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

Spacious 5-bedroom 5 bath house in charming Marblehead & close to the ocean

Ocean Edge Condo with Guest Passes to Pool, Golf, and Sports available!

"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

Bright Boston House | near T

Clean, Contemporary Escape | Near T

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

Cape Cod Getaway – 3BR Sandwich Home, Walk to Beach, AC & WiFi

Best location in Old Town home, 5 minutes to everything, enjoy the difference!

Hyannis Hideaway in Cape Cod
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 | 489 Holiday Homes |
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Popular accommodation | Spacious 5-bedroom 5 bath house in charming Marblehead & close to the ocean, Ocean Edge Condo with Guest Passes to Pool, Golf, and Sports available!, "Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester, Bright Boston House | near T, Clean, Contemporary Escape | Near T, Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!, Cape Cod Getaway – 3BR Sandwich Home, Walk to Beach, AC & WiFi, Best location in Old Town home, 5 minutes to everything, enjoy the difference!, Hyannis Hideaway in Cape Cod |
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 Back Bay

Copley Square Hotel, a FOUND Hotel

Harborside Inn Of Boston
More ways to explore Eastern Massachusetts
Top picks
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^Subject to availability and chosen travel dates.