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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
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
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
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
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
6–11 Sept
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
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
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
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
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
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, 748 reviews
Guest favourite
Home in Town of Taghkanic
Wildflower Cottage near Hudson w/ Fire Pit & AC
3 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 21 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 Millerton
Peaceful Farmhouse w/ Views + Rail Trail Access
3 bedrooms, 4 beds, 1.5 bathrooms
14–19 Sept
4.93 out of 5 average rating, 27 reviews
Top guest favourite
Room in Poughkeepsie
Hudson Pond · Garden Queen Suite · GF Breakfast
1 queen bed, 1 bathroom
11–16 Sept
4.99 out of 5 average rating, 170 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
Flat in Egremont
Berkshires Charm Private Apartment
1 bedroom, 1 queen bed, 1 bathroom
18–23 Oct
New place to stay
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