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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
5–10 Jul
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4.97 out of 5 average rating, 103 reviews
Top guest favourite
Cottage in Pine Plains
Patchin Mills Quaint Country Cottage
5.0 out of 5 average rating, 163 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, 264 reviews, 1 bedroom, 1 bed, 1 bathroom
12–17 Jul
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 house in Pine Plains
Cozy Country Cottage in Pine Plains
1 bedroom, 1 bed, 1 bathroom
13–18 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
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
Home in Pine Plains
Stunningly Designed Luxury Home w/ Pool & Hot Tub
5.0 out of 5 average rating, 52 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, 138 reviews, 3 bedrooms, 4 beds, 2 bathrooms
7–12 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
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
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
Superhost
Room in Pine Plains
The Smithfield Room
4.73 out of 5 average rating, 11 reviews, 1 bed, 1 bathroom
5–10 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
Home in Rhinebeck
Eagle Rock House
5.0 out of 5 average rating, 255 reviews, 3 bedrooms, 3 beds, 2.5 bathrooms
18–23 Jul
Top guest favourite
Home in Pine Plains
Family-Friendly by Polo + EV Chgr
4.96 out of 5 average rating, 24 reviews, 3 bedrooms, 5 beds, 2 bathrooms
25–30 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
Guest favourite
Home in Pine Plains
Hudson Valley Farmhouse on a Country Lane
4.93 out of 5 average rating, 90 reviews, 2 bedrooms, 2 beds, 2 bathrooms
2–7 Sept
Top guest favourite
Home in Red Hook
Private 120-Acre Escape | Hot Tub, River & Firepit
5.0 out of 5 average rating, 32 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
12–17 Jul