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Massachusetts Vacation Rentals

Vacation Rental Homes, Condos, Cabins, Villas & Beach Houses in Massachusetts from top rental companies and trusted homeowners.


It is hard to find more history packed into one state than what can be found in Massachusetts. A Massachusetts vacation can begin and end with historical sites, interactive exhibits, notable land features that welcome outdoor recreation, tours that take you from land to sea and the opportunities to see history come to life at a variety of re-created villages and living history museums.

Reserve a vacation house in Massachusetts for your family and have room to spread out and soak in the culture, the history and the landscape of this great state. Family-friendly activities statewide include children’s museums, beginner-level hiking trails, hands-on history lessons and state parks and national forests that will wow you with their beauty.

Massachusetts is no doubt riddled with some significant moments in history. From the Pilgrims’ landing at Plymouth in 1620 and the first battle of the American Revolution in 1775 where the shot heard ‘round the world was fired to the country’s first commercial railroad in 1826 and Alexander Graham Bell’s telephone invention of 1876, American history is rooted in Massachusetts. So a Massachusetts vacation rental in the stunning Berkshires or a Massachusetts condo rental in bustling Boston, and even a Massachusetts resort on Martha’s Vineyard, will bathe your family in historic sites and lessons about our country’s past which you will be eager to learn.

Famous people (Paul Revere, the Kennedys and Henry David Thoreau) and famous events (the first Thanksgiving, Boston Tea Party, Battle of Bunker Hill and Salem Witch Trials) have made Massachusetts a sought-after stomping ground for families seeking a memorable vacation. The natural scene and rugged outdoors and hundreds of miles of waterfront have lured the outdoorsmen to Massachusetts where they regularly seek a Massachusetts rental in the woods, a Massachusetts condo near the riverfront or a Massachusetts resort by deep-water ports.

Ways to See Massachusetts

Leave the comfort and luxury of your condo in Massachusetts for the open road, wide waterways or narrow hiking trails. Get out and enjoy what surrounds your condo in Massachusetts and be sure to keep your camera handy. The 200-mile New England Scenic Trail traverses 39 communities from Massachusetts to Connecticut. Rivers run north-south and east-west and welcome canoeing, kayaking and even white water rafting. Bike trails are so plentiful that you would be silly to leave the bikes at home when you choose a Massachusetts house rental. The same trails that are open for hiking and biking in summer are filled with cross-country skiers in winter. Rent a cozy condo in Massachusetts or Massachusetts vacation rental with a fireplace in winter and go downhill skiing and snowshoeing. Ski mountains are scattered throughout the Berkshires in western Massachusetts. In the summertime speed downhill on a roller coaster at Six Flags on New England near Springfield, Massachusetts. Rock climbers can take their need for heights to Purgatory Chasm State Reservation in Central Massachusetts. Slow down at Walden Pond northeast of Boston in the Greater Merrimack Valley. A Massachusetts condo rental in Boston could be within walking distance of Fenway Park and the Boston Red Sox. South of Boston is the whaling port of New Bedford, the “City that Lit the World.” Choose a Massachusetts house rental near the Cape Cod Rail Trail and hop one island over to Martha’s Vineyard for excellent fishing. Finally, a vacation house in Massachusetts on Nantucket Island puts you within reach of a bustling wharf with fantastic shopping and dining.

There is clearly much about which to get excited when planning a Massachusetts vacation. From the Atlantic Ocean to the New York state line and the islands of the southern coast to Vermont, explore every inch of this history-filled state with your family and enjoy marvelous accommodations at a Massachusetts resort, house or condo rental.