Vacation rentals in Chatham

Find and book unique accommodations on Airbnb

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

SUPERHOST

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

SUPERHOST

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

SUPERHOST