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 MA
The price is AU$534 per night from 14 May to 15 May
AU$534
14 May - 15 May
includes taxes & fees
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.
Opens in a new windowPlymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Peace and quiet on the lake

Peace and quiet on the lake

Becket MA
With a stay at this vacation home in Becket (Sherwood Forest), you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.
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Opens in a new windowPeace and quiet on the lake
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

Amherst MA
The price is AU$265 per night from 17 May to 18 May
AU$265
17 May - 18 May
includes taxes & fees
With a stay at this vacation home, you'll be centrally located in Amherst, within a 5-minute drive of University of Massachusetts Amherst and Puffers Pond South ...
Opens in a new windowkimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley
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Relaxing Getaway: Entire 3-BR Home w/ Fireplace

Relaxing Getaway: Entire 3-BR Home w/ Fireplace

Marlborough MA
The price is AU$606 per night from 3 June to 4 June
AU$606
3 June - 4 June
includes taxes & fees
Located in Marlborough, this vacation home is within a 5-minute drive of Callahan State Park and Old Grist Mill Museum.
Opens in a new windowRelaxing Getaway: Entire 3-BR Home w/ Fireplace
Charming cottage, walk to downtown waterfront, large deck, outdoor seating, and grill

Charming cottage, walk to downtown waterfront, large deck, outdoor seating, and grill

Plymouth MA
A stay at this vacation home places you in the heart of Plymouth, within a 10-minute walk of Harlow Old Fort House and Stephens Field Beach.
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Opens in a new windowCharming cottage, walk to downtown waterfront, large deck, outdoor seating, and grill
Cozy 1-bedroom house in overlooking the river close to downtown Northampton

Cozy 1-bedroom house in overlooking the river close to downtown Northampton

Northampton MA
With a stay at this vacation home in Northampton, you'll be within a 15-minute drive of University of Massachusetts Amherst and Connecticut River.
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Opens in a new windowCozy 1-bedroom house in overlooking the river close to downtown Northampton
Centrally located in the heart of Boston near T

Centrally located in the heart of Boston near T

Boston MA
The price is AU$741 per night from 19 May to 20 May
AU$741
19 May - 20 May
includes taxes & fees
With a stay at this vacation home in Boston (Dorchester), you'll be a 4-minute drive from Northeastern University and 6 minutes from Boston Harbor.
Opens in a new windowCentrally located in the heart of Boston near T
Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat

Great Barrington MA
The price is AU$442 per night from 14 May to 15 May
AU$442
14 May - 15 May
includes taxes & fees
Located in Great Barrington, this vacation home is on a river, a short 4-minute walk from Monument Mountain Reservation and within 1 minutes by car from Housatonic ...
Opens in a new windowCozy Riverside Berkshires Retreat
Nantucket - edge of town

Nantucket - edge of town

Nantucket MA
With a stay at this vacation home in Nantucket, you'll be within a 5-minute drive of Loines Observatory and Nantucket Historical Association.
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Opens in a new windowNantucket - edge of town
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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
5856 Holiday Homes
Lowest Price
AU$204
Highest Price
AU$741
Popular accommodation
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay, Peace and quiet on the lake, kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley, Relaxing Getaway: Entire 3-BR Home w/ Fireplace, Charming cottage, walk to downtown waterfront, large deck, outdoor seating, and grill, Cozy 1-bedroom house in overlooking the river close to downtown Northampton, Centrally located in the heart of Boston near T, Cozy Riverside Berkshires Retreat, Nantucket - edge of town

Top trending hotels in Massachusetts

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
1 Seaport Lane Boston MA
The price is AU$458 per night from 25 May to 26 May
AU$458
25 May - 26 May
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
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$204 per night from 25 May to 26 May
AU$204
25 May - 26 May
includes taxes & fees
Located in Boston (South End), The Revolution Hotel is within a 10-minute walk of Copley Square and Copley Place.
Opens in a new windowThe Revolution Hotel
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$331 per night from 29 May to 30 May
AU$331
29 May - 30 May
includes taxes & fees
With a stay at Omni Boston Hotel at the Seaport, you'll be centrally located in Boston, a short 10-minute walk from Harpoon Brewery and 14 minutes by foot from ...
Opens in a new windowOmni Boston Hotel at the Seaport
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The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
505 Washington Street Boston MA
Fully refundableReserve now, pay when you stay
The price is AU$380 per night from 25 May to 26 May
AU$380
25 May - 26 May
includes taxes & fees
With a stay at The Godfrey Hotel Boston, you'll be centrally located in Boston, steps from The Freedom Trail and 3 minutes by foot from Boston Common.
Opens in a new windowThe Godfrey 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.

More ways to explore Massachusetts

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^Subject to availability and chosen travel dates.