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Massachusetts vacation rentals

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Top-rated vacation rentals in Massachusetts

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite
Chalet in Otis
Mid-Century Glass Octagon in the Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon
Feb 14 – 21
$352 per night
Farm stay in Southbridge
Scandanavian Wigwam with Sauna and Forest Baths
Deep sleeps await in our off grid forest Wigam. With everything you need, and nothing you do not, this exceptional retreat boasts a Danish Morso wood stove, fire pit, private forest baths, Finnish sauna, HUGE windows overlooking a wildlife trail and Peepers Owls and Coyote song. From photo shoots to wedding proposals - this is a special place to care for yourself and your family. We are on farm - but out of sight. Bring your kids, dogs, friends, guitar, or just a good book and settle in!
Mar 16 – 21
$99 per night
Guest favorite
Cottage in Petersham
Cider House Cottage
Antique guest cottage on a country farm property with acres of fields, ponds, forests and streams, adjoining Quabbin Reservoir domain. Ideal for hikers, bird watchers, and bicyclists, this quiet country retreat offers trails and terrain to explore, only 3 miles away from small historic New England town. Make yourself at home in the comfortably furnished post and beam home with terrace and pond views, adventure in the surroundings, dip in fresh water streams, and relax in the claw foot bathtub.
Jun 17 – 24
$127 per night

Popular amenities for Massachusetts vacation rentals

Massachusetts home rentals

Guest favorite
Home in Middleborough
Private retreat setting on 4 acres 1
Feb 10 – 17
$88 per night
Guest favorite
Home in Plymouth
Romantic Get-Away or Fun filled Family Vacation
Feb 15 – 22
$110 per night
Guest favorite
Home in Sandwich
Steps to Cape Cod Private Beach!
Sep 27 – Oct 4
$179 per night
Guest favorite
Home in Lee
Berkshire Mountain retreat with Urban eco-luxuries
Apr 14 – 21
$276 per night
Home in Revere
Renovated Cozy City Getaway
Aug 21 – 28
$86 per night
Guest favorite
Home in Westport
Mermaid Cottage
Mar 4 – 11
$113 per night
Guest favorite
Home in Falmouth
The Driftwood Home, 5 min from Mashpee Commons, AC
Jul 7 – 14
$498 per night
Guest favorite
Home in Plymouth
Panoramic ocean views 100 ft above Cape Cod Bay
Nov 8 – 15
$684 per night
Guest favorite
Home in Sandwich
Quintessential Waterfront Historic Cottage
Mar 6 – 13
$495 per night
Guest favorite
Home in Westminster
Lakefront; view of ski mtn, firepit, dock, kayaks
Dec 19 – 26
$278 per night
Guest favorite
Home in Mattapoisett
*Cozy Escape* Historic South Coast Retreat
May 24 – 31
$152 per night
Guest favorite
Home in Framingham
*Stay Tonight* Brookside Loft—Quiet & Clean 1BR
Mar 9 – 16
$124 per night

Other great vacation rentals in Massachusetts

Guest favorite
Cottage in Orange
The Lake Cottage: A Sweetwater Stay
Dec 24 – 31
$104 per night
Guest favorite
Cabin in North Adams
Mahican Cabin - A Private Nature's Reserve For 2
Jul 28 – Aug 4
$246 per night
Guest favorite
Barn in Holden
Farm stay in a Historic Ski Lodge turned Barn
May 16 – 23
$142 per night
Guest favorite
Treehouse in Tyringham
Gingerbread House Tower in the Berkshire Hills
Jun 3 – 10
$268 per night
Guest favorite
Guesthouse in Uxbridge
Zen Inspired Private Suite with 2-mile Trail Loop
Aug 22 – 29
$141 per night
Guest favorite
Loft in Swampscott
Gorgeous Oceanfront Penthouse
May 29 – Jun 5
$263 per night
Guest favorite
Cottage in Plymouth
Stunning ocean views, stairs down to the beach
Sep 22 – 29
$350 per night
Guest favorite
Cabin in Cohasset
Lionsgate at Cohasset
Mar 9 – 16
$94 per night
Guest favorite
Guest suite in Uxbridge
Beautiful, Unique, & Cozy Cedar Flat
Aug 19 – 26
$120 per night
Guest favorite
Guesthouse in Barnstable
Modern Fireplaced Carriage House with Beach Permit
May 2 – 9
$298 per night
Guest favorite
Cottage in Sandwich
Waterfront Lake Cottage, Private Beach, Wow View!
Feb 15 – 22
$331 per night
Guest favorite
Cottage in Sandwich
Lil’ Sea Sass ~ Oceanfront Cottage & Pet Friendly
Jun 6 – 13
$799 per night

