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.

Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 250 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!

Sep 14 – 21

€ 122 per night
Guest favorite

Home in Ghent

4.87 out of 5 average rating, 264 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

Escape to our recently renovated guest house on a 12-acre property, 15min from of Hudson. Cozy up in front of the wood burning stove as you take in the rural setting through oversized glass doors. Infared Sauna is within running distance of the swimming pond for a cold plunge. Located in a park like setting of rolling hills & colorful sugar maple trees. Fully equipped kitchen, memory foam mattress and all the amenities. In home Massage/Yoga available. XC ski from the house! 45min to downhill.

Oct 12 – 19

€ 289 per night
Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 178 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)! The bathroom is full size and likely bigger than the one in your first NYC apartment.

Sep 13 – 20

€ 152 per night

Popular amenities for Chatham vacation rentals

Stay near Chatham's top sights

Our Daily Bread Deli66 locals recommend
Chatham Brewing114 locals recommend
Chatham Grill21 locals recommend
Columbia County Fair Grounds7 locals recommend
Yianni's20 locals recommend
The People's Pub54 locals recommend

Other great vacation rentals in Chatham

Guest favorite

Apartment in Valatie

4.94 out of 5 average rating, 164 reviews

Holland House: Modern Rustic Guest Apartment

Feb 10 – 17

€ 152 per night
Guest favorite

Cabin in Ghent

4.99 out of 5 average rating, 176 reviews

Cozy chalet w/ fireplace near Hudson & hiking

Aug 3 – 10

€ 369 per night
Guest favorite

Home in Ghent

4.98 out of 5 average rating, 104 reviews

Stylish Hawthorne Valley Farmhouse Retreat

Mar 4 – 11

€ 349 per night
Guest favorite

Tiny home in Ghent

4.96 out of 5 average rating, 139 reviews

Country Getaway Tiny House in woods w/Pool/Sauna

Apr 9 – 16

€ 298 per night
Guest favorite

Home in Ghent

4.94 out of 5 average rating, 121 reviews

Blacksmith House, Ghent, NY

Aug 27 – Sep 3

€ 229 per night
Guest favorite

Home in Chatham

4.98 out of 5 average rating, 96 reviews

Hilltop studio apartment on 100 acres near village

Apr 7 – 14

€ 114 per night
Guest favorite

Apartment in Chatham

4.91 out of 5 average rating, 34 reviews

Neat 2 bedroom in the village private access

Jun 16 – 23

€ 136 per night
Guest favorite

Apartment in Canaan

5.0 out of 5 average rating, 81 reviews

Mountain View Getaway

Nov 18 – 25

€ 107 per night
Guest favorite

Home in Old Chatham

5.0 out of 5 average rating, 18 reviews

The Red House

Nov 5 – 12

€ 180 per night
Guest favorite

Home in Chatham

5.0 out of 5 average rating, 17 reviews

Chatham Cozy Bright Country Getaway

Jan 28 – Feb 4

€ 166 per night
Guest favorite

Chalet in North Chatham

4.95 out of 5 average rating, 20 reviews

The Chalet on The Hill

May 28 – Jun 4

€ 359 per night
Guest favorite

Apartment in Valatie

4.98 out of 5 average rating, 43 reviews

Apartment w/Hudson-Electric Trail Access

Jan 21 – 28

€ 143 per night

Quick stats about vacation rentals in Chatham

Total rentals

10 properties

Local attractions

Our Daily Bread Deli, Chatham Brewing, and Chatham Grill

Popular amenities

Kitchen, Wifi, and Pool

Wifi availability

10 properties include access to wifi

Total number of reviews

910 reviews

Nightly prices starting at

€ 92 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Columbia County
  5. Chatham