Massachusetts Vacation Rentals

Top Vacation Destinations in Massachusetts

  • Boston4,376 Properties
  • Nantucket3,380 Properties
  • Provincetown2,433 Properties
  • Eastham1,596 Properties
  • Dennis Port1,559 Properties
  • Brewster1,489 Properties
  • Chatham1,424 Properties
  • Wellfleet1,322 Properties
  • Orleans1,254 Properties

Our Favorite Vacation Rentals in Massachusetts

  • Meadowhurst Farm
     Family Stay
    Booking.com
    From
    $78
  • Bernie's & Betty's
    Excellent3br Home/Apartment
    Airbnb
    From
    $195
  • House near MassMoCA, entire apartment
    Good2br Home/Apartment
    Airbnb
    From
    $68
  • Two Blocks to MoCA - Private & Cozy Garden Suite
    Excellent2br Home/Apartment
    Airbnb
    From
    $130
  • 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
    $147
  • Berkshire Guest Suite
    ExcellentHome/Apartment
    Airbnb
    From
    $73
  • Private home in quaint, quiet neighborhood
    Excellent2br Home/Apartment
    Airbnb
    From
    $147

Check prices for these upcoming dates

Massachusetts Vacation Rentals with a Pool

  • Hollywood Bungalow in Berkshires
    ExcellentHome/Apartment
    Airbnb
    From
    $154
  • 11-acre mid-century estate, newly renovated
    Good4br Home/Apartment
    Airbnb
    From
    $787
  • Berkshire Cottage for 4 near Jiminy Peak
    Good2br Home/Apartment
    Airbnb
    From
    $219
  • Karin's Place: A Secluded Retreat
    Excellent9br Home/Apartment
    Airbnb
    From
    $1,610

Massachusetts Vacation Rentals with Wi-Fi

  • Three Sisters
    Good2br Home/Apartment
    Airbnb
    From
    $102
  • Pollard Apartment in walking distance to Mass MoCA
    ExcellentHome/Apartment
    Airbnb
    From
    $101
  • Cozy barn apartment on the river
    ExcellentHome/Apartment
    Airbnb
    From
    $153
  • Walking distance to downtown
    Excellent2br Home/Apartment
    Airbnb
    From
    $161

Massachusetts Pet-Friendly Vacation Rentals

  • Entire house just off Williams College campus.
    Excellent4br Home/Apartment
    Airbnb
    From
    $325
  • Charming Williamstown Cape
    Excellent3br Home/Apartment
    Airbnb
    From
    $297
  • Cozy in-town bungalow.
    Excellent2br Home/Apartment
    Airbnb
    From
    $158
  • 4 bedroom charming Colonial near dtwn Williamstown
    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.

What Expert Travelers Think

  • — I travel to Boston regularly and I like to use AllTheRooms as it’s tricky to find good accommodation at a good price. The platform is easy to use and provides a complete set of features that saves me time and money on every trip

    Clwyd Probert
    Clwyd ProbertWhitehat
  • — When I plan a trip, I no longer waste time visiting multiple websites in search of the best accommodations. Now, I just go to AllTheRooms and immediately find everything from luxury villas to pet-friendly rentals! All in one place

    Whitney Wear
    Whitney WearTravel Better Guide
  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston

Destinations in Massachusetts

  • Somerville1,180 Properties
  • Edgartown1,037 Properties
  • Cambridge1,017 Properties
  • West Yarmouth1,012 Properties
  • Falmouth976 Properties
  • Mashpee925 Properties
  • Hyannis922 Properties
  • Brookline919 Properties
  • Rockport816 Properties
  • South Yarmouth796 Properties
  • Tisbury777 Properties
  • Plymouth723 Properties
  • East Falmouth710 Properties
  • Gloucester683 Properties
  • South Chatham610 Properties
  • North Truro598 Properties
  • Lenox582 Properties
  • West Dennis563 Properties
  • Harwich557 Properties
  • Dennis546 Properties
  • Worcester538 Properties
  • Centerville512 Properties
  • Salem508 Properties
  • East Sandwich479 Properties
  • Harwich Port477 Properties
  • Waltham462 Properties
  • Great Barrington456 Properties
  • Hancock454 Properties
  • Lee426 Properties
  • Newton407 Properties
  • Revere401 Properties
  • Northampton400 Properties
  • Vineyard Haven399 Properties
  • Sandwich375 Properties
  • Medford374 Properties
  • Quincy368 Properties
  • Williamstown358 Properties
  • Newburyport355 Properties
  • Watertown351 Properties
  • Truro350 Properties
  • North Falmouth341 Properties
  • Pittsfield334 Properties
  • Marblehead322 Properties
  • Chelsea301 Properties
  • South Dennis277 Properties
  • Amherst273 Properties
  • Stockbridge272 Properties
  • Marshfield267 Properties
  • Arlington254 Properties
  • Barnstable242 Properties
  • Osterville240 Properties
  • Woburn231 Properties
  • Scituate221 Properties
  • West Harwich210 Properties
  • Wareham209 Properties
  • Sturbridge197 Properties
  • Bourne185 Properties
  • Chilmark182 Properties
  • Marlborough161 Properties
  • Fairhaven144 Properties
  • Winthrop138 Properties
  • Ipswich127 Properties
  • Westport124 Properties
  • West Stockbridge121 Properties
  • Hull117 Properties
  • Concord88 Properties
  • Manchester88 Properties
  • Sheffield88 Properties
  • New Marlborough85 Properties
  • Springfield67 Properties
  • Sudbury57 Properties
  • Ashburnham36 Properties
  • Cheshire29 Properties
  • Hubbardston8 Properties