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Popular Massachusetts Vacation Rentals

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House Edgartown
e.g. 6/4 - 6/11 (Sat - Sat)
$243 per night
House ∙ 6 guests ∙ 3 bedrooms
4.1/5.0 "Very good"
(22 ratings)
Edgartown, Dukes County, Massachusetts
Details
Vrbo
Details
House West Dennis
e.g. 1/15 - 1/22 (Sat - Sat)
$195 per night
House ∙ 6 guests ∙ 3 bedrooms
4.9/5.0 "Excellent"
(24 ratings)
West Dennis, Dennis, Massachusetts
Free cancellation
Details
Vrbo
Details
House Becket
e.g. 8/20 - 8/27 (Sat - Sat)
$185 per night
House ∙ 4 guests ∙ 2 bedrooms
5.0/5.0 "Excellent"
(26 ratings)
Becket, Berkshire County, Massachusetts
Free cancellation
Details
Vrbo
Details
House Brewster
e.g. 11/20 - 11/27 (Sat - Sat)
$143 per night
House ∙ 7 guests ∙ 3 bedrooms
5.0/5.0 "Excellent"
(9 ratings)
Brewster, Brewster Town, Massachusetts
Details
Vrbo
Details
House Wellfleet
e.g. 10/23 - 10/30 (Sat - Sat)
-32%
$250
$171 per night
House ∙ 4 guests ∙ 2 bedrooms
4.7/5.0 "Outstanding"
(45 ratings)
Wellfleet, Barnstable County, Massachusetts
Details
Vrbo
Details
House Harwich Port
e.g. 10/17 - 10/24 (Sun - Sun)
-24%
$222
$169 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0/5.0 "Excellent"
(19 ratings)
Harwich Port, Harwich, Massachusetts
Details
Vrbo
Details
House Salisbury
e.g. 10/23 - 10/30 (Sat - Sat)
$108 per night
House ∙ 5 guests ∙ 2 bedrooms
4.3/5.0 "Very good"
(20 ratings)
Salisbury, Essex County, Massachusetts
Details
Vrbo
Details
House Eastham
e.g. 10/1 - 10/8 (Sat - Sat)
-24%
$206
$157 per night
House ∙ 5 guests ∙ 1 bedroom
4.5/5.0 "Outstanding"
(53 ratings)
Eastham, Orleans Town, Massachusetts
Free cancellation
Details
Vrbo
Details
Apartment Oak Bluffs
e.g. 10/1 - 10/8 (Sat - Sat)
-59%
$490
$200 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.9/5.0 "Excellent"
(27 ratings)
Oak Bluffs, Dukes County, Massachusetts
Details
Vrbo
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Vacation rentals with Wi-Fi

House Internet Tom Nevers
e.g. 12/12 - 12/19 (Sun - Sun)
-28%
$599
$429 per night
House ∙ 6 guests ∙ 2 bedrooms
4.7/5.0 "Outstanding"
(3 ratings)
Tom Nevers, Nantucket, Massachusetts
Internet
Details
Vrbo
Details
Apartment Internet Jamaica Plain
e.g. 1/22 - 1/29 (Sat - Sat)
$170 per night
Apartment ∙ 6 guests ∙ 2 bedrooms
4.8/5.0 "Excellent"
(113 ratings)
Jamaica Plain, Boston, Massachusetts
Free cancellation
Internet
Details
Vrbo
Details
House Internet Ocean Bluff-Brant Rock
e.g. 12/11 - 12/18 (Sat - Sat)
-48%
$329
$171 per night
House ∙ 6 guests ∙ 3 bedrooms
5.0/5.0 "Excellent"
(3 ratings)
Ocean Bluff-Brant Rock, Plymouth County, Massachusetts
Free cancellation
Internet
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Vrbo
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Apartments and vacation rentals with a kitchen

House Kitchen Hull
e.g. 1/1 - 1/8 (Sat - Sat)
-25%
$300
$225 per night
House ∙ 6 guests ∙ 2 bedrooms
5.0/5.0 "Excellent"
(73 ratings)
Hull, Plymouth County, Massachusetts
Free cancellation
Kitchen
Details
Vrbo
Details
House Kitchen Salisbury
e.g. 11/6 - 11/13 (Sat - Sat)
-58%
$205
$86 per night
House ∙ 2 guests ∙ 1 bedroom
4.7/5.0 "Outstanding"
(43 ratings)
Salisbury, Essex County, Massachusetts
Kitchen
Details
Vrbo
Details
House Kitchen Harwich Port
e.g. 12/26 - 1/2 (Sun - Sun)
$164 per night
House ∙ 4 guests ∙ 3 bedrooms
4.7/5.0 "Outstanding"
(23 ratings)
Harwich Port, Harwich, Massachusetts
Free cancellation
Kitchen
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Vrbo
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Cabins and Homes With Fireplaces

House Fireplace Dennis Port
e.g. 1/8 - 1/15 (Sat - Sat)
$205 per night
House ∙ 5 guests ∙ 2 bedrooms
5.0/5.0 "Excellent"
(133 ratings)
Dennis Port, Dennis, Massachusetts
Free cancellation
Fireplace
Details
Vrbo
Details
House Fireplace Yarmouth Port
e.g. 2/12 - 2/19 (Sat - Sat)
-27%
$415
$305 per night
House ∙ 8 guests ∙ 4 bedrooms
5.0/5.0 "Excellent"
(15 ratings)
Yarmouth Port, Yarmouth, Massachusetts
Free cancellation
Fireplace
Details
Vrbo
Details
Aparthotel Fireplace Falmouth
e.g. 12/18 - 12/25 (Sat - Sat)
$121 per night
Aparthotel ∙ 4 guests ∙ 1 bedroom
Falmouth, Barnstable County, Massachusetts
Fireplace
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HomeToGo
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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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