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

Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

Leslie's Retreat: Spacious home ideally located to everything

"Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Spacious 6 bedroom 4.5 bath house in charming Marblehead & close to the ocean

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

Hyannis Hideaway in Cape Cod

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
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 | 532 Holiday Homes |
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Lowest Price | AU$310 |
Highest Price | AU$2,122 |
Popular accommodation | Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach, Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi, Leslie's Retreat: Spacious home ideally located to everything, "Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester, Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC , Spacious 6 bedroom 4.5 bath house in charming Marblehead & close to the ocean, LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches, Hyannis Hideaway in Cape Cod, Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs |
Holiday Homes in Eastern Massachusetts
Top Locations for Holiday Homes in Eastern Massachusetts
More accommodations in Eastern Massachusetts
Top trending hotels in Eastern Massachusetts

Omni Boston Hotel at the Seaport

Hilton Boston Park Plaza

citizenM Boston North Station

citizenM Boston Back Bay
More ways to explore Eastern Massachusetts
Top picks
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^Subject to availability and chosen travel dates.