Chatham Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Vacation Rentals in Chatham

Don't see what you're looking for?
See all available properties in Chatham
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chatham Vacation Rentals essential information

Accommodation
428 Vacation Rentals
Lowest Price
$220
Highest Price
$534
Popular accommodation
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con, COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!, Cozy Cape Close to Everything: Family, hiking, shopping and restaurants! , Amore Estate - beautiful room with many places to explore and relax in., Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!, Secluded Family Home in Serene Stockbridge Woods, Spectacular views and close to Great Barrington., Berkshire Village Carriage House - Super Private!!, Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool, Luxury Barn Retreat . Year-Round Paradise. OVER 100 5 STAR REVIEWS!!, Beautiful Lenox Home, 3 Mi to Shakespeare & Co!