Book Holiday Homes in Eastern 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^

Featured Holiday Homes in Eastern Massachusetts

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

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

Salem
Located in Salem, this vacation home is by the sea, within a 5-minute walk of Salem Maritime National Historic Site and New England Pirate Museum.
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC
Modern & Walkable to city sights.  A 4-bedroom house in wonderful Boston

Modern & Walkable to city sights. A 4-bedroom house in wonderful Boston

Boston
With a stay at this vacation home in Boston (Charlestown), you'll be within a 5-minute drive of TD Garden and Faneuil Hall Marketplace.
Modern & Walkable to city sights. A 4-bedroom house in wonderful Boston
Charming home with deck- walkable to transit, shops & restaurants

Charming home with deck- walkable to transit, shops & restaurants

Newton
With a stay at this vacation home in Newton (Newton Upper Falls), you'll be within a 15-minute drive of Fenway Park and Harvard University.
Charming home with deck- walkable to transit, shops & restaurants
Save an average of 15% on thousands of hotels when you're signed in
Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach

Gloucester
Located in Gloucester, this vacation home is by the sea, a 3-minute walk from Plum Cove Beach and within a 5-minute drive of Halibut Point State Park.
Beach Life Bliss - steps to the beach
Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace

Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace

Swampscott
With a stay at this vacation home in Swampscott, you'll be within a 5-minute drive of Salem Harbor and Salem State College.
Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace
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
OLD TOWN CHARM.  
Sleeps 4- 2 bedrooms - 2.5 baths

OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths

Marblehead
Located in Marblehead, this vacation home is by the sea, within a 5-minute walk of Marblehead Museum & Historical Society and King Hooper Mansion.
OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths
Waterfront on Lake!  6 bd, 2 bth.  Central Air.  Huge Deck.  Paddle boat!

Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!

East Falmouth
When you stay at this vacation home in East Falmouth, you'll be on the waterfront, within a 5-minute drive of Cape Cod Winery and Cape Cod Country Club.
Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!
Dog-friendly, spacious coastal retreat with large deck & W/D - walk to beaches

Dog-friendly, spacious coastal retreat with large deck & W/D - walk to beaches

Scituate
When you stay at this vacation home in Scituate, you'll be by the sea, within a 10-minute walk of Sand Hills Beach and Museum Beach.
Dog-friendly, spacious coastal retreat with large deck & W/D - walk to beaches
Don't see what you're looking for?
See all available properties in Eastern Massachusetts
View all properties
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
338 Holiday Homes
Lowest Price
AU$255
Highest Price
AU$356
Popular accommodation
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC , Modern & Walkable to city sights. A 4-bedroom house in wonderful Boston, Charming home with deck- walkable to transit, shops & restaurants, Beach Life Bliss - steps to the beach, Beautiful coastal 5-BR in Swampscott - 5 mins to beach, Wifi, gas fireplace, LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches, OLD TOWN CHARM. Sleeps 4- 2 bedrooms - 2.5 baths, Waterfront on Lake! 6 bd, 2 bth. Central Air. Huge Deck. Paddle boat!, Dog-friendly, spacious coastal retreat with large deck & W/D - walk to beaches

Top trending hotels in Eastern Massachusetts

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$356 per night from 13 Feb to 14 Feb
AU$356
includes taxes & fees
13 Feb - 14 Feb
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.
Seaport Hotel Boston
Omni Boston Hotel at the Seaport

Omni Boston Hotel at the Seaport

4 out of 5
450 Summer Street, Boston, MA
The price is AU$274 per night from 23 Feb to 24 Feb
AU$274
includes taxes & fees
23 Feb - 24 Feb
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 ...
Omni Boston Hotel at the Seaport
Hilton Boston Park Plaza

Hilton Boston Park Plaza

4 out of 5
50 Park Plaza, Boston, MA
Fully refundableReserve now, pay when you stay
The price is AU$255 per night from 9 Feb to 10 Feb
AU$255
includes taxes & fees
9 Feb - 10 Feb
With a stay at Hilton Boston Park Plaza, you'll be centrally located in Boston, steps from Boston Public Garden and within a 5-minute walk of Newbury ...
Hilton Boston Park Plaza
Save an average of 15% on thousands of hotels when you're signed in
The Dagny Boston

The Dagny Boston

4 out of 5
89 Broad Street, Boston, MA
Fully refundableReserve now, pay when you stay
The price is AU$284 per night from 31 Jan to 1 Feb
AU$284
includes taxes & fees
31 Jan - 1 Feb
With a stay at The Dagny Boston, you'll be centrally located in Boston, within a 10-minute walk of New England Aquarium and Faneuil Hall Marketplace.
The Dagny Boston
Don't see what you're looking for?
See all available properties in Eastern Massachusetts
View all properties
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.