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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
Guest house in Pine Plains
Cozy Country Cottage in Pine Plains
1 bedroom, 1 bed, 1 bathroom
13–18 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
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
2–7 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
Cottage in Red Hook
bright serene + spacious barn @barn and bike
4.98 out of 5 average rating, 736 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
18–23 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
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
Guest suite in Red Hook
the farmhouse suite @barn & bike
4.93 out of 5 average rating, 447 reviews, 1 bedroom, 1 bed, 1 bathroom
17–22 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 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
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
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
Home in Staatsburg
Boulder Tree House
4.99 out of 5 average rating, 131 reviews, 1 bedroom, 2 beds, 2 bathrooms
6–11 Aug
Cottage in Dover Plains
Fallerhof – Millbrook Retreat on 150 Private Acres
2 bedrooms, 2 beds, 1 bathroom
4–9 Jul
Cabin in Mount Washington
Chic Cabin in the Berkshires, Mountain getaway!
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 2 beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Stanfordville
Hilltop Hideaway- fire pit, hot tub, mountain view
5.0 out of 5 average rating, 34 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
Home in Hudson
9 Acre Hudson retreat- private pond-sleeps 10
New place to stay, 3 bedrooms, 7 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Cabin in Catskill
Riverside Retreat on the Hudson - Modern Cottage
4.99 out of 5 average rating, 182 reviews, 2 bedrooms, 2 beds, 1 bathroom
5–10 Jul