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Search results; Over 1,000 homes in Pine Plains

Guest favourite
Home in Pine Plains
The Blue Roof Barn In The Beautiful Hudson Valley
2 bedrooms, 5 beds, 1.5 private bathrooms
16–21 Aug
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4.74 out of 5 average rating, 50 reviews
Guest favourite
Flat in Pine Plains
Newly renovated cutie
1 bedroom, 1 bed
31 Aug – 5 Sept
4.96 out of 5 average rating, 272 reviews
Cabin in Pine Plains
Robin's Nest: Cozy Lakeside Cottage in Pine Plains
2 bedrooms, 3 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Pine Plains
NEW: Chic Modern Barn Style Home in Fun Area
3 bedrooms, 3 beds
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Guest house in Pine Plains
Cozy Country Cottage in Pine Plains
1 bedroom, 1 king bed
15–20 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Cottage in Pine Plains
Patchin Mills Quaint Country Cottage
2 bedrooms, 2 beds
31 Aug – 5 Sept
5.0 out of 5 average rating, 168 reviews
Home in Pine Plains
Polo Field Farmhouse
4 bedrooms, 5 beds
10–15 Aug
New place to stay
Top guest favourite
Island in Pine Plains
Magical Private Island Retreat in Pine Plains
1 bedroom, 3 beds
15–20 Sept
4.97 out of 5 average rating, 106 reviews
Guest favourite
Home in Pine Plains
Hudson Valley Farmhouse on a Country Lane
2 bedrooms, 2 queen beds
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
23–28 Aug
Top guest favourite
Home in Pine Plains
Family home with pond
5 bedrooms, 5 beds
14–19 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
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
18–23 Aug
4.96 out of 5 average rating, 57 reviews
Top guest favourite
Cottage in Red Hook
bright serene + spacious barn @barn and bike
2 bedrooms, 4 beds
21–26 Sept
4.98 out of 5 average rating, 745 reviews
Top guest favourite
Cottage in Pine Plains
Peacock Garden Cottage
2 bedrooms, 4 beds
1–6 Oct
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Home in Pine Plains
Stunningly Designed Luxury Home w/ Pool & Hot Tub
3 bedrooms, 3 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 58 reviews
Top guest favourite
Camper van/Motorhome in Wassaic
Glamp in a 1970s Airstream | Hot Tub | NYC Train
3 beds
23–28 Aug
4.99 out of 5 average rating, 96 reviews
Top guest favourite
Rooms in Tivoli
Suminski Innski - Room 4 Queen bed/shared bath
2 bedrooms, 1 queen bed
23–28 Aug
4.88 out of 5 average rating, 253 reviews
Guest favourite
Room in Town of Ancram
The Doodletown
1 double bed
17–22 Aug
4.96 out of 5 average rating, 212 reviews