Book Holiday Homes in Chatham

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Chatham

Gorgeous 3BR 3BA Sleeps 10  Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Hancock
The price is AU$839 per night from 18 Nov to 19 Nov
AU$839
includes taxes & fees
18 Nov - 19 Nov
With a stay at this vacation home, you'll be centrally located in Hancock, within a 5-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.
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 LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Craryville
The price is AU$577 per night from 18 Nov to 19 Nov
AU$577
includes taxes & fees
18 Nov - 19 Nov
With a stay at this vacation home in Copake Lake, you'll be within a 5-minute drive of Copake Lake and Mosquito Island.
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!

Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!

Rensselaer
Located in Rensselaer, this vacation home is in a rural location, a 5-minute drive from Hudson River and 6 minutes from Palace Theater.
Cozy Cape Close to Everything: Family, hiking, shopping and restaurants!
Save an average of 15% on thousands of hotels when you're signed in
Amore Estate -  beautiful room with many places to explore and relax in.

Amore Estate - beautiful room with many places to explore and relax in.

Lenox
With a stay at this vacation home in Lenox, you'll be within a 5-minute drive of Wyndhurst Golf & Club and Berkshire Scenic Railway Museum.
Amore Estate - beautiful room with many places to explore and relax in.
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Valatie
The price is AU$802 per night from 18 Nov to 19 Nov
AU$802
includes taxes & fees
18 Nov - 19 Nov
Located in Valatie, this vacation home is on the waterfront, a 1-minute drive from Kinderhook Lake and 6 minutes from Valatie Family Care.
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods

Stockbridge
Located in South Lee, this vacation home is in a rural location, within a 5-minute drive of Berkshire Botanical Garden and Housatonic River.
Secluded Family Home in Serene Stockbridge Woods
Spectacular views and close to Great Barrington.

Spectacular views and close to Great Barrington.

Great Barrington
Located in Great Barrington, this vacation home is within a 5-minute drive of Housatonic River and Housatonic River Walk.
Spectacular views and close to Great Barrington.
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is AU$320 per night from 18 Nov to 19 Nov
AU$320
includes taxes & fees
18 Nov - 19 Nov
Located in Lanesborough, this vacation home is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.
Berkshire Village Carriage House - Super Private!!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Stockbridge
With a stay at this vacation home in West Stockbridge, you'll be within a 5-minute drive of Berkshire Botanical Garden and Tanglewood Music Center.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
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 Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chatham vacation homes are the perfect way for you to wing it.

Holiday houses in Chatham let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chatham in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chatham adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chatham with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chatham vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chatham Holiday Homes essential information

Accommodation
428 Holiday Homes
Lowest Price
AU$161
Highest Price
AU$839
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

Top trending hotels in Chatham

Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

2.5 out of 5
37 Route 9W, Glenmont, NY
Fully refundableReserve now, pay when you stay
The price is AU$161 per night from 1 Dec to 2 Dec
AU$161
includes taxes & fees
1 Dec - 2 Dec
A stay at Comfort Inn Glenmont - Albany South places you in the heart of Glenmont, within a 10-minute drive of MVP Arena and Albany Capital Center.
Comfort Inn Glenmont - Albany South
Life House Berkshires

Life House Berkshires

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$168 per night from 18 Nov to 19 Nov
AU$168
includes taxes & fees
18 Nov - 19 Nov
Located in Lenox, Life House Berkshires is within a 15-minute walk of Kennedy Park and Pleasant Valley Wilderness Sanctuary.
Life House Berkshires
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AU$167 per night from 24 Nov to 25 Nov
AU$167
includes taxes & fees
24 Nov - 25 Nov
Located in Lenox, The Yankee, Trademark Collection by Wyndham is on the Strip, a 4-minute drive from Bousquet Ski Area and 7 minutes from Shakespeare and ...
The Yankee, Trademark Collection by Wyndham
Save an average of 15% on thousands of hotels when you're signed in
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street, Stockbridge, MA
Fully refundableReserve now, pay when you stay
The price is AU$297 per night from 25 Nov to 26 Nov
AU$297
includes taxes & fees
25 Nov - 26 Nov
When you a stay at The Red Lion Inn in Stockbridge, you'll be in the historical district, within a 5-minute walk of Housatonic River and Mission House.
The Red Lion Inn
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.