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Search results; Over 1,000 homes in Pine Plains

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Room in Pine Plains
The Smithfield Room
1 bedroom, 1 bed, 1 bathroom
31 Aug – 5 Sept
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4.75 out of 5 average rating, 12 reviews
Cabin in Pine Plains
Robin's Nest: Cozy Lakeside Cottage in Pine Plains
2 bedrooms, 3 beds, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Flat in Pine Plains
Newly renovated cutie
1 bedroom, 1 bed, 1 bathroom
31 Aug – 5 Sept
4.96 out of 5 average rating, 276 reviews
Top guest favourite
Cottage in Pine Plains
Patchin Mills Quaint Country Cottage
2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 168 reviews
Home in Pine Plains
Polo Field Farmhouse
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 3 reviews
Guest favourite
Guest house in Pine Plains
Cozy Country Cottage in Pine Plains
1 bedroom, 1 king bed, 1 bathroom
25–30 Aug
5.0 out of 5 average rating, 8 reviews
Barn in Pine Plains
Stunning Horse Farm Apt With Hot Tub
1 bedroom, 1 king bed, 1 bathroom
23–28 Aug
Guest favourite
Home in Pine Plains
Hudson Valley Farmhouse on a Country Lane
2 bedrooms, 2 queen beds, 2 bathrooms
2–7 Sept
4.93 out of 5 average rating, 91 reviews
Top guest favourite
Island in Pine Plains
Magical Private Island Retreat in Pine Plains
1 bedroom, 3 beds, 1 bathroom
30 Sept – 5 Oct
4.97 out of 5 average rating, 108 reviews
Top guest favourite
Home in Pine Plains
Family home with pond
5 bedrooms, 5 beds, 4.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 23 reviews
Guest favourite
Home in Pine Plains
Silo-country home steeped with delicious touches.
5 bedrooms, 9 beds, 2.5 bathrooms
1–6 Sept
4.96 out of 5 average rating, 57 reviews
Guest favourite
Home in Pine Plains
Stunningly Designed Historical Icon w/ Hot Tub
3 bedrooms, 3 beds, 3 bathrooms
29 Aug – 3 Sept
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Cottage in Red Hook
bright serene + spacious barn @barn and bike
2 bedrooms, 4 beds, 1.5 bathrooms
21–26 Sept
4.98 out of 5 average rating, 747 reviews
Top guest favourite
Home in Red Hook
Bee Kind Cottage
3 bedrooms, 1 queen bed, 3 bathrooms
20–25 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Cabin in Red Hook
Design-Forward Riverfront Cabin on 120 Acres
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 133 reviews
Top guest favourite
Home in Rhinebeck
3Br Hilltop Ranch on 130acre farm w/ falls & creek
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.95 out of 5 average rating, 300 reviews
Top guest favourite
Home in Rhinebeck
Slate Cabin - Stylish Country Escape x Rhinebeck
3 bedrooms, 3 queen beds, 2 bathrooms
8–13 Nov
4.98 out of 5 average rating, 130 reviews
Top guest favourite
Home in Highland
VIEWS on Hudson River / Luxury Modern Home
4 bedrooms, 5 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 8 reviews
Home in Gallatin
Orchard House: a dreamy, country farmhouse
2 bedrooms, 2 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 4 reviews