Over 1,000 homes

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Superhost
Tiny home in Chatham
Sugar Shack - 300 square feet of pure sweetness.
2 beds
Oct 16 – 21
$213 per night
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Superhost
Cottage in Hillsdale
Big Bliss Near Catamount Cottage w/Modern Flair
3 beds
Oct 1 – 8
$127 per night, originally $149
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Superhost
Guest suite in Valatie
Guest Suite in Old Chatham Hunt Country
1 queen bed
Oct 11 – 16
$86 per night, originally $95
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Home in Kinderhook
The Big Yard at Kinderhook
3 beds
Oct 1 – 6
$204 per night, originally $240
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Superhost
Cottage in Kinderhook
Private + Peaceful Refuge from the Big City
2 beds
Oct 1 – 6
$128 per night, originally $148
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Home in Hudson
19th Century Mill House with River View
3 beds
Oct 1 – 6
$159 per night
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Superhost
Cabin in Chatham
The Upstate Cabin: A secluded getaway in the woods
2 queen beds
Oct 26 – Nov 1
$405 per night
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Superhost
Home in New Lebanon
The old sawmill from 1771
2 beds
Oct 1 – 6
$122 per night
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Superhost
Barn in Kinderhook
Unique Village Antique Print/Shop Studio Apartment
2 beds
Oct 16 – 21
$101 per night
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Superhost
Home in Old Chatham
Secluded House in Historic Old Chatham, NY
5 beds
Nov 4 – 10
$299 per night
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Superhost
Cabin in Red Hook
Modern Upstate Cabin, near Rhinebeck NY
1 queen bed
Oct 31 – Nov 6
$350 per night
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Superhost
Cottage in Hudson
Private Pool + Newly Remodeled Cottage + Fire Pit
1 bed
Oct 16 – 21
$186 per night, originally $223
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Superhost
Cottage in East Chatham
Relaxing Retreat-Enjoy Hudson Valley & Berkshires
6 beds
Dec 30 – Jan 4
$237 per night
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Superhost
Apartment in Philmont
Beautiful space in the heart of Philmont
1 double bed
Oct 16 – 21
$150 per night
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Superhost
Tiny home in Chatham
Tiny House Amid the Grandeur of The Hudson Valley
2 queen beds
Nov 27 – Dec 2
$185 per night
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Home in Austerlitz
Chester by AvantStay | Amazing Views, Secluded Home, A True City Escape!
8 beds
Oct 23 – 28
$293 per night
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Superhost
Guest suite in Austerlitz
Rustic-Modern Studio - Near Hudson, Chatham, & GB
1 queen bed
Oct 23 – 30
$71 per night, originally $90
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Superhost
Home in Chatham
Secluded Post-and-Beam Chalet w/Breathtaking Views
4 beds
Oct 4 – 9
$265 per night
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Home in Canaan
Comfy - Country Family Home- Affordable
2 beds
Oct 9 – 14
$75 per night
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Superhost
Cabin in Old Chatham
RaW Magical Cabin in the Woods
2 beds
Nov 5 – 10
$199 per night
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Superhost
Tiny home in Chatham
The Honeydew: Tree house vibes w/private hot tub
2 queen beds
Oct 23 – 28
$233 per night
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Superhost
Home in Athens
Cozy 2 Bedroom New construction!
4 beds
Oct 2 – 9
$165 per night, originally $194
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Superhost
Private room in North Chatham
Arnold Farmhouse (Italianate - private bath)
1 double bed
Oct 9 – 14
$93 per night
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Superhost
Home in Kinderhook
Charming Kinderhook Village Victorian Duplex
2 beds
Nov 6 – 11
$101 per night