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.

Explore Massachusetts house rentals, condo rentals, studios, and more

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House rentals

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Condo rentals

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Studios

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Massachusetts vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Main Street Upper
2 Bed | 2 Bath | Sleeps 7

Main Street Upper - Vineyard Haven, MA

$451 avg / night
4.25 (20)
A Little Piece of History
3 Bed | 3 Bath | Sleeps 6

A Little Piece of History - Boston, MA

$373 avg / night
4.62 (32)
Goat Hill Cottage
3 Bed | 2 Bath | Sleeps 8

Goat Hill Cottage - Beverly, MA

$457 avg / night
4.5 (18)
Herring Brook
3 Bed | 2 Bath | Sleeps 6

Herring Brook - Eastham, MA

$392 avg / night
4.17 (18)
Island Time
1 Bed | 1 Bath | Sleeps 4

Island Time - Vineyard Haven, MA

$386 avg / night
4.87 (23)

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Recent Massachusetts vacation rental reviews

Perect space for 4 people. Was quaint quiet and very accommodating.
Paula g. | Jan 2025
House was perfect for our 2 families. The teens had their own space downstairs, and the kitchen upstairs was large and had everything you could think of! We especially liked the 1,000-piece puzzles that brought us together, and a few of us found some books on the bookshelves to relax with. Showers were clean, great pressure, and thermostats were responsive. Wonderful place to be and to start the new year!
Regina B. | Jan 2025
This is my third time staying at the Lemonade Stand and it never disappoints. It's in a beautiful, natural setting, and I love the access to Lambert's Cove, my favorite beach on the island. I always appreciate the Clyde Butcher art - gorgeous every time! I love an island home that doesn't feel the need to cover everything with beach/nautical puns because I don't need a cross-stitched "Seas the Day" applique to know I'm near the ocean! :) Thank you for another beautiful, restful stay!
Jenkins L. | Jan 2025
Massachusetts Frequently Asked Questions

Yes, 173 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. 620 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 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 worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Massachusetts, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
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

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Travel Guide: Things to do in Cape Cod, MA

The Best Places to See Fall Foliage in New England