24,741 Massachusetts Holiday Rentals

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Compare Massachusetts holiday rentals from 15 rental sites including HomeAway, Booking.com, TripAdvisor and more, ranging from $25 to $987654 a night.

Information about Massachusetts

About Massachusetts

When you think of Massachusetts you probably picture historic Colonial sites, sandy beaches and the sprawling capital city of Boston. However, the Bay State is also known for its charming small towns and beautiful weekend getaways. Home to Harvard University and Plymouth Rock, Massachusetts is the foundation of U.S. history with modern luxuries mixed in. A trip to Massachusetts isn’t complete without a drive down Cape Cod and a swim in the crisp Atlantic Ocean. Book your trip today and experience all that Massachusetts has to offer!

Things to do in Massachusetts

Visiting Lexington and Concord, where the Revolutionary War started, is a must for any history-junkies’ trip to Massachusetts. However, the city of Boston is a goldmine for historic attractions including The Paul Revere House and the Bunker Hill Monument. Take a unique tour of “Bean Town” on the famous Boston Duck Tours. These large vehicles go on land and sea and give a great overview of the city’s history. Other popular activities in Boston include watching the MLB Boston Red Sox at Fenway Park or cheering on the NFL New England Patriots.

Best cities to visit in Massachusetts

Boston ranks the highest on the best cities to visit in Massachusetts, however, there are many other cities that deserve a visit. Although it’s only a quarter the population of Boston, Worcester has plenty of beauty and attractions to hold its own. Check out the Green Hill Park and the Bancroft Tower, Massachusetts’ own miniature castle. You should also take a visit to New Bedford, Massachusetts, which is known for its whaling history and quaint wineries. No matter what city you visit in Massachusetts you will be welcoming with history, culture and fun times!

Best small towns in Massachusetts

If you’re looking for some R&R, Martha’s Vineyard in Cape Cod is the perfect getaway. A popular vacation destination for the Kennedys, Martha’s Vineyard Is a picturesque island south of Cape Cod. On the tip of Cape Cod’s hook sits the eccentric town of Provincetown. Walk along Commercial Street to see the shop and local artists. Perhaps less charming, and a bit more wicked, the small town of Salem ranks for one of Massachusetts’ best small towns to visit. Known for the Salem witch trials, this town has several museums and a massive Halloween celebration. Stay a day or a week in any of these small towns with vacation rentals from Tripping!

Best lake vacations in Massachusetts h3>

Make your lake vacation dream a reality at some of the most beautiful lakes in the United States. Walden Pond in Concord, Massachusetts is actually a lake most popular for being the subject of Henry David Thoreau’s “Walden.” Read your favorite book by this breathtaking lake or go fishing for rainbow trout. Although there is no camping at the state reservation, there are lodges and vacation rentals nearby. Cape Cod has dozens of lakes to explore including Wequaquet Lake in Barnstable. Activities here include kayaking and fishing with camping spots nearby!

Best National Parks in Massachusetts h3>

Many of the 16 National Parks in Massachusetts are historical. Take a visit to the Bunker Hill Monument or the Charlestown Navy Yard at the Boston National Historical Park. Then, explore historic sites from the American Revolution at the Minute Man National Historic Park. Many of these sites offer tours and even reenactments of the time period. Finish off your tour of National Parks on the sandy beaches of Cape Cod, which are also protected and is considered a national seashore with six beaches and beautiful views included.

Vacation Rentals in Massachusetts

Find the best Massachusetts vacation rentals with Tripping.com. Choose from 26489 rentals, from studio apartments to luxurious condos to entire cabin homes. Book in advance or book instantly with properties marked as “Instabook,” with prices ranging from $25 a night to $987654 a night.

Our Tripping.com vacation rentals will save you hundreds, offering more amenities than the average hotel room. Going on a business trip? 16120 of homes in Massachusetts offer high-speed wifi internet so you won’t miss a beat. Travelling with kids? Have them splash around in any of the 1653 rentals with pool or jacuzzi, or relax with the family in one of the 15915 homes with cable TV.

For all those dog lovers and cat lovers, Massachusetts offers 4026 pet-friendly vacation rentals at an affordable price. Book the perfect vacation home that best matches your budget and accommodation style. For the ultimate stay, check out our listings now to grab the latest deals.

Search properties from 15 rental sites in Massachusetts where the top providers in that area are HomeAway, Booking.com, and TripAdvisor. There are 9830 HomeAway rentals, 7289 Booking.com short term rentals and 4574 TripAdvisor vacation rentals.