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Search results; Over 1,000 homes in Pine Plains

Guest favourite
Flat in Pine Plains
Newly renovated cutie
1 bedroom, 1 bed, 1 bathroom
26–31 Oct
4.96 out of 5 average rating, 286 reviews
Top guest favourite
Cottage in Pine Plains
Patchin Mills Quaint Country Cottage
2 bedrooms, 2 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 171 reviews
Guest favourite
Barn in Pine Plains
The Nook - An Adorable Secret Get Away
1 bed, 1 bathroom
21–26 Oct
4.98 out of 5 average rating, 191 reviews
Top guest favourite
Guest house in Pine Plains
Cozy Country Cottage in Pine Plains
1 bedroom, 1 king bed, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Pine Plains
Hudson Valley Farmhouse on a Country Lane
2 bedrooms, 2 queen beds, 2 bathrooms
15–20 Sept
4.93 out of 5 average rating, 92 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, 18 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, 111 reviews
Superhost
Room in Pine Plains
The Smithfield Room
1 bed, 1 bathroom
31 Oct – 5 Nov
4.75 out of 5 average rating, 12 reviews
Home in Stanfordville
Chic Lakeside Oasis | Near Rhinebeck & Millbrook
3 bedrooms, 3 beds, 3 bathrooms
21–26 Sept
New place to stay
Guest favourite
Flat in Red Hook
Secluded Hideaway Gem
1 bedroom, 1 bed, 1 bathroom
2–7 Nov
4.91 out of 5 average rating, 55 reviews
Guest favourite
Home in Town of Ancram
Modern Scandinavian Farmhouse w/ Vintage Camper
2 bedrooms, 2 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 70 reviews
Top guest favourite
Home in Red Hook
Taconic Hill-a modern retreat on 50 forested acres
4 bedrooms, 6 beds, 3 bathrooms
14–19 Sept
4.95 out of 5 average rating, 42 reviews
Home in Pine Plains
Polo Field Family Home | Games & EV Charger
3 bedrooms, 5 beds, 2 bathrooms
13–18 Sept
New place to stay
Guest favourite
Home in Rhinebeck
Lush Retreat Near Rhinebeck
3 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
4.93 out of 5 average rating, 61 reviews
Home in Pine Plains
Polo Field Farmhouse
4 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest suite in Red Hook
the farmhouse suite @barn & bike
1 bedroom, 1 queen bed, 1 bathroom
28 Oct – 2 Nov
4.93 out of 5 average rating, 457 reviews
Home in Town of Hillsdale
Lakefront Escape w/ Dock! Hudson Valley Home
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Guest house in Pine Plains
Cozy Cottage by the Pond
1 bedroom, 1 double bed, 1 bathroom
27 Oct – 1 Nov
4.98 out of 5 average rating, 82 reviews