Book Holiday Homes in Eastern Massachusetts

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Featured Holiday Homes in Eastern Massachusetts

Ocean Dreams, Waves as far as the eyes can see...........

Ocean Dreams, Waves as far as the eyes can see...........

Scituate MA
The price is AU$1,492 per night from 3 Jan to 4 Jan
AU$1,492
3 Jan - 4 Jan 2026
includes taxes & fees
With a stay at this vacation home in Scituate, you'll be on the beach, just a 2-minute walk from Scituate Lighthouse and 6 minutes by foot from Sand Hills ...
Opens in a new windowOcean Dreams, Waves as far as the eyes can see...........
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino

Chelsea MA
The price is AU$820 per night from 5 Jan to 6 Jan
AU$820
5 Jan - 6 Jan 2026
includes taxes & fees
When you stay at this vacation home in Chelsea, you'll be on the waterfront, within a 10-minute drive of Encore Boston Harbor and TD Garden.
Opens in a new windowWaterfront House Minutes from the Boston Downtown, Airport, Encore Casino
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

Falmouth MA
A stay at this vacation home places you in the heart of Falmouth, within a 15-minute walk of Cape Cod Beaches and Main Street.
Opens in a new windowFalmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
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Beautiful 5BR with Pool. 3 Renovated Levels of Luxury. Walk to Town or Beach.

Beautiful 5BR with Pool. 3 Renovated Levels of Luxury. Walk to Town or Beach.

Nantucket MA
Located in Nantucket, this vacation home is within a 5-minute drive of Founder's Cemetery and Old Gaol.
Opens in a new windowBeautiful 5BR with Pool. 3 Renovated Levels of Luxury. Walk to Town or Beach.
Charming private townhouse-style lodging, a block from Marblehead Harbor

Charming private townhouse-style lodging, a block from Marblehead Harbor

Marblehead MA
A stay at this vacation home places you in the heart of Marblehead, within a 5-minute drive of Marblehead Museum & Historical Society and Massachusetts Bay.
Opens in a new windowCharming private townhouse-style lodging, a block from Marblehead Harbor
Beautifully Renovated Cozy Home

Beautifully Renovated Cozy Home

Medford MA
With a stay at this vacation home in Medford, you'll be a 4-minute drive from Tufts University and 9 minutes from Encore Boston Harbor.
Opens in a new windowBeautifully Renovated Cozy Home
Leslie's Retreat: Spacious home ideally located to everything

Leslie's Retreat: Spacious home ideally located to everything

Salem MA
A stay at this vacation home places you in the heart of Salem, within a 15-minute walk of Witch House and Witch Dungeon Museum.
Opens in a new windowLeslie's Retreat: Spacious home ideally located to everything
Spacious, New Renovation | Near T

Spacious, New Renovation | Near T

Boston MA
With a stay at this vacation home in Boston (Dorchester), you'll be a 4-minute drive from Northeastern University and 6 minutes from Copley Square.
Opens in a new windowSpacious, New Renovation | Near T
Hidden Gem right in the city of Boston!

Hidden Gem right in the city of Boston!

Boston MA
The price is AU$492 per night from 6 Jan to 7 Jan
AU$492
6 Jan - 7 Jan 2026
includes taxes & fees
With a stay at this vacation home in Boston (Hyde Park), you'll be within a 15-minute drive of Fenway Park and Copley Square.
Opens in a new windowHidden Gem right in the city of Boston!
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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.

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
447 Holiday Homes
Lowest Price
AU$290
Highest Price
AU$1,492
Popular accommodation
Ocean Dreams, Waves as far as the eyes can see..........., Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino, Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown, Beautiful 5BR with Pool. 3 Renovated Levels of Luxury. Walk to Town or Beach., Charming private townhouse-style lodging, a block from Marblehead Harbor, Beautifully Renovated Cozy Home, Leslie's Retreat: Spacious home ideally located to everything, Spacious, New Renovation | Near T, Hidden Gem right in the city of Boston!

Top trending hotels in Eastern Massachusetts

Hilton Boston Back Bay

Hilton Boston Back Bay

4 out of 5
40 Dalton St Boston MA
Fully refundableReserve now, pay when you stay
The price is AU$290 per night from 4 Jan to 5 Jan
AU$290
4 Jan - 5 Jan 2026
includes taxes & fees
With a stay at Hilton Boston Back Bay, you'll be centrally located in Boston, steps from The Shops at Prudential Center and within a 5-minute walk of Berklee ...
Opens in a new windowHilton Boston Back Bay
Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
Harborside Inn Of Boston is in the heart of Boston, within a 5-minute walk of Faneuil Hall Marketplace and Quincy Market.
Opens in a new windowHarborside Inn Of Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

5 out of 5
450 Summer Street Boston MA
Fully refundableReserve now, pay when you stay
The price is AU$309 per night from 1 Jan to 2 Jan
AU$309
1 Jan - 2 Jan 2026
includes taxes & fees
With a stay at Omni Boston Hotel at the Seaport, you'll be centrally located in Boston, a 9-minute walk from Harpoon Brewery and 11 minutes by foot from Seaport ...
Opens in a new windowOmni Boston Hotel at the Seaport
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Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
Fully refundableReserve now, pay when you stay
The price is AU$301 per night from 29 Dec to 30 Dec
AU$301
29 Dec - 30 Dec
includes taxes & fees
Located in Boston (Seaport District), Seaport Hotel Boston is a 3-minute walk from Liberty Wharf and 8 minutes by foot from Institute of Contemporary Art.
Opens in a new windowSeaport Hotel Boston
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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.