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Massachusetts Vacation Rentals

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  3. Massachusetts

Top Vacation Destinations in Massachusetts

  • Boston3,441 Properties
  • Nantucket3,241 Properties
  • Provincetown2,272 Properties
  • Eastham1,663 Properties
  • Dennis Port1,632 Properties
  • Chatham1,575 Properties
  • Brewster1,460 Properties
  • Wellfleet1,323 Properties
  • Orleans1,230 Properties

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Massachusetts Travel Guide

Massachusetts, New England, is a state packed with cool cities, historic sites, sandy beaches, surrounding mountains and great art museums. It’s one of the most historically important locations for the history of the pilgrims and is home to the first pilgrim landing site, alongside tons of important sites to do with the history of the American Revolution. It’s a state that has everything, you won’t be disappointed.

Things to Do in Massachusetts

Start your trip in Boston, one of the most buzzing cities in the US. When in Boston you can find everything from history to culture and entertainment. You can also explore the Freedom Trail, which is a walking route that will take you to some of the country’s most important sites from the American Revolution, including Bunker Hill, which commemorates the first major battle in 1775. Be sure to visit the African American Heritage Trail too, which looks at Boston’s 19th-century African American community.

Meanwhile, if fine art tickles your fancy, head to the Museum of Fine Arts or the Institute of Contemporary Art – both of which offer interesting exhibitions, sometimes politically provocative.

Time for some fresh sea air? Beach lovers can head to Cape Cod, and the nearby islands of Nantucket and Martha’s Vineyard, where you’ll find miles of sandy beaches.

Best Places to Stay in Massachusetts

The best place to stay in Massachusetts is in Boston, where you can explore the area’s rich history. Boston is also a one to two hour drive to the beaches of Cape Cop, making it a great place to base yourself.

Best Time to Visit Massachusetts

The best time to visit Massachusetts is in the fall, when you can see the incredible array of autumnal colors in the foliage. Spring and summer are also great times if you want to enjoy the beaches and the historic walking trails.

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Price and Availability in Massachusetts

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The cheapest day to stay at a vacation rental in Massachusetts tends to be Tuesday, while the most expensive day tends to be Saturday. Vacation homes in Massachusetts tend to be busiest on Saturdays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Massachusetts is in July, while the cheapest month is in January. The most popular time to book a vacation rental in Massachusetts is in the high season in August. Massachusetts has its low season in January, when less people are visiting and the vacation home occupancy rate drops.
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What Expert Travelers Think

  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

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    Sarah PoolTammymum
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  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
    Middle Class Dad

  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

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Destinations in Massachusetts

  • Somerville1,045 Properties
  • Edgartown1,004 Properties
  • West Yarmouth913 Properties
  • Cambridge870 Properties
  • Falmouth869 Properties
  • Mashpee859 Properties
  • Hyannis808 Properties
  • South Yarmouth791 Properties
  • Brookline765 Properties
  • Tisbury714 Properties
  • Plymouth678 Properties
  • Rockport673 Properties
  • East Falmouth670 Properties
  • West Dennis627 Properties
  • North Truro612 Properties
  • Gloucester608 Properties
  • South Chatham599 Properties
  • Lenox539 Properties
  • Harwich533 Properties
  • Worcester492 Properties
  • Salem474 Properties
  • Dennis472 Properties
  • Harwich Port463 Properties
  • East Sandwich442 Properties
  • Centerville441 Properties
  • Hancock430 Properties
  • Revere415 Properties
  • Great Barrington411 Properties
  • Vineyard Haven401 Properties
  • Waltham389 Properties
  • Lee368 Properties
  • Quincy357 Properties
  • Northampton357 Properties
  • Sandwich352 Properties
  • Newton341 Properties
  • Truro339 Properties
  • Medford326 Properties
  • Watertown323 Properties
  • Williamstown315 Properties
  • Newburyport312 Properties
  • Marblehead304 Properties
  • Pittsfield300 Properties
  • South Dennis290 Properties
  • North Falmouth267 Properties
  • Chelsea266 Properties
  • Amherst257 Properties
  • Stockbridge246 Properties
  • Marshfield242 Properties
  • Osterville232 Properties
  • Barnstable232 Properties
  • Arlington231 Properties
  • Wareham207 Properties
  • Scituate200 Properties
  • West Harwich198 Properties
  • Woburn186 Properties
  • Chilmark172 Properties
  • Bourne164 Properties
  • Sturbridge155 Properties
  • Fairhaven138 Properties
  • Winthrop130 Properties
  • Ipswich120 Properties
  • Westport117 Properties
  • West Stockbridge109 Properties
  • Marlborough108 Properties
  • Hull97 Properties
  • New Marlborough89 Properties
  • Sheffield81 Properties
  • Manchester76 Properties
  • Springfield65 Properties
  • Concord65 Properties
  • Sudbury48 Properties
  • Ashburnham33 Properties
  • Cheshire22 Properties
  • Hubbardston8 Properties