Massachusetts Vacation Rentals

Top Vacation Destinations in Massachusetts

  • Boston4,360 Properties
  • Nantucket3,276 Properties
  • Provincetown2,377 Properties
  • Eastham1,552 Properties
  • Dennis Port1,520 Properties
  • Brewster1,427 Properties
  • Chatham1,357 Properties
  • Wellfleet1,283 Properties
  • Orleans1,230 Properties

Our Favorite Vacation Rentals in Massachusetts

  • Tentrr - Birch Berry Pines
     Country House
    Booking.com
    From
    $86
  • ROOM walking distance to Mass MoCa
     Home/Apartment
    HolidayLettings
    From
    $137
  • Sweet Berkshire Getaway
     2br Home/Apartment
    HolidayLettings
    From
    $313
  • House On Main Street
     4br Home/Apartment
    HolidayLettings
    From
    $1,327
  • Retreat in the Woods
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $272
  • Golden Triangle in the Berkshires
    Nice2br Home/Apartment
    HolidayLettings
    From
    $3,140
  • Karin's Place
     7br Home/Apartment
    Flipkey
    From
    $1,868
  • Charming Berkshires lakefront house, great views
     2br Home/Apartment
    HolidayLettings
    From
    $348

Check prices for these upcoming dates

Massachusetts Vacation Rentals with a Pool

  • Hollywood Bungalow in Berkshires
    ExcellentHome/Apartment
    Airbnb
    From
    $209
  • 11-acre mid-century estate, newly renovated
    Excellent4br Home/Apartment
    Airbnb
    From
    $787
  • Getaway cabin for lovers
     Home/Apartment
    Airbnb
    From
    $1,085
  • Sunny S. Williamstown Loft with Stunning Views
    ExcellentStudio
    Airbnb
    From
    $147

Massachusetts Vacation Rentals with Wi-Fi

  • Bernie's & Betty's
    Excellent3br Home/Apartment
    Airbnb
    From
    $195
  • House near MassMoCA, full apartment
    Good2br Home/Apartment
    Airbnb
    From
    $71
  • Guest Apt. Near MCLA & MASS MoCA
    ExcellentHome/Apartment
    Airbnb
    From
    $102
  • Freemans Grove Benevolent Society Walk to MoCA
    Excellent2br Home/Apartment
    Airbnb
    From
    $220

Massachusetts Pet-Friendly Vacation Rentals

  • Apartment walking distance to Mass MoCa!!
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $233
  • 3 BR apartment, walking distance to Mass MoCa
     3br Home/Apartment
    HolidayLettings
    From
    $249
  • Walking distance to downtown
    Excellent2br Home/Apartment
    Airbnb
    From
    $161
  • Entire house just off Williams College campus.
    Excellent4br Home/Apartment
    Airbnb
    From
    $325

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.

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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    JazThe Life of a Social Butterfly
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Destinations in Massachusetts

  • Somerville1,142 Properties
  • Edgartown1,009 Properties
  • Cambridge1,000 Properties
  • West Yarmouth990 Properties
  • Falmouth956 Properties
  • Mashpee907 Properties
  • Hyannis903 Properties
  • Brookline872 Properties
  • Rockport796 Properties
  • South Yarmouth776 Properties
  • Tisbury769 Properties
  • Plymouth699 Properties
  • East Falmouth693 Properties
  • Gloucester659 Properties
  • South Chatham593 Properties
  • North Truro584 Properties
  • Lenox551 Properties
  • Dennis540 Properties
  • Harwich532 Properties
  • West Dennis529 Properties
  • Worcester517 Properties
  • Centerville499 Properties
  • Salem495 Properties
  • East Sandwich473 Properties
  • Harwich Port450 Properties
  • Waltham445 Properties
  • Great Barrington441 Properties
  • Hancock419 Properties
  • Lee416 Properties
  • Northampton397 Properties
  • Newton394 Properties
  • Vineyard Haven388 Properties
  • Revere376 Properties
  • Sandwich366 Properties
  • Medford360 Properties
  • Quincy355 Properties
  • Newburyport352 Properties
  • Williamstown350 Properties
  • Truro343 Properties
  • North Falmouth339 Properties
  • Watertown331 Properties
  • Pittsfield322 Properties
  • Marblehead312 Properties
  • Chelsea283 Properties
  • Amherst269 Properties
  • Stockbridge265 Properties
  • Marshfield262 Properties
  • South Dennis256 Properties
  • Arlington249 Properties
  • Barnstable236 Properties
  • Osterville234 Properties
  • Woburn227 Properties
  • Scituate217 Properties
  • West Harwich206 Properties
  • Wareham204 Properties
  • Sturbridge195 Properties
  • Bourne183 Properties
  • Chilmark175 Properties
  • Marlborough156 Properties
  • Fairhaven140 Properties
  • Winthrop132 Properties
  • Ipswich125 Properties
  • Westport122 Properties
  • West Stockbridge117 Properties
  • Hull117 Properties
  • Sheffield84 Properties
  • Manchester84 Properties
  • New Marlborough82 Properties
  • Concord82 Properties
  • Springfield67 Properties
  • Sudbury54 Properties
  • Ashburnham35 Properties
  • Cheshire27 Properties
  • Hubbardston8 Properties