Book Holiday Homes in Eastern Massachusetts
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Featured Holiday Homes in Eastern Massachusetts

Casa Castor • Private Room 1

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Leslie's Retreat: Spacious home ideally located to everything

Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston

Cozy Pet-Friendly 4BR | Fireplace, Patio and BBQ

Brand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Eastern Massachusetts 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 Eastern Massachusetts vacation homes are the perfect way for you to wing it.
Holiday houses in Eastern Massachusetts 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 Eastern Massachusetts 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 Eastern Massachusetts adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Eastern Massachusetts 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 Eastern Massachusetts 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.
Eastern Massachusetts Holiday Homes essential information
Accommodation | 505 Holiday Homes |
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Lowest Price | AU$252 |
Highest Price | AU$537 |
Popular accommodation | Casa Castor • Private Room 1, Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!, Leslie's Retreat: Spacious home ideally located to everything, Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!, LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches, Historic Brownstone Townhouse, 7 beds/3.5 baths, Fenway Boston, Cozy Pet-Friendly 4BR | Fireplace, Patio and BBQ, Brand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12, Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC |
Top trending hotels in Eastern Massachusetts

Seaport Hotel Boston

Omni Boston Hotel at the Seaport

citizenM Boston North Station

The Dagny Boston
More ways to explore Eastern Massachusetts
Top picks
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^Subject to availability and chosen travel dates.