Book Holiday Homes in Chatham

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Featured Holiday Homes in Chatham

Charming Home Close to Everything.  Discounts for the fall and winter

Charming Home Close to Everything. Discounts for the fall and winter

Eastham
Book a stay at this family-friendly vacation home in Eastham. Enjoy free WiFi, a garden, and patios. Popular attractions Cape Cod National Seashore and Poit's ...
Charming Home Close to Everything. Discounts for the fall and winter
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
Book a stay at this beach vacation home in Chatham. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Hardings Beach ...
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK
Idyllic Waterfront Home on Drummer Cove  in Quiet Pine Grove on Pleasant Point.

Idyllic Waterfront Home on Drummer Cove in Quiet Pine Grove on Pleasant Point.

Wellfleet
Book a stay at this family-friendly vacation home in Wellfleet. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Cape ...
Idyllic Waterfront Home on Drummer Cove in Quiet Pine Grove on Pleasant Point.
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Spacious cape house near Craigville Beach, downtown Centerville, Hyannis & more!

Spacious cape house near Craigville Beach, downtown Centerville, Hyannis & more!

Barnstable
Stay at this vacation home in Centerville. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Hyannis Harbor and Barnstable Performing ...
Spacious cape house near Craigville Beach, downtown Centerville, Hyannis & more!
Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK

Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK

Chatham
Book a stay at this family-friendly vacation home in Chatham. Enjoy private pools, patios, and cable/satellite TV service. Popular attractions Hardings Beach ...
Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Chatham
The price is NZ$714 per night from 26 Nov to 27 Nov
NZ$714
includes taxes & fees
26 Nov - 27 Nov
Stay at this vacation home in Chatham. Enjoy a water park, a garden, and patios. Popular attractions Hardings Beach and Ridgevale Beach are located nearby.
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Darling Cape Cottage - Steps from Downtown Harwich Port

Darling Cape Cottage - Steps from Downtown Harwich Port

Harwich
Stay at this vacation home in Harwich Port. Enjoy free WiFi, a garden, and patios. Popular attractions Bank Street Beach and Harwich Port are located ...
Darling Cape Cottage - Steps from Downtown Harwich Port
East Orleans - walk to Nauset Beach

East Orleans - walk to Nauset Beach

Orleans
Stay at this vacation home in Orleans. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Nauset Inlet and Stony Island are located ...
East Orleans - walk to Nauset Beach
Dream coastal dog-friendly vacation 4-bedroom home. Steps from Keyes Beach!

Dream coastal dog-friendly vacation 4-bedroom home. Steps from Keyes Beach!

Hyannis
Book a stay at this family-friendly vacation home in Hyannis. Enjoy free WiFi, a water park, and a garden. Popular attractions Hyannis Harbor and Keyes Memorial ...
Dream coastal dog-friendly vacation 4-bedroom home. Steps from Keyes Beach!
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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
2226 Holiday Homes
Lowest Price
NZ$135
Highest Price
NZ$714
Popular accommodation
Charming Home Close to Everything. Discounts for the fall and winter , Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK, Idyllic Waterfront Home on Drummer Cove in Quiet Pine Grove on Pleasant Point., Spacious cape house near Craigville Beach, downtown Centerville, Hyannis & more!, Walk 2Beach, Pool, Hot Tub, GameRoom, PetsOK, Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK, Darling Cape Cottage - Steps from Downtown Harwich Port, East Orleans - walk to Nauset Beach, Dream coastal dog-friendly vacation 4-bedroom home. Steps from Keyes Beach!

Top trending hotels in Chatham

Chatham Bars Inn

Chatham Bars Inn

5 out of 5
297 Shore Rd, Chatham, MA
The price is NZ$482 per night from 2 Dec to 3 Dec
NZ$482
includes taxes & fees
2 Dec - 3 Dec
Book a stay at this luxury resort in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
Chatham Bars Inn
Chatham Wayside Inn

Chatham Wayside Inn

4 out of 5
512 Main St, Chatham, MA
The price is NZ$459 per night from 4 Dec to 5 Dec
NZ$459
includes taxes & fees
4 Dec - 5 Dec
Stay at this 4-star golf hotel in Chatham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our ...
Chatham Wayside Inn
Chatham Seafarer Inn

Chatham Seafarer Inn

3.5 out of 5
2079 Main St, Chatham, MA
Stay at this 3.5-star hotel in Chatham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Cockle Cove Beach and Ridgevale Beach are located ...
Chatham Seafarer Inn
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Cape Sands Inn

Cape Sands Inn

2.5 out of 5
149 Main St - RT 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
The price is NZ$135 per night from 26 Nov to 27 Nov
NZ$135
includes taxes & fees
26 Nov - 27 Nov
Book a stay at this family-friendly motel in West Yarmouth. Enjoy free parking, an outdoor pool, and a sauna. Our guests praise the pool and the helpful staff ...
Cape Sands Inn
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See all available properties in Chatham
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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.

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^Subject to availability and chosen travel dates.