Chatham vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Chatham

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Home in Chatham

4.89 out of 5 average rating, 156 reviews

Chatham Village Fully Stocked Home 100% Smoke Free

WELCOME ALL. Pedestrian/Bike friendly Village home sits 200' to police station & Main St pubs/pizza/movies/fine dining hopping 12mi Hudson Amtrak (taxi, Uber avail). Town park w/swim pond & tennis courts half-mile. Tanglewood 24mi. Keyless entry. Host on premises always available. 100% smoke/pet-free property. Check-in 4pm/-out 11a. 55" Sony TV. Free high-speed WiFi. Fully stocked home. Private outdoor dining w/propane bbq. 2 guests max for ultimate comfort. Park @ door. See more details within

Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 196 reviews

Tiny House on 70 Private Acres in 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)! Bathroom is full size. We are located 10 min to Chatham, 25 min to Hudson & Tanglewood.

Guest favorite

Cabin in Ghent

5 out of 5 average rating, 200 reviews

Cozy chalet w/ fireplace near Hudson & hiking

3-bedroom, 2-bathroom home on 4 acres on a quiet street in charming Ghent, NY. Renovated in late 2021, this lovely chalet features 5-beds, open floor plan, luxury bathrooms, all-new, high-end appliances and cookware, a wood-burning fireplace, outdoor deck, and fire pits. The home is surrounded by nature—trees, trails, streams, and farms—all close by. Hike, bike, kayak, or go to a brewery. Discover the nearby Hudson Valley farms, ski in the Berkshires, or visit the trendy town of Hudson, NY.

Guest favorite

Rental unit in Copake Falls

4.93 out of 5 average rating, 272 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Guest favorite

Cottage in Kinderhook

4.98 out of 5 average rating, 188 reviews

The Cottage on Sylvester Street

The Cottage on Sylvester Street welcomes guests looking for a relaxing weekend or longer stay in a small-village setting. Located at the heart of the historic Village of Kinderhook, this stylishly renovated house is located amongst Kinderhook's collection of historic architectural gems. Within easy walking distance are eateries, wine and beer bars, The School I Jack Shainman Gallery, historic sites, the farmers' market plus farm stands, and quiet, scenic roads perfect for walking and cycling.

Guest favorite

Rental unit in Canaan

5 out of 5 average rating, 110 reviews

Mountain View Getaway

Come relax & enjoy panoramic mountain and pond views. Marvel at the dramatic lighting effects on Mercer Mt from sunrise-sunset from your private deck or bright living room. Fully equipped kitchen, grill on the deck, short scenic drive to a wide variety of restaurants & endless cultural venues in the surrounding quaint villages of Berkshire County Mass and Columbia County NY. Near hiking trails, skiing, apple picking & farm stores. Queechy Lake swimming, NYS boat launch for car top boats.

Guest favorite

Guest suite in Valatie

4.98 out of 5 average rating, 237 reviews

Guest Suite in Old Chatham Hunt Country

Looking for all the perks of a hotel while staying at a house in the country? This tranquil, light filled room overlooks horse pastures and a dirt road in the heart of Old Chatham hunt country. A private entrance leads to a guest suite which includes a queen size bed, sitting area, kitchenette, and walk-in closet. Located on the first floor of a newly built, net-zero home. Power comes from solar and solar water panels provide for guilt-free hot showers! 50 MBPS fiber optic Internet!

Guest favorite

Cottage in New Lebanon

4.95 out of 5 average rating, 182 reviews

The Writer's Cottage

The Writer's Cottage is a tiny white house on a country road; vintage, complete, and inspiring. Built in the nineteenth century, it's perfect for a solo traveler or a pair of travelers exploring the Berkshires and the Hudson Valley. If you like rustic buildings, you'll be a fan of the cottage; it's an incredibly cozy time warp. Queen bed and living quarters downstairs; airy loft up a narrow set of enclosed stairs. There's an orchard and lawn with grill, hammock and table.

Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 178 reviews

BLUSH: Boutique TINY home*private spa*walk to town

Cozy in at this Romantic-Private-Peaceful OASIS & just steps from quintessential Main St. Indulgences abound in this one-of-a-kind curated space w/ lounge in upstairs loft & PLUSH queen bed tucked in its own nook. A perfect getaway for 2. Fully equipped kitchen. Enjoy the convenience of village life with restaurants, brewery, shops, theater. Hike, explore town, soak in your PRIVATE HOT TUB, make s'mores at the firepit, or tuck in & cozy. @artparkhomes

Guest favorite

Farm stay in Pittsfield

4.99 out of 5 average rating, 131 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or take a walk on our hiking trail.

Guest favorite

Rental unit in Valatie

4.94 out of 5 average rating, 171 reviews

Holland House: Modern Rustic Guest Apartment

Thoughtfully designed two-bedroom apartment located above a former millinery shop built in 1880. Beautiful natural light. Mix of vintage and modern amenities, including two guest bedrooms, full kitchen and bath, high speed wifi, in-unit laundry and work desks. Private tree-shaded back porch overlooking Kinderhook Creek and Pachaquack Preserve. 20 minutes to Hudson. 30 minutes to Albany, the Berkshires and the Catskills.

Guest favorite

Cabin in Chatham

4.98 out of 5 average rating, 107 reviews

The Upstate Cabin: A secluded getaway in the woods

Cozy cabin tucked away in the woods, 2.5 hours north of NYC and 2.5 hours west of Boston - where the Catskills meet the Berkshires. There's hiking in the summer, skiing in the winter, and total peace & quiet year-round. This entire cabin has been hand-lovingly restored and we can't wait to share the space with you. Follow us on Insta at @theupstatecabin to follow our upstate adventures and cabin transformation.

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chatham vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Chatham's top sights

Columbia County Fair Grounds7 locals recommend

Chatham Brewing114 locals recommend

Our Daily Bread Deli66 locals recommend

Chatham Grill21 locals recommend

Yianni's20 locals recommend

The People's Pub54 locals recommend

House rentals in Chatham

Guest favorite

Home in Ghent

4.98 out of 5 average rating, 112 reviews

Stylish Hawthorne Valley Farmhouse Retreat

Guest favorite

Home in Catskill

4.99 out of 5 average rating, 146 reviews

Athens, NY House - 1 Bedroom "Want to Get Away"?

Guest favorite

Home in Ghent

4.9 out of 5 average rating, 266 reviews

Renovated guesthouse on 52 acres!

Guest favorite