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Popular Massachusetts Vacation Rentals

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House Brewster
e.g. 9/4 - 9/11 (Sat - Sat)
$326 per night
House ∙ 7 guests ∙ 3 bedrooms
Brewster, Brewster Town, Massachusetts
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Apartment Theatre District
e.g. 1/8 - 1/15 (Sat - Sat)
-66%
$300
$102 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Theatre District, Boston, Massachusetts
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House Brewster
e.g. 10/2 - 10/9 (Sat - Sat)
$233 per night
House ∙ 8 guests ∙ 3 bedrooms
Brewster, Brewster Town, Massachusetts
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Apartment Brewster
e.g. 10/2 - 10/9 (Sat - Sat)
$292 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Brewster, Brewster Town, Massachusetts
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Condo Hancock
e.g. 10/23 - 10/30 (Sat - Sat)
$110 per night
Condo ∙ 8 guests ∙ 2 bedrooms
Hancock, Berkshire County, Massachusetts
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House East Harwich
e.g. 9/4 - 9/11 (Sat - Sat)
$275 per night
House ∙ 4 guests ∙ 2 bedrooms
East Harwich, Harwich, Massachusetts
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House West Yarmouth
e.g. 9/18 - 9/25 (Sat - Sat)
-17%
$326
$270 per night
House ∙ 6 guests ∙ 3 bedrooms
West Yarmouth, Yarmouth, Massachusetts
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House Brewster
e.g. 9/4 - 9/11 (Sat - Sat)
$373 per night
House ∙ 8 guests ∙ 4 bedrooms
Brewster, Brewster Town, Massachusetts
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Apartment Brewster
e.g. 9/18 - 9/25 (Sat - Sat)
$365 per night
Apartment ∙ 6 guests ∙ 3 bedrooms
Brewster, Brewster Town, Massachusetts
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Vacation rentals with Wi-Fi

Condo Internet Hancock
e.g. 10/23 - 10/30 (Sat - Sat)
$110 per night
Condo ∙ 8 guests ∙ 2 bedrooms
Hancock, Berkshire County, Massachusetts
Internet
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Cottage Internet Brewster
e.g. 9/11 - 9/18 (Sat - Sat)
$205 per night
Cottage ∙ 4 guests ∙ 1 bedroom
Brewster, Brewster Town, Massachusetts
Internet
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House Internet Brewster
e.g. 10/2 - 10/9 (Sat - Sat)
$268 per night
House ∙ 8 guests ∙ 3 bedrooms
Brewster, Brewster Town, Massachusetts
Internet
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Vacation rentals and apartments with air conditioning

Apartment Aircondition West Dennis
e.g. 9/11 - 9/18 (Sat - Sat)
$281 per night
Apartment ∙ 8 guests ∙ 3 bedrooms
West Dennis, Dennis, Massachusetts
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House Aircondition Northwest Harwich
e.g. 9/25 - 10/2 (Sat - Sat)
-44%
$504
$284 per night
House ∙ 8 guests ∙ 4 bedrooms
Northwest Harwich, Harwich, Massachusetts
Aircondition
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Apartment Aircondition Brewster
e.g. 9/4 - 9/11 (Sat - Sat)
$233 per night
Apartment ∙ 4 guests ∙ 2 bedrooms
Brewster, Brewster Town, Massachusetts
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Apartments and vacation rentals with a kitchen

Apartment Kitchen Theatre District
e.g. 2/12 - 2/19 (Sat - Sat)
-67%
$314
$103 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Theatre District, Boston, Massachusetts
Kitchen
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Apartment Kitchen Brewster
e.g. 9/25 - 10/2 (Sat - Sat)
$243 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
Brewster, Brewster Town, Massachusetts
Kitchen
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Apartment Kitchen Theatre District
e.g. 1/4 - 1/11 (Tue - Tue)
-72%
$282
$80 per night
Apartment ∙ 4 guests ∙ 1 bedroom
Theatre District, Boston, Massachusetts
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Finding the perfect vacation home has never been easier. Tripping.com searches the world's top vacation rental sites to find the best properties in 190 countries worldwide. One search lets you filter, compare and sort over 10 million available vacation rentals from trusted partners including HomeAway, VRBO, TripAdvisor, Booking.com and more. When you use Tripping.com to plan your trip and book your vacation rental, you never have to wonder if you're getting the best deal.

Massachusetts Information

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! <h3>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. </h3>

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