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Search results; Over 1,000 homes in Pine Plains

Top guest favourite
Island in Pine Plains
Magical Private Island Retreat in Pine Plains
1 bedroom, 3 beds, 1 private bathroom
19–24 Jul
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4.97 out of 5 average rating, 104 reviews
Top guest favourite
Cottage in Pine Plains
Patchin Mills Quaint Country Cottage
5.0 out of 5 average rating, 165 reviews, 2 bedrooms, 2 beds, 1 bathroom
31 Aug – 5 Sept
Top guest favourite
Flat in Pine Plains
Newly renovated cutie
4.97 out of 5 average rating, 267 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Home in Pine Plains
Polo Field Farmhouse
New place to stay, 4 bedrooms, 5 beds, 2 bathrooms
16–21 Jul
Top guest favourite
Home in Pine Plains
Stunningly Designed Luxury Home w/ Pool & Hot Tub
5.0 out of 5 average rating, 56 reviews, 3 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Pine Plains
Twin Island Lake House • Hot Tub
4.99 out of 5 average rating, 139 reviews, 3 bedrooms, 4 beds, 2 bathrooms
10–15 Sept
Superhost
Home in Pine Plains
NEW: Chic Modern Barn Style Home in Fun Area
3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Guest favourite
Home in Pine Plains
Stunningly Designed Historical Icon w/ Hot Tub
4.95 out of 5 average rating, 22 reviews, 3 bedrooms, 3 beds, 3 bathrooms
13–18 Sept
Guest favourite
Home in Pine Plains
Silo-country home steeped with delicious touches.
4.96 out of 5 average rating, 57 reviews, 5 bedrooms, 9 beds, 2.5 bathrooms
18–23 Jul
Top guest favourite
Guest suite in Red Hook
the farmhouse suite @barn & bike
4.93 out of 5 average rating, 450 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Superhost
Room in Pine Plains
The Smithfield Room
4.73 out of 5 average rating, 11 reviews, 1 bed, 1 bathroom
26–31 Jul
Guest favourite
Room in Town of Ancram
The Doodletown
4.96 out of 5 average rating, 208 reviews, 1 double bed, 1 bathroom
24–29 Jul
Guest favourite
Island in Pine Plains
Private Island on Twin Island Lake
4.94 out of 5 average rating, 95 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Sept
Barn in Pine Plains
Stunning Horse Farm Apt With Hot Tub
1 bedroom, 1 bed, 1 bathroom
19–24 Jul
Top guest favourite
Cottage in Red Hook
bright serene + spacious barn @barn and bike
4.98 out of 5 average rating, 740 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
4–9 Sept
Top guest favourite
Home in Pine Plains
Family home with pond
5.0 out of 5 average rating, 22 reviews, 5 bedrooms, 5 beds, 4.5 bathrooms
4–9 Aug
Top guest favourite
Home in Pine Plains
Stony Hill Haus in Pine Plains
5.0 out of 5 average rating, 25 reviews, 4 bedrooms, 5 beds, 3.5 bathrooms
27 Jul – 1 Aug
Guest favourite
Home in Pine Plains
Hudson Valley Farmhouse on a Country Lane
4.93 out of 5 average rating, 91 reviews, 2 bedrooms, 2 beds, 2 bathrooms
2–7 Sept
Top guest favourite
Cottage in Red Hook
Creekside Cottage | The Fitz House Red Hook NY
4.98 out of 5 average rating, 113 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Aug