Book Holiday Homes in Carlisle

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Featured Holiday Homes in Carlisle

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 5 Jan to 6 Jan
AU$827
5 Jan - 6 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
Relaxing Getaway: Entire 3-BR Home w/ Fireplace

Relaxing Getaway: Entire 3-BR Home w/ Fireplace

Marlborough MA
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
Beautifully Renovated Cozy Home

Beautifully Renovated Cozy Home

Medford MA
With a stay at this vacation home in Medford, you'll be a 4-minute drive from Tufts University and 9 minutes from Encore Boston Harbor.
Opens in a new windowBeautifully Renovated Cozy Home
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Spacious, New Renovation | Near T

Spacious, New Renovation | Near T

Boston MA
With a stay at this vacation home in Boston (Dorchester), you'll be a 4-minute drive from Northeastern University and 6 minutes from Copley Square.
Opens in a new windowSpacious, New Renovation | Near T
Clean, Contemporary Escape | Near T

Clean, Contemporary Escape | Near T

Boston MA
With a stay at this vacation home in Boston (Roxbury), you'll be within a 5-minute drive of Fenway Park and Copley Square.
Opens in a new windowClean, Contemporary Escape | Near T
Newly Renovated Luxury 3-Bed 2-Bath Home with Easy Airport Access

Newly Renovated Luxury 3-Bed 2-Bath Home with Easy Airport Access

Framingham MA
The price is AU$395 per night from 1 Jan to 2 Jan
AU$395
1 Jan - 2 Jan 2026
includes taxes & fees
Located in Framingham, this vacation home is within a 5-minute drive of Josephine Kochnowicz Clock Tower and Old Danforth Street Bridge.
Opens in a new windowNewly Renovated Luxury 3-Bed 2-Bath Home with Easy Airport Access
Free 2 Car Parking at this 3 bedroom apartment. Close to a park. Great location

Free 2 Car Parking at this 3 bedroom apartment. Close to a park. Great location

Cambridge MA
The price is AU$671 per night from 1 Jan to 2 Jan
AU$671
1 Jan - 2 Jan 2026
includes taxes & fees
With a stay at this vacation home in Cambridge (The Port), you'll be within a 5-minute drive of Harvard University and Massachusetts Institute of ...
Opens in a new windowFree 2 Car Parking at this 3 bedroom apartment. Close to a park. Great location
West Roxbury Retreat–Near Downtown Boston, Steps to Train & Bus,member only deal

West Roxbury Retreat–Near Downtown Boston, Steps to Train & Bus,member only deal

West Roxbury MA
With a stay at this vacation home, you'll be centrally located in Boston, within a 10-minute drive of Northeastern University and Boston College.
Opens in a new windowWest Roxbury Retreat–Near Downtown Boston, Steps to Train & Bus,member only deal
Cozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free Parking

Cozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free Parking

Medford MA
The price is AU$814 per night from 26 Dec to 27 Dec
AU$814
26 Dec - 27 Dec
includes taxes & fees
With a stay at this vacation home in Medford (South Medford), you'll be a 2-minute drive from Tufts University and 7 minutes from Harvard University.
Opens in a new windowCozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free Parking
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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.

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

Holiday houses in Carlisle 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 Carlisle 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 Carlisle adventures, obvs.

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

Carlisle Holiday Homes essential information

Accommodation
349 Holiday Homes
Lowest Price
AU$290
Highest Price
AU$827
Popular accommodation
Waterfront House Minutes from the Boston Downtown, Airport, Encore Casino, Relaxing Getaway: Entire 3-BR Home w/ Fireplace, Beautifully Renovated Cozy Home, Spacious, New Renovation | Near T, Clean, Contemporary Escape | Near T, Newly Renovated Luxury 3-Bed 2-Bath Home with Easy Airport Access, Free 2 Car Parking at this 3 bedroom apartment. Close to a park. Great location, West Roxbury Retreat–Near Downtown Boston, Steps to Train & Bus,member only deal, Cozy 4BR Home by Tufts w/ Subway Access to Downtown, MIT, Harvard + Free Parking

Top trending hotels in Carlisle

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$290 per night from 18 Jan to 19 Jan
AU$290
18 Jan - 19 Jan 2026
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$319 per night from 25 Dec to 26 Dec
AU$319
25 Dec - 26 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$301 per night from 29 Dec to 30 Dec
AU$301
29 Dec - 30 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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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.

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^Subject to availability and chosen travel dates.