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Search results; Over 1,000 homes in Pine Plains

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Guest favourite
Home in Pine Plains
Stunningly Designed Historical Icon w/ Hot Tub
3 bedrooms, 3 beds, 3 private bathrooms
19–24 Sept
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4.96 out of 5 average rating, 24 reviews
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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
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Top guest favourite
Flat in Pine Plains
Newly renovated cutie
1 bedroom, 1 bed
26–31 Oct
4.96 out of 5 average rating, 287 reviews
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Top guest favourite
Cottage in Pine Plains
Patchin Mills Quaint Country Cottage
2 bedrooms, 2 beds
20–25 Oct
5.0 out of 5 average rating, 172 reviews
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Home in Pine Plains
Polo Field Farmhouse
4 bedrooms, 5 beds
19–24 Sept
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Home in Pine Plains
Hudson Valley Farmhouse on a Country Lane
2 bedrooms, 2 queen beds
22–27 Sept
4.93 out of 5 average rating, 92 reviews
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Home in Pine Plains
Polo Field Family Home | Games & EV Charger
3 bedrooms, 5 beds
19–24 Sept
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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
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Top guest favourite
Home in Pine Plains
Stony Hill Haus in Pine Plains
4 bedrooms, 5 beds
5–10 Oct
5.0 out of 5 average rating, 27 reviews
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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, 12 reviews
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Top guest favourite
Home in Pine Plains
Hudson Valley Retreat: Pool, Views, Chef's Kitchen
5 bedrooms, 6 beds
20–25 Oct
5.0 out of 5 average rating, 16 reviews
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Top guest favourite
Island in Pine Plains
Magical Private Island Retreat in Pine Plains
1 bedroom, 3 beds
26–31 Oct
4.97 out of 5 average rating, 113 reviews
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Superhost
Room in Pine Plains
The Smithfield Room
1 bed
31 Oct – 5 Nov
4.75 out of 5 average rating, 12 reviews
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Top guest favourite
Home in Millerton
The 1913 House, book 6 days get the 7th free.
3 bedrooms, 4 beds
20–25 Sept
4.9 out of 5 average rating, 184 reviews
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Top guest favourite
Home in Stanfordville
Hilltop Hideaway- fire pit, hot tub, mountain view
3 bedrooms, 4 beds
18–23 Oct
5.0 out of 5 average rating, 40 reviews
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Top guest favourite
Home in Pine Plains
Stunningly Designed Luxury Home w/ Pool & Hot Tub
3 bedrooms, 3 beds
23–28 Nov
5.0 out of 5 average rating, 62 reviews
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Home in Millerton
The House in a Beautiful Small Upstate Town
4 bedrooms, 6 beds
20–25 Sept
4.97 out of 5 average rating, 266 reviews
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Home in Red Hook
Taconic Hill-a modern retreat on 50 forested acres
4 bedrooms, 6 beds
21–26 Sept
4.95 out of 5 average rating, 42 reviews
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Top guest favourite
Home in Red Hook
River Nest
3 bedrooms, 4 beds
19–24 Sept
4.94 out of 5 average rating, 16 reviews