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Search results; Over 1,000 homes in Pine Plains

Top guest favourite
Cottage in Pine Plains
Patchin Mills Quaint Country Cottage
2 bedrooms, 2 beds, 1 private bathroom
31 Aug – 5 Sept
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5.0 out of 5 average rating, 163 reviews
Top guest favourite
Flat in Pine Plains
Newly renovated cutie
4.97 out of 5 average rating, 264 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
Guest favourite
Room in Town of Ancram
The Doodletown
4.96 out of 5 average rating, 207 reviews, 1 double bed, 1 bathroom
6–11 Jul
Guest house in Pine Plains
Cozy Country Cottage in Pine Plains
1 bedroom, 1 bed, 1 bathroom
13–18 Jul
Top guest favourite
Home in Pine Plains
Hudson Valley Retreat: Pool, Views, Chef's Kitchen
5.0 out of 5 average rating, 11 reviews, 5 bedrooms, 6 beds, 5.5 bathrooms
6–11 Jul
Top guest favourite
Island in Pine Plains
Magical Private Island Retreat in Pine Plains
4.97 out of 5 average rating, 103 reviews, 1 bedroom, 3 beds, 1 bathroom
5–10 Jul
Top guest favourite
Farm stay in Town of Ancram
Relaxing secluded stay with loving social animals.
4.96 out of 5 average rating, 393 reviews, 2 beds, 1 bathroom
2–7 Aug
Guest favourite
Home in Pine Plains
Stunningly Designed Historical Icon w/ Hot Tub
4.95 out of 5 average rating, 20 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
5–10 Jul
Top guest favourite
Guest suite in Red Hook
the farmhouse suite @barn & bike
4.93 out of 5 average rating, 448 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 Jul
Top guest favourite
Home in Pine Plains
Twin Island Lake House • Hot Tub
4.99 out of 5 average rating, 138 reviews, 3 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
Top guest favourite
Home in Red Hook
Bee Kind Cottage
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 1 bed, 3 bathrooms
17–22 Jul
Superhost
Room in Pine Plains
The Smithfield Room
4.73 out of 5 average rating, 11 reviews, 1 bed, 1 bathroom
5–10 Jul
Superhost
Home in Pine Plains
NEW: Chic Modern Barn Style Home in Fun Area
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
10–15 Jul
Top guest favourite
Cottage in Red Hook
bright serene + spacious barn @barn and bike
4.98 out of 5 average rating, 738 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
18–23 Jul
Guest favourite
Island in Pine Plains
Private Island on Twin Island Lake
4.94 out of 5 average rating, 94 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Top guest favourite
Room in Red Hook
Guest suite near Omega Institute and Rhinebeck
4.93 out of 5 average rating, 42 reviews, 1 queen bed, 1 bathroom
24–29 Aug
Top guest favourite
Guest suite in Red Hook
Panoramic Mountain Views!
4.99 out of 5 average rating, 104 reviews, 1 bedroom, 4 beds, 1 bathroom
21–26 Jul
Top 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
4–9 Aug