Book Holiday Homes in Chatham

Start date: Check-in selected.
To Date
End date: Check-out

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

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Dennis MA
The price is AU$475 per night from 28 Dec to 29 Dec
AU$475
28 Dec - 29 Dec
includes taxes & fees
When you stay at this vacation home in Dennis Port, you'll be by the sea, within a 5-minute drive of Cape Cod Theatre Company – Home of the Harwich Jr. Theatre ...
Opens in a new window2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Lovely Dog Friendly Beach Home Close to Everything. Jan-April monthly discounts

Lovely Dog Friendly Beach Home Close to Everything. Jan-April monthly discounts

Eastham MA
When you stay at this vacation home in Eastham, you'll be by the sea, within a 5-minute drive of Poit's Lighthouse Mini Golf and Arnold's Mini Golf.
Opens in a new windowLovely Dog Friendly Beach Home Close to Everything. Jan-April monthly discounts
Completely Renovated Cottage Overlooking Nantucket Sound with Private Beach

Completely Renovated Cottage Overlooking Nantucket Sound with Private Beach

Dennis MA
With a stay at this vacation home in Dennis Port, you'll be on the beach, just a 1-minute walk from Cape Cod Beaches and 6 minutes by foot from Sea Street ...
Opens in a new windowCompletely Renovated Cottage Overlooking Nantucket Sound with Private Beach
Save an average of 15% on thousands of hotels when you're signed in
WATERFRONT Kayaks & SUP’s ★ Pet friendly ★ HOT TUB ★ Firepit & FPL★ King bed

WATERFRONT Kayaks & SUP’s ★ Pet friendly ★ HOT TUB ★ Firepit & FPL★ King bed

Yarmouth MA
With a stay at this vacation home in South Yarmouth (Bass River), you'll be within a 5-minute drive of Bass River Sports World and Cultural Center of Cape ...
Opens in a new windowWATERFRONT Kayaks & SUP’s ★ Pet friendly ★ HOT TUB ★ Firepit & FPL★ King bed
Comfy Cape Home: Close to Mayflower Beach, golf course, and Downtown

Comfy Cape Home: Close to Mayflower Beach, golf course, and Downtown

Dennis MA
The price is AU$1,094 per night from 17 Dec to 18 Dec
AU$1,094
17 Dec - 18 Dec
includes taxes & fees
With a stay at this vacation home in Dennis, you'll be within a 5-minute drive of Follins Pond and Scargo Hill Observation Tower.
Opens in a new windowComfy Cape Home: Close to Mayflower Beach, golf course, and Downtown
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Chatham MA
Located in Chatham, this vacation home is by the sea, within a 5-minute drive of Hardings Beach and Cape Cod Beaches.
Opens in a new windowBreathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Chatham MA
The price is AU$746 per night from 15 Dec to 16 Dec
AU$746
15 Dec - 16 Dec
includes taxes & fees
A stay at this vacation home places you in the heart of Chatham, within a 5-minute walk of Chatham Windmill and Mayo House.
Opens in a new windowQuaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Wellfleet MA
The price is AU$662 per night from 15 Dec to 16 Dec
AU$662
15 Dec - 16 Dec
includes taxes & fees
With a stay at this vacation home in South Wellfleet, you'll be on the beach, just a 1-minute walk from Lieutenant Island and 11 minutes by foot from South Lieutenant ...
Opens in a new windowSpectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
Watch the Sunset from this Bayfront Home! (1349)

Watch the Sunset from this Bayfront Home! (1349)

Wellfleet MA
With a stay at this vacation home in Wellfleet, you'll be on the beach, just a 1-minute walk from Cape Cod Beaches and 10 minutes by foot from Ryder Beach.
Opens in a new windowWatch the Sunset from this Bayfront Home! (1349)
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
2470 Holiday Homes
Lowest Price
AU$470
Highest Price
AU$1,094
Popular accommodation
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Lovely Dog Friendly Beach Home Close to Everything. Jan-April monthly discounts, Completely Renovated Cottage Overlooking Nantucket Sound with Private Beach, WATERFRONT Kayaks & SUP’s ★ Pet friendly ★ HOT TUB ★ Firepit & FPL★ King bed, Comfy Cape Home: Close to Mayflower Beach, golf course, and Downtown , Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK, Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches, Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly, Watch the Sunset from this Bayfront Home! (1349)

Top trending hotels in Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd Chatham MA
The price is AU$470 per night from 17 Dec to 18 Dec
AU$470
17 Dec - 18 Dec
includes taxes & fees
When you a stay at Chatham Bars Inn in Chatham, you'll be on the boardwalk/promenade, within a 5-minute walk of Chatham Seaside Links and Cape Cod Beaches.
Opens in a new windowChatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St Chatham MA
Fully refundableReserve now, pay when you stay
When you a stay at Chatham Wayside Inn in Chatham, you'll be next to a golf course, just steps from Mayo House and Gallery Antonia.
Opens in a new windowChatham Wayside Inn
Surfside Inn Chatham

Surfside Inn Chatham

2.5 out of 5
25 Holway St Chatham MA
When you a stay at Surfside Inn Chatham in Chatham, you'll be on the waterfront, within a 5-minute walk of Chatham Lighthouse Beach and Cape Cod Beaches.
Opens in a new windowSurfside Inn Chatham
Save an average of 15% on thousands of hotels when you're signed in
The Hawthorne

The Hawthorne

2 out of 5
196 Shore Rd Chatham MA
With a stay at The Hawthorne in Chatham, you'll be on the beach, just a 3-minute walk from Cape Cod Beaches and 5 minutes by foot from Chatham Seaside ...
Opens in a new windowThe Hawthorne
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.