Your guide to Massachusetts

All About Massachusetts

Massachusetts’ bustling capital, Boston, draws in travelers seeking to explore the city’s extensive history, legendary baseball stadium, and impressive arts scene — but this northeastern state offers varied geography and options beyond its biggest city. There are opportunities for outdoor adventure, rest and relaxation, and arts and culture throughout the state. Western Massachusetts and the Berkshires is the state's rural mountain region popular with ski resorts and snow-shoeing for outdoor athletes. The towns and many farms of the central region host fall harvest celebrations and farm-to-table dining with some of the state’s best fall foliage driving routes.

Sturbridge Village is ideal for history buffs wanting a glimpse into life in New England during the 19th century. Cape Cod, a hook-shaped peninsula abou 70 miles south of Boston, is known for its beautiful beaches and lighthouses. Beachgoers and island lovers can take a ferry to the islands of Nantucket and Martha’s Vineyard for swimming, surfing, and miles of bike trails. The state’s rich maritime tradition is evident in the northern coastal towns of Newburyport, Rockport, and Marblehead.

Boston is rich in history and culture — dine at one of its award-winning restaurants or make your way through the Freedom Trail, which weaves through the city passing iconic sites of the American Revolution and gorgeous green spaces like Boston Commons and Public Garden.

The best time to stay in a vacation rental in Massachusetts

Fall is an excellent time for a trip to the state, bringing bright, colorful foliage and the chance to meander down the scenic Route 2 highway from Boston to western Massachusetts. There are hot, humid summers and snowy, cold winters here, weather typical for most northeastern states. Summers also come with intense thunderstorms, but that doesn’t stop people from enjoying the beaches or heading to the Berkshires for Tanglewood’s summer music lineup.

Massachusetts is susceptible to hurricanes from June until November, though the majority weaken to tropical storms as they pass by the state. Winters are milder along the coast, with temperatures staying above freezing even in January. As you move further inland, it gets colder, and snowfall in the mountains is perfect for skiing and snowshoeing. Spring is generally wet and cloudy across the state, but let that stop you from exploring the Brimfield Antique Show, the largest antiques show in the country.

Top things to do in Massachusetts

Explore the History of Lexington

Drive 20 minutes outside Boston to the birthplace of the Revolutionary War. Hop on the Liberty Ride Trolley and pass multiple pivotal historical sites. Favorite stops include Lexington Battle Green — where the first shot of the Revolutionary War was fired in 1775 — and significant literary sites from classic American writers.

The Berkshires

Located on the far western border of the state, The Berkshires are popular with outdoor enthusiasts, artists, shoppers, and foodies. Known for the mountains and ski resorts here, it's a winter wonderland for skiers, snowboarders, and even offers snow tubing. Once the snow melts, you’ll find epic hiking trails, white-water rafting, and climbing opportunities abound. Towns throughout the area including Lenox, Great Barrington, Stockbridge, offer farm-to-table restaurants, antique shopping, unique musical experiences, and local theatres.

Western Massachusetts wineries

Explore picturesque vineyards while sipping on award-winning wines from dozens of wineries across Western Massachusetts. A rising star on the global wine stage, the area's wines are hand-crafted from a variety of grapes, fruits, berries, and even flowers. The region’s most common grape varieties are the vinifera varieties including chardonnay, pinot grigio, riesling, and pinot noir. Many of the wineries can be found between Amherst and Springfield with stunning landscapes to enjoy along the way.

Destinations to explore