Find Vacation Rentals in Massachusetts

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Massachusetts

Popular Massachusetts Vacation Homes and Apartments

Find the perfect Massachusetts vacation rental

House ∙ 4 guests ∙ 2 bedrooms
Plymouth, Plymouth County, Massachusetts
from $117
VRBO
5.0
Details
Apartment ∙ 2 guests ∙ 1 bedroom
Lee, Berkshire County, Massachusetts
from $65
VRBO
4.7
Details
Apartment ∙ 4 guests ∙ 2 bedrooms
Provincetown, Barnstable County, Massachusetts
from $54
VRBO
5.0
Details
Apartment ∙ 4 guests ∙ 2 bedrooms
Greenfield, Franklin County, Massachusetts
from $51
Airbnb
5.0
Details
Apartment ∙ 4 guests ∙ 1 bedroom
Orleans, Orleans Town, Massachusetts
from $54
Airbnb
5.0
Details
Apartment ∙ 3 guests ∙ 1 bedroom
Great Barrington, Berkshire County, Massachusetts
from $54
Airbnb
5.0
Details
Apartment ∙ 4 guests ∙ 2 bedrooms
Adams, Berkshire County, Massachusetts
from $113
Airbnb
5.0
Details
Apartment ∙ 5 guests ∙ 2 bedrooms
Housatonic, Great Barrington, Massachusetts
from $61
Airbnb
4.5
Details
Apartment ∙ 2 guests ∙ 1 bedroom
Littleton, Middlesex County, Massachusetts
from $54
Airbnb
5.0
Details
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Vacation Properties for Fishing

Fishing
Apartment ∙ 2 guests ∙ 1 bedroom
Gloucester, Essex County, Massachusetts
from $53
VRBO
5.0
Details
Fishing
Apartment ∙ 3 guests ∙ 1 bedroom
Harbor View / Orient Heights, Boston, Massachusetts
from $54
VRBO
4.5
Details
Fishing
Apartment ∙ 2 guests ∙ 1 bedroom
Brook Farm, Boston, Massachusetts
from $54
VRBO
4.9
Details
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Cabins and Homes With Fireplaces

Fireplace
Apartment ∙ 3 guests ∙ 1 bedroom
Dennis Port, Dennis, Massachusetts
from $123
VRBO
4.8
Details
Fireplace
Apartment ∙ 4 guests ∙ 1 bedroom
Pepperell, Middlesex County, Massachusetts
from $51
VRBO
5.0
Details
Fireplace
House ∙ 6 guests ∙ 3 bedrooms
East Sandwich, Sandwich, Massachusetts
from $231
VRBO
5.0
Details
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Vacation Homes With Terraces

Balcony/Patio
Apartment ∙ 4 guests ∙ 2 bedrooms
Plymouth Cultural District, North Plymouth, Massachusetts
from $66
VRBO
4.8
Details
Balcony/Patio
House ∙ 8 guests ∙ 3 bedrooms
Salisbury, Essex County, Massachusetts
from $232
VRBO
5.0
Details
Balcony/Patio
House ∙ 8 guests ∙ 3 bedrooms
Green Harbor-Cedar Crest, Marshfield, Massachusetts
from $229
VRBO
5.0
Details
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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!

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

Looking for a vacation rental in Massachusetts? Tripping.com has 42392 vacation rental homes available in Massachusetts. You'll find 370 studios, 10358 1-bedroom, 7579 2-bedroom and 24085 rentals with 3 or more bedrooms ranging from €25 a night. For extra convenience, many of these vacation homes can be booked directly online.

The average price of a nightly rental in Massachusetts is €400 while the average price of a weekly rental is €2861. For those looking for more than a short term rental such as corporate rentals, extended stays or long term rentals, the average monthly price of a Massachusetts home is €10938.

Wondering if you can bring your dog or cat along with you? There are 8826 pet-friendly vacation rentals available in Massachusetts. In addition to accommodating pets, Massachusetts rentals offer a variety of amenities. In particular, 36284 rentals have Internet and WiFi, 36842 have TV and/or cable and 4799 have a pool or hot tub.

Search properties from 16 vacation rental sites in Massachusetts where the top providers in that area are HomeAway, TripAdvisor, and Booking.com. There are 22423 HomeAway rentals, 9474 TripAdvisor short term rentals and 2917 Booking.com vacation rentals.

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