300+ stays

Stays in Chatham

Review COVID-19 travel restrictions before you book.
Learn more
SUPERHOST
Entire house in Egremont
Premier Waterfront Home!
8 guests2 bedrooms3 beds2 baths
WifiAir conditioningKitchenPets allowed
$283 per night
Entire house in Hillsdale
Eclectic Columbia County Home
9 guests4 bedrooms5 beds3.5 baths
WifiAir conditioningKitchenFree parking
$250 per night
SUPERHOST
Entire house in Hillsdale
Breezy Hill: Massive Views, 1 mile to Catamount Ski!!
9 guests4 bedrooms6 beds2 baths
WifiAir conditioningKitchenPets allowed
$184 per night
Entire house in East Chatham
Windswept Acres In the Berkshires~Canaan, New York
4 guests3 bedrooms3 beds1 bath
WifiAir conditioningKitchenFree parking
$214 per night
SUPERHOST
Entire cottage in Old Chatham
Berkshires / Hudson Loft
4 guestsStudio2 beds1 bath
WifiAir conditioningKitchenFree parking
$156 per night
Entire house in Chatham
Beautiful Hudson Valley Views
6 guests2 bedrooms2 beds2 baths
WifiKitchenFree parkingIndoor fireplace
$325 per night
Entire cottage in Great Barrington
Artist Cottage at the Foot of Monument Mountain
2 guests1 bedroom1 bed2 baths
WifiAir conditioningKitchenFree parking
$204 per night
Entire house in Old Chatham
The Red Barn
8 guests3 bedrooms5 beds3.5 baths
WifiAir conditioningKitchenFree parking
$350 per night
SUPERHOST
Entire guest suite in Chatham
The Inn at Chatham - Romantic getaway
3 guests1 bedroom1 bed1 bath
WifiAir conditioningFree parkingSelf check-in
$95 per night
SUPERHOST
Entire house in Hudson
Rushing Rapids Cottage – a birdwatcher's paradise
5 guests2 bedrooms3 beds2 baths
WifiAir conditioningKitchenFree parking
$125 per night
SUPERHOST
Entire guesthouse in Canaan
Airy cottage with meadow views in The Berkshires
4 guests1 bedroom3 beds1 bath
WifiKitchenFree parkingPets allowed
$145 per night
Entire cottage in Hudson
Charming Peppercorn Cottage - Hudson, NY
4 guests2 bedrooms2 beds1 bath
WifiAir conditioningKitchenFree parking
$131 per night
SUPERHOST
Entire house in Old Chatham
Secluded House in Historic Old Chatham, NY
8 guests3 bedrooms5 beds2.5 baths
WifiAir conditioningKitchenFree parking
$195 per night
SUPERHOST
Private room in Valatie
Charming Eyebrow Colonial North Chatham, NY
2 guests1 bedroom1 bed1 private bath
WifiAir conditioningKitchenFree parking
$95 per night
SUPERHOST
Entire cottage in Craryville
Raspberry Ridge Cottage
6 guests3 bedrooms4 beds2 baths
Air conditioningKitchenFree parkingPets allowed
$142 per night
SUPERHOST
Farm stay in Ghent
Retrograss Farm Apartment
6 guests2 bedrooms3 beds1 bath
WifiAir conditioningKitchenFree parking
$125 per night
SUPERHOST
Entire house in Ghent
Blacksmith House, Ghent, NY
4 guests3 bedrooms2 beds2 baths
WifiAir conditioningKitchenFree parking
$200 per night
SUPERHOST
Entire loft in Hudson
The Mechanic's Studio · Hudson NY
2 guestsStudio1 bed1 bath
WifiAir conditioningKitchenPets allowed
$88 per night
SUPERHOST
Entire house in Canaan
Sunny Treetop Chalet with Mountain Views
6 guests3 bedrooms3 beds2 baths
WifiKitchenFree parkingIndoor fireplace
$170 per night
SUPERHOST
Private room in Old Chatham
Haddock Hill House
2 guests1 bedroom1 bed1 private bath
WifiAir conditioningFree parking
$144 per night
2345…15
1 – 20 of 300+ places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.