Currently showing Any week, Add guests. Change search.

Over 1,000 places

Superhost
Home in Chatham
Pet-friendly, Chatham, NY. No neighbors in sight.
3 beds
Oct 22 – 27
$160 per night
Superhost
Cottage in Craryville
Columbia County Getaway - Raspberry Ridge Cottage
4 beds
Oct 1 – 6
$120 per night
Superhost
Apartment in Canaan
Queechy Lake Carriage House
2 beds
Oct 1 – 6
$68 per night
Apartment in Philmont
New Karelia, Apartment close to Hudson
3 beds
Oct 22 – 27
$125 per night
Superhost
Home in Craryville
Lakeside Artist’s Cottage near Waterfalls & Hiking
3 beds
Oct 2 – 7
$130 per night, originally $181
Apartment in East Chatham
Bennett Abode
1 double bed
Oct 1 – 6
$86 per night
Guesthouse in Great Barrington
Sweet Victorian in Housatonic
5 beds
Oct 1 – 6
$135 per night
Home in Craryville
Hudson Valley Swim/Ski Lake House Rental
4 beds
Oct 8 – 13
$196 per night
Home in Copake
Copake Cottage
2 beds
Oct 8 – 13
$160 per night, originally $200
Superhost
Cottage in Craryville
The Craryville Cottage
2 beds
Oct 1 – 6
$195 per night
Barn in Craryville
Barn Home & Chicken Farm
4 beds
Oct 2 – 7
$256 per night, originally $300
Superhost
Home in Copake
Yellow Door House
2 double beds
Oct 23 – 28
$111 per night
Superhost
Cabin in Copake Lake
Secluded Cabin w/ PRIVATE HOT TUB and LAKE ACCESS
2 beds
Oct 28 – Nov 2
$170 per night
Superhost
Cottage in Kinderhook
Spacious Cottage Retreat on Beautiful 2-Acres
2 beds
Oct 19 – 24
$147 per night
Superhost
Condo in Hudson
Harmony Valley Home, bright & inviting 2-BR escape
2 queen beds
Oct 22 – 27
$88 per night, originally $110
Superhost
Cottage in Hillsdale
Cozy Cottage between Hudson & Berkshires
1 double bed
Oct 1 – 6
$99 per night
Superhost
Cottage in Austerlitz
Cozy Berkshire Cottage
6 beds
Oct 1 – 6
$250 per night
Superhost
Home in Craryville
Cheerful two bedroom home in Craryville
3 beds
Oct 1 – 6
$180 per night