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Search results; Over 1,000 homes in Pine Plains

Top guest favourite
Cabin in Pine Plains
The Upstate A - Modern Luxury in the Hudson Valley
4 bedrooms, 4 beds, 2.5 private bathrooms
30 Aug – 4 Sept
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4.97 out of 5 average rating, 297 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, 274 reviews
Cabin in Pine Plains
Robin's Nest: Cozy Lakeside Cottage in Pine Plains
2 bedrooms, 3 beds, 1 bathroom
6–11 Sept
5.0 out of 5 average rating, 4 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, 189 reviews
Superhost
Home in Pine Plains
NEW: Chic Modern Barn Style Home in Fun Area
3 bedrooms, 3 beds, 2 bathrooms
16–21 Aug
5.0 out of 5 average rating, 3 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, 7 reviews
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
Top guest favourite
Island in Pine Plains
Magical Private Island Retreat in Pine Plains
1 bedroom, 3 beds, 1 bathroom
15–20 Sept
4.97 out of 5 average rating, 108 reviews
Barn in Pine Plains
Stunning Horse Farm Apt With Hot Tub
1 bedroom, 1 king bed, 1 bathroom
23–28 Aug
Guest favourite
Room in Town of Ancram
The Doodletown
1 double bed, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 214 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, 22 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
Guest suite in Red Hook
Cozy 1 bedroom walkout on 6 acres. Sleeps 3
1 bedroom, 2 single beds, 1 bathroom
26–31 Aug
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Guest house in Germantown
The Loft
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 265 reviews
Guest favourite
Home in Millerton
Peaceful Farmhouse w/ Views + Rail Trail Access
3 bedrooms, 4 beds, 1.5 bathrooms
14–19 Sept
4.92 out of 5 average rating, 26 reviews
Top guest favourite
Guest suite in Salisbury
Bright & Airy Guest Suite
1 bedroom, 1 queen bed, 1 bathroom
9–14 Sept
5.0 out of 5 average rating, 45 reviews
Guest favourite
Flat in Red Hook
Secluded Hideaway Gem
1 bedroom, 1 bed, 1 bathroom
18–23 Aug
4.92 out of 5 average rating, 53 reviews