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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, 296 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, 273 reviews
Cabin in Pine Plains
Robin's Nest: Cozy Lakeside Cottage in Pine Plains
2 bedrooms, 3 beds, 1 bathroom
29 Aug – 3 Sept
5.0 out of 5 average rating, 4 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
31 Aug – 5 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
15–20 Sept
5.0 out of 5 average rating, 7 reviews
Home in Pine Plains
Polo Field Farmhouse
4 bedrooms, 5 beds, 2 bathrooms
11–16 Aug
New place to stay
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
Barn in Pine Plains
Stunning Horse Farm Apt With Hot Tub
1 bedroom, 1 king bed, 1 bathroom
23–28 Aug
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
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, 106 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
Guest favourite
Home in Pine Plains
Silo-country home steeped with delicious touches.
5 bedrooms, 9 beds, 2.5 bathrooms
18–23 Aug
4.96 out of 5 average rating, 57 reviews
Top guest favourite
Room in Poughkeepsie
Hudson Pond · Hideaway King Suite · GF Breakfast
1 king bed, 1 bathroom
26–31 Aug
4.97 out of 5 average rating, 243 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, 745 reviews
Guest favourite
Cabin in Town of Ancram
Architectural Cabin, 2 bed, near Taghkanic Lake
1 bedroom, 2 queen beds, 1 bathroom
22–27 Aug
4.98 out of 5 average rating, 49 reviews
Top guest favourite
Room in Hyde Park
Scandinavian Design Dutchess County - 1 of 3 rooms
1 king bed, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 689 reviews
Guest favourite
Room in Town of Ancram
The Doodletown
1 double bed, 1 bathroom
17–22 Aug
4.96 out of 5 average rating, 212 reviews
Top guest favourite
Home in Pine Plains
Stunningly Designed Luxury Home w/ Pool & Hot Tub
3 bedrooms, 3 beds, 2 bathrooms
29 Aug – 3 Sept
5.0 out of 5 average rating, 59 reviews