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Vacation rentals in Chatham

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Top-rated vacation rentals in Chatham

Guests agree: these stays are highly rated for location, cleanliness, and more.

Tiny home in Chatham
HoneyHouse: The Perfect Couple's Retreat
This one-of-a-kind thoughtfully curated space is the perfect getaway—2.5 hours from NYC or Boston (just off the Taconic). You'll fall in love with this PRIVATE oasis in a canopy of trees overlooking the creek. Star gaze from your private hot tub (open year-round), sip cocktails around the fire. Steps from restaurants, brewery, shops, theater, galleries. Cook in the well-equipped kitchen/outdoor grill OR walk to dinner. Immerse yourself in nature while enjoying the convenience of village life.
$214 per night
Tiny home in Chatham
Tiny House Amid the Grandeur of The Hudson Valley
Welcome to "The Tiny" at The Hemptons in Upstate New York! The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Although we'd encourage you to check out many the local eateries (see below)! The bathroom is full size and likely bigger than the one in your first NYC apartment.
$181 per night
Private room in Chatham
The Inn at Chatham - Romantic getaway
Beautiful , private 1-bedroom suite in a gracious 1820s Chatham home in the center of Chatham Village, right off of the Main Street- the perfect getaway! Your own entrance to a federal-inspired living space and a huge Edwardian bedroom with high ceilings and large windows. Easy walking to Village shops, cinema, brewery and restaurants - close to Hudson and Berkshires, hiking, skiing, museums, Tanglewood, etc. Get away from it all while being close to amenities.
$95 per night

Stay near Chatham's top sights

Photo of Chatham Grill
Chatham Grill21 locals recommend
Photo of Chatham Brewing
Chatham Brewing114 locals recommend
Photo of Our Daily Bread Deli
Our Daily Bread Deli66 locals recommend
Photo of Columbia County Fair Grounds
Columbia County Fair Grounds7 locals recommend
Photo of Yianni's
Yianni's20 locals recommend
Photo of The People's Pub
The People's Pub56 locals recommend

Other great vacation rentals in Chatham

Home in Chatham
2BR Chatham Vlg Home Wi-fi Park@Door Keyless 55"TV
$98 per night
Home in Kinderhook
Charming Kinderhook Village Victorian Duplex
$130 per night
Home in Chatham
Pet-friendly, Chatham, NY. No neighbors in sight.
$126 per night
Barn in Kinderhook
Unique Village Antique Print/Shop Studio Apartment
$109 per night
Guest suite in Valatie
Guest Suite in Old Chatham Hunt Country
$105 per night
Rental unit in Canaan
Mountain View Getaway
$93 per night
Cottage in Kinderhook
The Cottage on Sylvester Street
$131 per night
Cottage in Old Chatham
Berkshires / Hudson Loft
$174 per night
Home in Old Chatham
Charming Country Cottage w/ Private Garden Gazebo
$205 per night
Home in Chatham
Hilltop studio apartment on 100 acres near village
$120 per night
Guest suite in Austerlitz
Rustic-Modern Studio - Near Hudson, Chatham, & GB
$75 per night
Rental unit in Chatham
Cute Modern Victorian Suite in the village
$120 per night
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