommend this to anyone. I would stay here again."
United States
Kelly B.
$441 nightly
The price is $494
Dec 14 - Dec 15
Total with taxes and fees
Double the Fun: Two Houses, Shared Yard & Fire Pit
Dining
Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine

Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine

Lake Katrine
10.0 out of 10, Exceptional, (16)
"Perfect getaway!"
United States
Lynn A.
$374 nightly
The price is $419
Dec 9 - Dec 10
Total with taxes and fees
Brand New House with Huge patio overlooks Esopus Creek at Lake Katrine
Outdoor dining
Esopus Creek modern Tiny house Retreat!

Esopus Creek modern Tiny house Retreat!

Kingston
9.8 out of 10, Exceptional, (62)
"The property was beautiful. Quiet area but close enough to all the places we wanted to go. Our hosts were very gracious, attentive and friendly. Enjoyed our weekend retreat. "
United States
Rebecca
$216 nightly
The price is $241
Dec 10 - Dec 11
Total with taxes and fees
Esopus Creek modern Tiny house Retreat!
Exterior
Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam

Hillsdale
8.4 out of 10, Very Good, (5)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
United States
Stefanie K.
$461 nightly
The price is $517
Dec 9 - Dec 10
Total with taxes and fees
Perfect House In Hillsdale, Brings Friends & Fam
Outdoor dining
Charming 2-bedroom Waterfront home with boat access in Saugerties

Charming 2-bedroom Waterfront home with boat access in Saugerties

Saugerties
9.4 out of 10, Exceptional, (9)
"Really enjoyed our stay. The property had all the comforts of home and was beautiful. "
United States
Sean S.
$433 nightly
The price is $485
Dec 9 - Dec 10
Total with taxes and fees
Charming 2-bedroom Waterfront home with boat access in Saugerties
Fridge, microwave, oven, stovetop
Catskill Stay w/ Deck & Fire Pit

Catskill Stay w/ Deck & Fire Pit

Catskill
8.0 out of 10, Very Good, (2)
"The house was great for a weekend trip with family. We enjoyed cooking in the kitchen, playing games in the cozy living room, and roasting up some s'mores around the bonfire at night. The location was great, close to a grocery store and some nature trails, which was important for us. We all got great sleep in the comfy bedrooms."
United States
Erin S.
$397 nightly
The price is $443
Dec 11 - Dec 12
Total with taxes and fees
Catskill Stay w/ Deck & Fire Pit
Terrace/patio
Hot Tub - Hammock- Games - Grill - Large Colonial

Hot Tub - Hammock- Games - Grill - Large Colonial

Kingston
9.8 out of 10, Exceptional, (9)
"We had a great stay! Great location and was clean and comfortable for all of our friends."
United States
Amanda R.
$455 nightly
The price is $510
Dec 11 - Dec 12
Total with taxes and fees
Hot Tub - Hammock- Games - Grill - Large Colonial
Fridge, microwave, oven, stovetop
Great Barrington Get Away

Great Barrington Get Away

Great Barrington
9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
$464 nightly
The price is $518
Dec 9 - Dec 10
Total with taxes and fees
Great Barrington Get Away
Exterior
Super Comfortable Water-view Home in Saugerties

Super Comfortable Water-view Home in Saugerties

Saugerties
9.6 out of 10, Exceptional, (5)
"A very clean, spacious, and friendly environment with all the amenities you need. "
United States
joshua m.
$578 nightly
The price is $648
Dec 10 - Dec 11
Total with taxes and fees
Super Comfortable Water-view Home in Saugerties
Fridge, microwave, oven, stovetop
Hudson Hot Tub & Pet Escape

Hudson Hot Tub & Pet Escape

2.0 star property
Stottville
$300 nightly
The price is $304
Dec 9 - Dec 10
Total with taxes and fees
Hudson Hot Tub & Pet Escape
Fridge, microwave, oven, stovetop
Peaceful Riverfront Cottage with Private Hot tub

Peaceful Riverfront Cottage with Private Hot tub

Lake Katrine
10.0 out of 10, Exceptional, (9)
"Really enjoyed our stay. Great new place. The owners thought of everything. Loved the fire pit and the hot tub. Very well done. "
United States
Richard O.
$391 nightly
The price is $438
Dec 9 - Dec 10
Total with taxes and fees
Peaceful Riverfront Cottage with Private Hot tub
Smart TV, offices
Brand New House w gated backyard that is located right at the Saugerties Village

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

Saugerties
10.0 out of 10, Exceptional, (38)
"Clean, comfortable, and quiet! Would definitely stay again!!!"
United States
Tanya L.
$395 nightly
The price is $442
Jan 4 - Jan 5, 2026
Total with taxes and fees
Brand New House w gated backyard that is located right at the Saugerties Village
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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Top Pine Plains Hotel Reviews

Quality Inn Hyde Park Poughkeepsie North

Quality Inn Hyde Park Poughkeepsie North

10/10 Excellent
"The staff was very freindly and helpful. I thought this place was a great value. Clean room. Breakfast was good. I took advantage of the fitness room which was nice to have. Good location, close to restaurants and a grocery store. "
Mark 1-night trip
Posted 2 days ago
Quality Inn Hyde Park Poughkeepsie North

Find out more about Pine Plains

Pine Plains Vacation Homes information

Number of reviews
332
Accommodation
623 Vacation Homes
Lowest Price
$141
Highest Price
$648

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