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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
14–19 Sept
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5.0 out of 5 average rating, 171 reviews
Guest favourite
Flat in Pine Plains
Newly renovated cutie
1 bedroom, 1 bed
14–19 Sept
4.96 out of 5 average rating, 286 reviews
Guest favourite
Barn in Pine Plains
The Nook - An Adorable Secret Get Away
1 bed
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
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
14–19 Sept
4.93 out of 5 average rating, 92 reviews
Top guest favourite
Island in Pine Plains
Magical Private Island Retreat in Pine Plains
1 bedroom, 3 beds
30 Sept – 5 Oct
4.97 out of 5 average rating, 111 reviews
Superhost
Room in Pine Plains
The Smithfield Room
1 bed
31 Oct – 5 Nov
4.75 out of 5 average rating, 12 reviews
Top guest favourite
Home in Red Hook
Taconic Hill-a modern retreat on 50 forested acres
4 bedrooms, 6 beds
12–17 Sept
4.95 out of 5 average rating, 42 reviews
Top guest favourite
Guest suite in Red Hook
the farmhouse suite @barn & bike
1 bedroom, 1 queen bed
12–17 Sept
4.93 out of 5 average rating, 457 reviews
Guest favourite
Home in Town of Ancram
Modern Scandinavian Farmhouse w/ Vintage Camper
2 bedrooms, 2 beds
21–26 Sept
5.0 out of 5 average rating, 70 reviews
Guest favourite
Flat in Red Hook
Secluded Hideaway Gem
1 bedroom, 1 bed
2–7 Nov
4.91 out of 5 average rating, 55 reviews
Home in Pine Plains
Polo Field Farmhouse
4 bedrooms, 5 beds
15–20 Sept
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Rhinebeck
Lush Retreat Near Rhinebeck
3 bedrooms, 4 beds
13–18 Sept
4.93 out of 5 average rating, 61 reviews
Top guest favourite
Home in Town of Ancram
Warm Sunny Days Are Still Here To Be Enjoyed
3 bedrooms, 4 beds
10–15 Sept
4.99 out of 5 average rating, 173 reviews
Top guest favourite
Home in Pine Plains
Family home with pond
5 bedrooms, 5 beds
27 Oct – 1 Nov
5.0 out of 5 average rating, 25 reviews
Guest favourite
Farm stay in Town of Ancram
Private Farmstay & Forest Spa Near Hudson
2 beds
25–30 Oct
4.96 out of 5 average rating, 408 reviews
Top guest favourite
Home in Rhinebeck
Slate Cabin - Stylish Country Escape x Rhinebeck
3 bedrooms, 3 queen beds
28 Sept – 3 Oct
4.98 out of 5 average rating, 131 reviews
Guest favourite
Home in Pine Plains
Stunningly Designed Historical Icon w/ Hot Tub
3 bedrooms, 3 beds
13–18 Sept
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Cabin in Red Hook
Modern Upstate Cabin, near Rhinebeck NY
1 bedroom, 1 queen bed
14–19 Sept
4.96 out of 5 average rating, 397 reviews