Book Holiday Homes in Massachusetts

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Featured Holiday Homes in Massachusetts

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Plymouth
The price is AU$602 per night from 4 May to 5 May
AU$602
includes taxes & fees
4 May - 5 May
With a stay at this vacation home in Plymouth, you'll be by the ocean, within a 15-minute drive of Cape Cod Beaches and Manomet Beach.
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy

West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy

West Roxbury
With a stay at this vacation home, you'll be centrally located in Boston, within a 10-minute drive of Boston College and Northeastern University.
West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy
LUXURIOUS New Cottage!  5-min. walk to Main St. And Harbor Beaches

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

Nantucket
A stay at this vacation home places you in the heart of Nantucket, steps from Greater Light Garden and Fire Hose Cart House.
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches
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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 AU$709 per night from 5 May to 6 May
AU$709
includes taxes & fees
5 May - 6 May
With a stay at this vacation home in Chatham, you'll be by the sea, within a 5-minute drive of Cape Cod Beaches and Hardings Beach.
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi

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

Boston
With a stay at this vacation home, you'll be centrally located in Boston, within a 5-minute drive of Boston Convention and Exhibition Center and Boston ...
Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
Clean, Contemporary Escape | Near T

Clean, Contemporary Escape | Near T

Boston
With a stay at this vacation home in Boston (Roxbury), you'll be within a 5-minute drive of Northeastern University and Fenway Park.
Clean, Contemporary Escape | Near T
2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything

2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything

Chelsea
The price is AU$725 per night from 5 May to 6 May
AU$725
includes taxes & fees
5 May - 6 May
With a stay at this vacation home, you'll be centrally located in Chelsea, within a 10-minute drive of Encore Boston Harbor and TD Garden.
2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!

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

Salem
The price is AU$440 per night from 6 May to 7 May
AU$440
includes taxes & fees
6 May - 7 May
This vacation home is in the heart of Salem, within a 5-minute walk of Salem Witch Trials Memorial and Salem Witch Museum.
Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!
Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left

Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left

Quincy
When you stay at this vacation home in Quincy, you'll be by the ocean, within a 15-minute drive of Northeastern University and Boston Harbor.
Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left
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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.

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 Massachusetts vacation homes are the perfect way for you to wing it.

Holiday houses in 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 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 Massachusetts adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in 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 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.

Massachusetts Holiday Homes essential information

Accommodation
6208 Holiday Homes
Lowest Price
AU$201
Highest Price
AU$725
Popular accommodation
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay, West Roxbury Retreat –Near Downtown Boston, Steps to Train & Bus, Spacious&Comfy, LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches, Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK, Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi, Clean, Contemporary Escape | Near T, 2BR with a king, queen-beds sofa bed 65’’TV free parking close to everything , Prime Location!WALK TO WATER & HISTORIC DISTRICT!PRIVATE Large first floor apt!, Luxury Oceanfront Bayside Jewel-🔥🔥 20% off- Limited space left

Top trending hotels in Massachusetts

The Revolution Hotel

The Revolution Hotel

3.5 out of 5
40 Berkeley Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is AU$288 per night from 4 May to 5 May
AU$288
includes taxes & fees
4 May - 5 May
Located in Boston (South End), The Revolution Hotel is within a 10-minute walk of Copley Place and Newbury Street.
The Revolution Hotel
Four Points by Sheraton Boston Newton

Four Points by Sheraton Boston Newton

3.5 out of 5
320 Washington Street, Newton, MA
The price is AU$201 per night from 11 May to 12 May
AU$201
includes taxes & fees
11 May - 12 May
Located in Newton (Newton Corner), Four Points by Sheraton Boston Newton is within a 10-minute drive of Boston University and Boston College.
Four Points by Sheraton Boston Newton
citizenM Boston Back Bay

citizenM Boston Back Bay

4 out of 5
408 Newbury street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is AU$342 per night from 4 May to 5 May
AU$342
includes taxes & fees
4 May - 5 May
With a stay at citizenM Boston Back Bay in Boston (Fenway–Kenmore), you'll be steps from Newbury Street and 10 minutes by foot from Northeastern University.
citizenM Boston Back Bay
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Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St, Boston, MA
The price is AU$414 per night from 4 May to 5 May
AU$414
includes taxes & fees
4 May - 5 May
Harborside Inn Of Boston is in the heart of Boston, within a 5-minute walk of Faneuil Hall Marketplace and Quincy Market.
Harborside Inn Of Boston
Don't see what you're looking for?
See all available properties in Massachusetts
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.