Book Holiday Homes in Massachusetts
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Explore these top cities in Massachusetts
Featured Holiday Homes in Massachusetts

3 Mi to Beach: Historic Farmhouse on Cape Cod!

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

Walk to Beach. Private Nature and Bird Watching Trail. Quiet.

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

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

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Great Home Close to Craigville Beach

Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants

Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi
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 | 6639 Holiday Homes |
---|---|
Lowest Price | NZ$342 |
Highest Price | NZ$1,403 |
Popular accommodation | 3 Mi to Beach: Historic Farmhouse on Cape Cod!, "Captain's Lookout" on Wonson Cove, Rocky Neck - Gloucester, Walk to Beach. Private Nature and Bird Watching Trail. Quiet., Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC , Spacious 5-bedroom 5 bath house in charming Marblehead & close to the ocean, 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Great Home Close to Craigville Beach, Chatham! 3BR house, large quiet yard, 5 min to beach, walk to shops, restaurants, Large Luxury Condo/Townhouse Center of South Boston W/ Free Parking & WiFi |
Top trending hotels in Massachusetts

Omni Boston Hotel at the Seaport

citizenM Boston North Station

citizenM Boston Back Bay

The Revolution Hotel
More ways to explore Massachusetts
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.