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Search results; Over 1,000 homes in Pine Plains

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Top guest favourite
Island in Pine Plains
Magical Private Island Retreat in Pine Plains
1 bedroom, 3 beds, 1 private bathroom
26–31 Oct
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4.97 out of 5 average rating, 113 reviews
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Top guest favourite
Flat in Pine Plains
Newly renovated cutie
1 bedroom, 1 bed, 1 bathroom
1–6 Nov
4.96 out of 5 average rating, 290 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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Guest favourite
Cabin in Pine Plains
Robin's Nest: Cozy Lakeside Cottage in Pine Plains
2 bedrooms, 3 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 5 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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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
Home in Pine Plains
Hudson Valley Farmhouse on a Country Lane
2 bedrooms, 2 queen beds, 2 bathrooms
19–24 Oct
4.93 out of 5 average rating, 92 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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Home in Pine Plains
Polo Field Family Home | Games & EV Charger
3 bedrooms, 5 beds, 2 bathrooms
27 Oct – 1 Nov
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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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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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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
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
5–10 Oct
4.96 out of 5 average rating, 218 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
26–31 Oct
5.0 out of 5 average rating, 13 reviews
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Top guest favourite
Cottage in Pine Plains
Peacock Garden Cottage
2 bedrooms, 4 beds, 1 bathroom
11–16 Oct
4.92 out of 5 average rating, 25 reviews
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Top guest favourite
Home in Red Hook
Hudson Valley | Hot Tub + 120 Acres + Fire Pit
3 bedrooms, 6 beds, 2.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 45 reviews
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Guest favourite
Flat in Red Hook
Secluded Hideaway Gem
1 bedroom, 1 bed, 1 bathroom
27 Oct – 1 Nov
4.91 out of 5 average rating, 55 reviews
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Guest house in Pine Plains
Charming 2 bedroom Stissing Lake Guest Cottage
2 bedrooms, 5 beds, 2 bathrooms
1–6 Oct
4.57 out of 5 average rating, 30 reviews