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Search results; Over 1,000 homes in Pine Plains

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Top guest favourite
Flat in Pine Plains
Newly renovated cutie
1 bedroom, 1 bed, 1 private bathroom
1–6 Nov
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4.96 out of 5 average rating, 289 reviews
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Home in Pine Plains
Polo Field Farmhouse
4 bedrooms, 5 beds, 2 bathrooms
18–23 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Barn in Pine Plains
The Nook - An Adorable Secret Get Away
1 bed, 1 bathroom
1–6 Nov
4.98 out of 5 average rating, 191 reviews
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Top guest favourite
Cottage in Pine Plains
Patchin Mills Quaint Country Cottage
2 bedrooms, 2 beds, 1 bathroom
27 Oct – 1 Nov
5.0 out of 5 average rating, 172 reviews
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Top guest favourite
Guest house in Pine Plains
Cozy Country Cottage in Pine Plains
1 bedroom, 1 king bed, 1 bathroom
19–24 Oct
5.0 out of 5 average rating, 12 reviews
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Home in Pine Plains
Polo Field Family Home | Games & EV Charger
3 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
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Guest favourite
Home in Pine Plains
Hudson Valley Farmhouse on a Country Lane
2 bedrooms, 2 queen beds, 2 bathrooms
26–31 Oct
4.93 out of 5 average rating, 92 reviews
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Guest favourite
Home in Pine Plains
Stunningly Designed Historical Icon w/ Hot Tub
3 bedrooms, 3 beds, 3 bathrooms
11–16 Oct
4.96 out of 5 average rating, 24 reviews
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Top guest favourite
Home in Pine Plains
Family home with pond
5 bedrooms, 5 beds, 4.5 bathrooms
27 Oct – 1 Nov
5.0 out of 5 average rating, 25 reviews
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Top guest favourite
Home in Pine Plains
Hudson Valley Retreat: Pool, Views, Chef's Kitchen
5 bedrooms, 6 beds, 5.5 bathrooms
20–25 Oct
5.0 out of 5 average rating, 16 reviews
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Superhost
Room in Pine Plains
The Smithfield Room
1 bed, 1 bathroom
31 Oct – 5 Nov
4.75 out of 5 average rating, 12 reviews
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Top guest favourite
Island in Pine Plains
Magical Private Island Retreat in Pine Plains
1 bedroom, 3 beds, 1 bathroom
26–31 Oct
4.97 out of 5 average rating, 113 reviews
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Top guest favourite
Home in Millerton
The House in a Beautiful Small Upstate Town
4 bedrooms, 6 beds, 3 bathrooms
25–30 Oct
4.97 out of 5 average rating, 268 reviews
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Guest favourite
Home in Rhinebeck
3Br Hilltop Ranch on 130acre farm w/ falls & creek
3 bedrooms, 4 beds, 2 bathrooms
27 Nov – 2 Dec
4.95 out of 5 average rating, 307 reviews
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Top guest favourite
Home in Pine Plains
Stony Hill Haus in Pine Plains
4 bedrooms, 5 beds, 3.5 bathrooms
5–10 Oct
5.0 out of 5 average rating, 27 reviews
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Guest favourite
Room in Town of Ancram
The Doodletown
1 double bed, 1 bathroom
1–6 Oct
4.96 out of 5 average rating, 218 reviews
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Cottage in Red Hook
Tranquil & Private Cottage in Gallatin
3 bedrooms, 3 beds, 2 bathrooms
1–6 Feb
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Home in Millerton
Peaceful Farmhouse w/ Views + Rail Trail Access
3 bedrooms, 4 beds, 1.5 bathrooms
26–31 Oct
4.94 out of 5 average rating, 31 reviews
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Top guest favourite
Cabin in Red Hook
Luxury Scandi Lakeside Cabin with Woodfired Sauna
3 bedrooms, 4 beds, 2 bathrooms
9–14 Nov
5.0 out of 5 average rating, 18 reviews