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Search results; Over 1,000 homes in Pine Plains

Guest favourite
Cottage in Pine Plains
Pine Plains Cottage
2 bedrooms, 3 beds, 1 private bathroom
14–19 Aug
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4.96 out of 5 average rating, 163 reviews
Guest favourite
Flat in Pine Plains
Newly renovated cutie
4.96 out of 5 average rating, 268 reviews, 1 bedroom, 1 bed, 1 bathroom
2–7 Aug
Guest favourite
Guest house in Pine Plains
Cozy Country Cottage in Pine Plains
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Aug
Top guest favourite
Island in Pine Plains
Magical Private Island Retreat in Pine Plains
4.97 out of 5 average rating, 104 reviews, 1 bedroom, 3 beds, 1 bathroom
18–23 Aug
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
Guest favourite
Room in Town of Ancram
The Doodletown
4.96 out of 5 average rating, 210 reviews, 1 double bed, 1 bathroom
10–15 Aug
Home in Pine Plains
Polo Field Farmhouse
New place to stay, 4 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
Superhost
Home in Pine Plains
NEW: Chic Modern Barn Style Home in Fun Area
3 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
Superhost
Room in Pine Plains
The Smithfield Room
4.73 out of 5 average rating, 11 reviews, 1 bed, 1 bathroom
31 Aug – 5 Sept
Guest favourite
Island in Pine Plains
Private Island on Twin Island Lake
4.94 out of 5 average rating, 96 reviews, 1 bedroom, 1 bed, 1 bathroom
11–16 Sept
Top guest favourite
Room in Red Hook
Cozy BR near Rhinebeck, Omega, Bard - Fox Rm
5.0 out of 5 average rating, 10 reviews, 1 double bed, 1 bathroom
1–6 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
1–6 Aug
Guest favourite
Cottage in Town of Ancram
Chic Country Home on 5 acres | Hudson 20 min
4.91 out of 5 average rating, 90 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
1–6 Aug
Top guest favourite
Guest suite in Red Hook
the farmhouse suite @barn & bike
4.93 out of 5 average rating, 452 reviews, 1 bedroom, 1 bed, 1 bathroom
19–24 Aug
Barn in Pine Plains
Stunning Horse Farm Apt With Hot Tub
1 bedroom, 1 bed, 1 bathroom
18–23 Aug
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
18–23 Aug
Top guest favourite
Guest suite in Red Hook
Panoramic Mountain Views!
4.99 out of 5 average rating, 109 reviews, 1 bedroom, 4 beds, 1 bathroom
1–6 Aug
Top guest favourite
Home in Town of Ancram
Grandma's country house. Skiing / Fishing/ Hiking
4.97 out of 5 average rating, 35 reviews, 3 bedrooms, 4 beds, 2 bathrooms
1–6 Aug
Top guest favourite
Home in Pine Plains
Hudson Valley Retreat: Pool, Views, Chef's Kitchen
5.0 out of 5 average rating, 12 reviews, 5 bedrooms, 6 beds, 5.5 bathrooms
20–25 Oct