Book Holiday Homes in Massachusetts

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Featured Holiday Homes in 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$1,033 per night from 26 Dec to 27 Dec
AU$1,033
26 Dec - 27 Dec
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...........
Newly Renovated Near Amazing Sunset Beach

Newly Renovated Near Amazing Sunset Beach

Falmouth MA
With a stay at this vacation home in North Falmouth, you'll be within a 5-minute drive of Cape Cod Beaches and Cataumet Arts Center.
Opens in a new windowNewly Renovated Near Amazing Sunset Beach
Spacious 4-bedroom with four and half bathrooms

Spacious 4-bedroom with four and half bathrooms

Worcester MA
The price is AU$776 per night from 22 Dec to 23 Dec
AU$776
22 Dec - 23 Dec
includes taxes & fees
With a stay at this vacation home in Worcester, you'll be within a 5-minute drive of Bowlero Worcester and College of the Holy Cross.
Opens in a new windowSpacious 4-bedroom with four and half bathrooms
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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$827 per night from 19 Jan to 20 Jan
AU$827
19 Jan - 20 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
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

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

Dennis MA
The price is AU$478 per night from 28 Dec to 29 Dec
AU$478
28 Dec - 29 Dec
includes taxes & fees
With a stay at this vacation home in Dennis Port, you'll be by the sea, within a 5-minute drive of Cape Cod Beaches and Cape Cod Theatre Company – Home of the ...
Opens in a new window2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom

Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom

Falmouth MA
With a stay at this vacation home, you'll be centrally located in East Falmouth, within a 5-minute drive of Cape Cod Beaches and Waquoit Bay National Estuarine ...
Opens in a new windowCape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom
FaLL Western Mass Getaway-Airhockey-Firepit

FaLL Western Mass Getaway-Airhockey-Firepit

Colrain MA
The price is AU$1,029 per night from 19 Jan to 20 Jan
AU$1,029
19 Jan - 20 Jan 2026
includes taxes & fees
Located in Colrain, this vacation home is within a 5-minute drive of Arthur A. Smith Covered Bridge and G. William Pitt House and Collection.
Opens in a new windowFaLL Western Mass Getaway-Airhockey-Firepit
Moon Compass Escape – Spacious Cape Cod Retreat

Moon Compass Escape – Spacious Cape Cod Retreat

Sandwich MA
Located in Sandwich, this vacation home is by the sea, within a 10-minute drive of Mashpee Wampanoag Indian Museum and Cotuit Center for the Arts.
Opens in a new windowMoon Compass Escape – Spacious Cape Cod Retreat
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

East Falmouth MA
With a stay at this vacation home in East Falmouth, you'll be on the beach, within a 15-minute drive of Cape Cod Beaches and Cape Cod Winery.
Opens in a new windowBeach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub
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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
6046 Holiday Homes
Lowest Price
AU$260
Highest Price
AU$1,033
Popular accommodation
Ocean Dreams, Waves as far as the eyes can see..........., Newly Renovated Near Amazing Sunset Beach, Spacious 4-bedroom with four and half bathrooms, Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino, 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom, FaLL Western Mass Getaway-Airhockey-Firepit, Moon Compass Escape – Spacious Cape Cod Retreat, Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

Top trending hotels in Massachusetts

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
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$260 per night from 22 Dec to 23 Dec
AU$260
22 Dec - 23 Dec
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
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$314 per night from 21 Dec to 22 Dec
AU$314
21 Dec - 22 Dec
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$305 per night from 21 Dec to 22 Dec
AU$305
21 Dec - 22 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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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.