Massachusetts Vacation Rentals

Top Vacation Destinations in Massachusetts

  • Boston3,434 Properties
  • Nantucket3,192 Properties
  • Provincetown2,229 Properties
  • Dennis Port1,609 Properties
  • Eastham1,543 Properties
  • Chatham1,430 Properties
  • Brewster1,338 Properties
  • Wellfleet1,243 Properties
  • Orleans1,173 Properties

Our Favorite Vacation Rentals in Massachusetts

  • ROOM walking distance to Mass MoCa
     Home/Apartment
    HolidayLettings
    From
    $137
  • Sweet Berkshire Getaway
     2br Home/Apartment
    HolidayLettings
    From
    $313
  • Getaways at the Patricia House
     4br Home/Apartment
    HolidayLettings
    From
    $243
  • 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
  • Sheeps Heaven View a stunning private suite in the Beautiful Berkshires
     3br Home/Apartment
    HolidayLettings
    From
    $208

Check prices for these upcoming dates

Massachusetts Vacation Rentals with a Pool

  • Hollywood Bungalow in Berkshires
    ExcellentHome/Apartment
    Airbnb
    From
    $197
  • 11-acre mid-century estate, newly renovated
    Excellent4br Home/Apartment
    Airbnb
    From
    $787
  • Ultra Luxury New Home in Berkshires (Williamstown)
     7br Home/Apartment
    Airbnb
    From
    $5,311
  • Berkshire Cottage for 4 near Jiminy Peak
    Good2br Home/Apartment
    Airbnb
    From
    $219

Massachusetts Vacation Rentals with Wi-Fi

  • House near MassMoCA, entire apartment
    Good2br Home/Apartment
    Airbnb
    From
    $64
  • Two Blocks to MoCA - Private & Cozy Garden Suite
    Excellent2br Home/Apartment
    Airbnb
    From
    $155
  • Freemans Grove Benevolent Society Walk to MoCA
    Excellent2br Home/Apartment
    Airbnb
    From
    $220
  • Tyler House in N Adams - walk to MASS MoCA
    Excellent3br Home/Apartment
    Airbnb
    From
    $136

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
  • Pollard Apartment in walking distance to Mass MoCA
    ExcellentHome/Apartment
    Airbnb
    From
    $101
  • Walking distance to downtown
    Excellent2br Home/Apartment
    Airbnb
    From
    $161

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.

What Expert Travelers Think

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    Monica
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  • — Packed full of information, from the best time of year to visit (I love NYC in Spring) to top tips from locals, All The Rooms provides the best accommodation, whether you are looking to enjoy your first time visit to New York or want to experience a new location

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    JazThe Life of a Social Butterfly
  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen

Destinations in Massachusetts

  • Somerville1,015 Properties
  • Edgartown983 Properties
  • West Yarmouth903 Properties
  • Cambridge865 Properties
  • Falmouth859 Properties
  • Mashpee841 Properties
  • Hyannis799 Properties
  • South Yarmouth766 Properties
  • Brookline747 Properties
  • Tisbury701 Properties
  • Plymouth667 Properties
  • Rockport656 Properties
  • East Falmouth654 Properties
  • West Dennis617 Properties
  • North Truro588 Properties
  • Gloucester577 Properties
  • South Chatham571 Properties
  • Lenox534 Properties
  • Harwich502 Properties
  • Worcester484 Properties
  • Salem462 Properties
  • Dennis460 Properties
  • Harwich Port441 Properties
  • East Sandwich438 Properties
  • Centerville433 Properties
  • Hancock429 Properties
  • Great Barrington404 Properties
  • Vineyard Haven396 Properties
  • Revere395 Properties
  • Waltham380 Properties
  • Lee359 Properties
  • Northampton354 Properties
  • Sandwich337 Properties
  • Quincy337 Properties
  • Truro335 Properties
  • Newton327 Properties
  • Medford320 Properties
  • Watertown318 Properties
  • Williamstown312 Properties
  • Newburyport305 Properties
  • Pittsfield297 Properties
  • Marblehead297 Properties
  • South Dennis284 Properties
  • North Falmouth265 Properties
  • Chelsea263 Properties
  • Amherst253 Properties
  • Marshfield242 Properties
  • Stockbridge242 Properties
  • Osterville229 Properties
  • Arlington229 Properties
  • Barnstable228 Properties
  • Wareham204 Properties
  • Scituate196 Properties
  • West Harwich193 Properties
  • Woburn185 Properties
  • Chilmark167 Properties
  • Bourne161 Properties
  • Sturbridge151 Properties
  • Fairhaven137 Properties
  • Winthrop127 Properties
  • Ipswich116 Properties
  • Westport115 Properties
  • West Stockbridge108 Properties
  • Marlborough107 Properties
  • Hull95 Properties
  • New Marlborough87 Properties
  • Sheffield80 Properties
  • Manchester75 Properties
  • Springfield64 Properties
  • Concord63 Properties
  • Sudbury48 Properties
  • Ashburnham33 Properties
  • Cheshire22 Properties
  • Hubbardston8 Properties