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

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is AU$368 per night from 4 Apr to 5 Apr
AU$368
includes taxes & fees
4 Apr - 5 Apr
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!!
Hancock Village Inn at Jiminy Peak

Hancock Village Inn at Jiminy Peak

Hancock
The price is AU$1,675 per night from 4 Apr to 5 Apr
AU$1,675
includes taxes & fees
4 Apr - 5 Apr
With a stay at this vacation home in Pittsfield, you'll be on the waterfront, within a 5-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.
Hancock Village Inn at Jiminy Peak
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.
Save an average of 15% on thousands of hotels when you're signed in
Lakeside Retreat Just You, The Lake & The View!

Lakeside Retreat Just You, The Lake & The View!

Great Barrington
Located in Great Barrington, this vacation home is on the waterfront, within a 10-minute drive of Art et Industrie and Housatonic River.
Lakeside Retreat Just You, The Lake & The View!
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$552 per night from 16 Apr to 17 Apr
AU$552
includes taxes & fees
16 Apr - 17 Apr
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 Retreat w/ Hot Tub, on Sleepy Hollow Lake!

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

Athens
With a stay at this vacation home in Athens, you'll be on the waterfront, just a 1-minute walk from Sleepy Hollow Lake and 13 minutes by foot from Hudson ...
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!
Secluded Lux Mansion Pool Home with Amazing Views

Secluded Lux Mansion Pool Home with Amazing Views

Nassau
Located in Nassau, this vacation home is on a lake, within a 10-minute drive of Brookview Station Winery and Berkshire Retreat Center.
Secluded Lux Mansion Pool Home with Amazing Views
Heart of Lenox Walk to Town Cozy Cottage!

Heart of Lenox Walk to Town Cozy Cottage!

Lenox
With a stay at this vacation home in Lenox, you'll be within a 5-minute drive of Tanglewood Music Center and The Bookstore.
Heart of Lenox Walk to Town Cozy Cottage!
Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

Coxsackie
When you a stay at this vacation home in Athens, you'll be on the beach, just steps from Hudson River and Hudson River Islands State Park.
Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi
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
539 Holiday Homes
Lowest Price
AU$157
Highest Price
AU$1,675
Popular accommodation
Berkshire Village Carriage House - Super Private!!, Hancock Village Inn at Jiminy Peak, Spectacular views and close to Great Barrington., Lakeside Retreat Just You, The Lake & The View!, COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!, Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!, Secluded Lux Mansion Pool Home with Amazing Views, Heart of Lenox Walk to Town Cozy Cottage!, Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

Top trending hotels in Chatham

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$173 per night from 16 Apr to 17 Apr
AU$173
includes taxes & fees
16 Apr - 17 Apr
With a stay at Life House Berkshires in Lenox, you'll be within a 10-minute drive of Tanglewood Music Center and Kennedy Park.
Life House Berkshires
Comfort Inn Glenmont - Albany South

Comfort Inn Glenmont - Albany South

2.5 out of 5
37 Route 9W, Glenmont, NY
Fully refundable
The price is AU$176 per night from 4 May to 5 May
AU$176
includes taxes & fees
4 May - 5 May
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
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$157 per night from 10 Apr to 11 Apr
AU$157
includes taxes & fees
10 Apr - 11 Apr
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
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is AU$225 per night from 13 Apr to 14 Apr
AU$225
includes taxes & fees
13 Apr - 14 Apr
With a stay at Vacation Village in the Berkshires in Williamstown, you'll be a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain ...
Vacation Village in the Berkshires
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.