Massachusetts Vacation Rentals

Top Vacation Destinations in Massachusetts

  • Boston3,433 Properties
  • Nantucket3,179 Properties
  • Provincetown2,177 Properties
  • Eastham1,496 Properties
  • Dennis Port1,413 Properties
  • Chatham1,370 Properties
  • Brewster1,262 Properties
  • Wellfleet1,203 Properties
  • Orleans1,140 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
  • House On Main Street
     4br Home/Apartment
    HolidayLettings
    From
    $1,327
  • 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

Check prices for these upcoming dates

Massachusetts Vacation Rentals with a Pool

  • Hollywood Bungalow in Berkshires
    ExcellentHome/Apartment
    Airbnb
    From
    $153
  • 11-acre mid-century estate, newly renovated
    Good4br Home/Apartment
    Airbnb
    From
    $787
  • Ultra Luxury New Home in Williamstown
     6br Home/Apartment
    Airbnb
    From
    $5,283
  • Kid&Adult Festivals, Maple Syrup Farm Open House !
    Good2br Home/Apartment
    Airbnb
    From
    $201

Massachusetts Vacation Rentals with Wi-Fi

  • Bernie's & Betty's
    Excellent3br Home/Apartment
    Airbnb
    From
    $195
  • House near MassMoCA, entire apartment
    Good2br Home/Apartment
    Airbnb
    From
    $82
  • Two Blocks to MoCA - Private & Cozy Garden Suite
    Excellent2br Home/Apartment
    Airbnb
    From
    $147
  • 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
  • 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

Most expensive
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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

  • — I love All the Rooms because instead of having to check one place for home rentals, another for hotel, another for bed and breakfasts, and yet another for a room rental in a private residence, I can finally see EVERYTHING at one site; saving me considerable time

    Jeff Campbell
    Jeff CampbellMiddle Class Dad
  • — Site is easy to use; clean, laid out well, good colors and branding, fun logo and title that connects to the purpose of the brand. The blog, vacation destinations, and rental destinations is a great feature and really make the brand stand apart from other sites!

    Laurelle McVicker
    Laurelle McVickerLaurelle McVicker
  • — My favorite thing about AllTheRooms is that it combines both rentals and hotels available so you can see an entire view of what is available in a certain area. I was able to see listings on AllTheRooms that I never even saw on other travel sites!

    Daniella Flores
    Daniella FloresILIKETODABBLE

Destinations in Massachusetts

  • Somerville992 Properties
  • Edgartown954 Properties
  • West Yarmouth892 Properties
  • Cambridge861 Properties
  • Falmouth835 Properties
  • Mashpee814 Properties
  • Hyannis782 Properties
  • Brookline735 Properties
  • South Yarmouth721 Properties
  • Tisbury681 Properties
  • Plymouth648 Properties
  • Rockport641 Properties
  • East Falmouth629 Properties
  • North Truro572 Properties
  • Gloucester562 Properties
  • South Chatham551 Properties
  • Lenox523 Properties
  • West Dennis519 Properties
  • Harwich478 Properties
  • Worcester475 Properties
  • Salem458 Properties
  • Dennis442 Properties
  • Centerville427 Properties
  • East Sandwich423 Properties
  • Harwich Port418 Properties
  • Hancock412 Properties
  • Great Barrington396 Properties
  • Vineyard Haven379 Properties
  • Waltham375 Properties
  • Revere368 Properties
  • Lee353 Properties
  • Northampton352 Properties
  • Sandwich333 Properties
  • Quincy328 Properties
  • Truro326 Properties
  • Newton321 Properties
  • Watertown311 Properties
  • Williamstown307 Properties
  • Medford306 Properties
  • Newburyport299 Properties
  • Pittsfield293 Properties
  • Marblehead292 Properties
  • South Dennis257 Properties
  • Chelsea254 Properties
  • North Falmouth253 Properties
  • Amherst251 Properties
  • Marshfield239 Properties
  • Stockbridge233 Properties
  • Arlington225 Properties
  • Osterville220 Properties
  • Barnstable216 Properties
  • Wareham198 Properties
  • Scituate195 Properties
  • Woburn180 Properties
  • West Harwich178 Properties
  • Chilmark163 Properties
  • Bourne156 Properties
  • Sturbridge150 Properties
  • Fairhaven133 Properties
  • Winthrop125 Properties
  • Ipswich112 Properties
  • Westport110 Properties
  • West Stockbridge107 Properties
  • Marlborough106 Properties
  • Hull95 Properties
  • New Marlborough80 Properties
  • Sheffield75 Properties
  • Manchester74 Properties
  • Springfield64 Properties
  • Concord63 Properties
  • Sudbury47 Properties
  • Ashburnham33 Properties
  • Cheshire21 Properties
  • Hubbardston7 Properties