Massachusetts Vacation Rentals

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Make Massachusetts your next getaway

From its founding in 1788 to its position today as a science mecca, Massachusetts delights visitors wanting to explore our nation's history, and offers great spots to dine and enjoy the outdoors. With a coast spanning nearly 200 miles, encompassing grassy heaths and rugged slopes, to inland lakes, streams, meadows, and mountains, Massachusetts boasts myriad places to escape from the every day. So, enjoy your time in this lush and vibrant state - home of John F. Kennedy, Nathaniel Hawthorne and Dr. Seuss - at one of our picturesque Massachusetts vacation rentals.

Top Massachusetts property types

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House rentals

View 420 House rentals
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Condo rentals

View 48 Condo rentals
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Studios

View 33 Studios

Popular amenities for Massachusetts vacation rentals

Popular
Dog-friendly Hot tub Internet
The Lemonade Stand
1 Bedroom | 1 Bath | Sleeps 4

The Lemonade Stand - West Tisbury, MA

$194 avg / night
(excludes fees and taxes)
4.53 (45)
Oak Bluffs Beauty
4 Bedroom | 3 Bath | Sleeps 10

Oak Bluffs Beauty - Oak Bluffs, MA

$352 avg / night
(excludes fees and taxes)
4.54 (71)
Longview House
4 Bedroom | 2.5 Bath | Sleeps 9

Longview House - Gloucester, MA

$249 avg / night
(excludes fees and taxes)
4.17 (6)
Paula's Suite
2 Bedroom | 2 Bath | Sleeps 4

Paula's Suite - Gloucester, MA

$206 avg / night
(excludes fees and taxes)
4.77 (31)
Twelve Trees
3 Bedroom | 2 Bath | Sleeps 6

Twelve Trees - Truro, MA

$224 avg / night
(excludes fees and taxes)
4.78 (18)

View 557 more homes

Recent Massachusetts guest reviews

⸻ We really enjoyed our stay at this home. The house itself is extremely clean, quiet, and very secluded—exactly what we were hoping for. Once we were inside, everything was perfect and we had an amazing trip. One thing I would recommend for future guests is to let the host know if you’ll be arriving after dark. The property is very secluded, and the driveway can be difficult to find at night. There are no street lights, and figuring out how to get through the gate and locate the keypad in the dark was a bit challenging. There is a flood light near the driveway, but it didn’t help much with visibility at the entrance. We did call in for assistance, and the representative was wonderful—stayed on the phone with us and guided us until we were in safely. Overall, it was a great stay and we would absolutely return. Just plan ahead if you’re arriving after sunset!
Tonya P. | Nov 2025
I stayed with a friend at this location. It’s cute and quaint. Loved the proximity to the restaurants and shops. It’s an easy drive to Salem and Gloucester. I had trouble opening the door (because I wasn’t accustomed to the type of lock that was on the door). Once customer service helped me figure it out, it was fine. We arrived once the sun went down so it was dark and cold so I’m sure that added to my lack of cognitive skills to open the door. Beware the screen door as it shuts once you release it. All is good with the property and we enjoyed our stay.
Leslie A. | Nov 2025
The town was great a lot see! Very pretty!
Linda W. | Nov 2025
Massachusetts vacation rental FAQ

Yes, 149 of our Massachusetts homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 562 of our Massachusetts vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Massachusetts vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find the check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Massachusetts team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No problem, plans can change. For more information, please read our cancellation policy. If you have a Vacasa reservation for Massachusetts, log in to Trip Manager to explore the options available for your specific trip.

Book confidently. Stay comfortably.

Vacasa Guest Value Prop icon: 24-7
24/7 guest service
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Seamless check-in
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Professional cleaning

Visiting Boston, Massachusetts

Boston is the largest city in the state, but still retains much of its historic flavor. Tour the Freedom Trail, a historic 2.5-mile journey commemorating the brave men who fought in the American Revolution. Relive John F. Kennedy's heyday at the John F. Kennedy Memorial Library, or head to Beacon Hill and admire the many well-preserved buildings and monuments to our country's founding. Or enjoy a baseball game at historic Fenway Park, one of the last remaining vintage ballparks in the nation. A stay in one of our Boston vacation rentals gives you a comfortable place to call home while you explore the city - which is important, as you'll need more than a week to see all the sites!

Find a small-town getaway in Massachusetts

Looking to avoid the big city? Explore picturesque Cape Cod, with its myriad beach towns, from gay-friendly Provincetown to Nantucket. Martha's Vineyard lures thousands of tourists each year, thanks to its quaint atmosphere, lovely vacation rentals, and gorgeous beaches. North Adams plays host to Mass MoCA every summer, and the Norman Rockwell Museum in Stockbridge delights lovers of Americana. Find inspiration at Walden Pond State Reservation in Concord, home to Henry David Thoreau for nearly two years. Head to historic Quincy, birthplace of two presidents, and stroll through the Adams National Historic Park. 

History and the outdoors collide in verdant Massachusetts. It's New England at its finest, so definitely plan a stay at one of our Massachusetts vacation rentals!

Massachusetts travel inspiration

The ultimate guide to a dog-friendly East Coast vacation

Travel Guide: Things to do in Cape Cod, MA

The Best Places to See Fall Foliage in New England