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
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
Guest house in Pine Plains
Cozy Country Cottage in Pine Plains
1 bedroom, 1 bed, 1 bathroom
13–18 Jul
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
3–8 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
Home in Pine Plains
Family home with pond
5.0 out of 5 average rating, 21 reviews, 5 bedrooms, 5 beds, 4.5 bathrooms
4–9 Aug
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
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 Millerton
The House in a Beautiful Small Upstate Town
4.97 out of 5 average rating, 258 reviews, 4 bedrooms, 7 beds, 3 bathrooms
20–25 Sept
Top guest favourite
Cottage in Red Hook
bright serene + spacious barn @barn and bike
4.98 out of 5 average rating, 737 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
18–23 Jul
Top guest favourite
Cabin in Clinton Corners
Pinefeather Lodge Nature Escape with Pool & Yoga
5.0 out of 5 average rating, 24 reviews, 6 bedrooms, 11 beds, 5 bathrooms
1–6 Aug
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
Top guest favourite
Loft in Stanfordville
Harley's Hideaway - Cozy Furnished Apartment
4.99 out of 5 average rating, 125 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 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
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 Red Hook
River Nest
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Sept
Top guest favourite
Farm stay in Town of Ancram
Relaxing secluded stay with loving social animals.
4.96 out of 5 average rating, 392 reviews, 2 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Red Hook
Tranquil & Private River Home
5.0 out of 5 average rating, 34 reviews, 3 bedrooms, 3 beds, 2 bathrooms
31 Aug – 5 Sept