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.

Superhost
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 24 – 29
$95 per night
4.88 out of 5 average rating, 284 reviews
Guest favorite
Guest suite in Tyngsborough
Lakefront Suite Two-Room, Comfy, Tranquil
Re-opening mid April! Guests can enjoy a lovely small lake with a panoramic view, a spa-like bathroom, cotton linens, and a comfy bed. A/C and a fireplaced living room. Quietly watch lake nature or boats going by, venture out to swim, kayak, or fish. Enjoy Lowell's mill history and it's national park, take a forest walk nearby, or drive 10 min. to Nashua, NH for its many restaurants and tax-free shopping. One hour from Boston and central to New England highlights. Low cleaning fees too!
Sep 7 – 14
$109 per night
4.98 out of 5 average rating, 215 reviews
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
Nov 15 – 22
$352 per night
4.94 out of 5 average rating, 345 reviews

Popular amenities for Massachusetts vacation rentals

Massachusetts waterfront vacation rentals

Guest favorite
Cottage in Plymouth
Ocean View Cottage
Jan 20 – 25
$150 per night
4.93 out of 5 average rating, 222 reviews
Guest favorite
Guest suite in Marblehead
Ocean Park Retreat
Dec 28 – Jan 4
$106 per night
4.92 out of 5 average rating, 243 reviews
Guest favorite
Guest suite in Charlton
Baker Pond Hideaway
Nov 13 – 20
$104 per night
4.86 out of 5 average rating, 378 reviews
Guest favorite
Loft in Gloucester
Rocky Neck Studio/Loft, Gloucester, Mass.
May 8 – 15
$96 per night
4.9 out of 5 average rating, 167 reviews
Guest favorite
Guest suite in Orleans
Charming Old Cape Cod
Mar 23 – 30
$113 per night
4.91 out of 5 average rating, 141 reviews
Guest favorite
Cabin in Littleton
Private & Remote, Enjoy Outdoors, Sleep in Luxury
May 6 – 13
$153 per night
4.98 out of 5 average rating, 113 reviews
Guest favorite
Guest suite in Gloucester
SplashLanding Private Beach Getaway in Gloucester
Jun 5 – 12
$295 per night
4.98 out of 5 average rating, 374 reviews
Guest favorite
Cottage in Plymouth
Stunning ocean views, stairs down to the beach
Feb 13 – 20
$420 per night
4.96 out of 5 average rating, 160 reviews
Guest favorite
Cottage in Sandwich
Waterfront Lake Cottage, Private Beach, Wow View!
Oct 25 – Nov 1
$330 per night
4.95 out of 5 average rating, 152 reviews
Superhost
Home in Plymouth
OCEANFRONT Home on secluded beach.
Oct 25 – Nov 1
$468 per night
4.88 out of 5 average rating, 144 reviews
Guest favorite
Apartment in Salem
Historic Salem Oceanfront 2 Rm Apt
May 5 – 10
$175 per night
4.95 out of 5 average rating, 600 reviews
Superhost
Home in Winchendon
Waterfront home 2 bedrooms withdeck beach and dock
May 2 – 9
$130 per night
4.8 out of 5 average rating, 134 reviews

Massachusetts fishing vacation rentals

Guest favorite
Cottage in Eastham
Barn Cottage on Minister Pond
Sep 29 – Oct 6
$125 per night
4.9 out of 5 average rating, 342 reviews
Guest favorite
Home in Norton
THE RED HOUSE - Entire Private Home
May 22 – 29
$121 per night
4.9 out of 5 average rating, 172 reviews
Guest favorite
Apartment in Natick
Scandi-Modern Apartment
Sep 4 – 11
$111 per night
4.98 out of 5 average rating, 330 reviews
Guest favorite
Apartment in Great Barrington
Private En Suite in Beautiful Victorian
Feb 15 – 22
$96 per night
4.95 out of 5 average rating, 313 reviews
Guest favorite
Cottage in Ashfield
hope house
Oct 27 – Nov 3
$145 per night
4.97 out of 5 average rating, 296 reviews
Guest favorite
Home in Southwick
Linny's Lakeview Cottage
May 11 – 18
$145 per night
4.99 out of 5 average rating, 177 reviews
Guest favorite
Cottage in Eastham
The Breeze Overlooking Minister's Pond
Apr 20 – 27
$168 per night
4.95 out of 5 average rating, 204 reviews
Guest favorite
Home in Monterey
Charming cottage w/ gorgeous views.
Feb 17 – 24
$145 per night
4.92 out of 5 average rating, 306 reviews
Guest favorite
Home in Sturbridge
Lake Front Home Sleeps 6-8 on a private Peninsula!
Nov 29 – Dec 6
$288 per night
4.94 out of 5 average rating, 207 reviews
Guest favorite
Cottage in Becket
BERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.
May 8 – 15
$161 per night
4.94 out of 5 average rating, 236 reviews
Guest favorite
Home in Leicester
Cozy Lake House
Oct 24 – 31
$193 per night
4.94 out of 5 average rating, 104 reviews
Guest favorite
Guest suite in Sharon
Cozy Lakeview Guesthouse
Feb 9 – 16
$152 per night
4.97 out of 5 average rating, 141 reviews

Massachusetts home rentals

Guest favorite
Home in Plymouth
Romantic Get-Away or Fun filled Family Vacation
Nov 8 – 15
$111 per night
4.94 out of 5 average rating, 109 reviews
Guest favorite
Home in Middleborough
Private retreat setting on 4 acres 1
Mar 22 – 29
$88 per night
4.94 out of 5 average rating, 293 reviews
Guest favorite
Home in Chester
Riverfront Getaway
Dec 9 – 16
$159 per night
4.96 out of 5 average rating, 307 reviews
Guest favorite
Home in Lynn
Clean, spacious In-Law Suite -Near Everything
Jan 10 – 17
$127 per night
4.91 out of 5 average rating, 225 reviews
Superhost
Home in Revere
Renovated Cozy City Getaway
Feb 18 – 25
$85 per night
4.79 out of 5 average rating, 135 reviews
Guest favorite
Home in Quincy
Artist's Haven (2)
Mar 26 – Apr 2
$100 per night
4.96 out of 5 average rating, 121 reviews
Guest favorite
Home in Ware
Little House Inn
Dec 25 – Jan 1
$135 per night
4.88 out of 5 average rating, 102 reviews
Guest favorite
Home in Williamsburg
Hilltown Studio
Nov 30 – Dec 7
$108 per night
4.99 out of 5 average rating, 155 reviews
Guest favorite
Home in Billerica
Residential home ▪ Billerica ▪ quiet, clean & cozy
Dec 22 – 29
$133 per night
4.97 out of 5 average rating, 148 reviews
Guest favorite
Home in Feeding Hills
Farm Fresh Feeding Hills
Apr 24 – May 1
$99 per night
4.89 out of 5 average rating, 872 reviews
Guest favorite
Home in Barnstable
Cape Cod Cotuit Cottage, 3 Bed Near Beaches
Feb 10 – 17
$160 per night
5.0 out of 5 average rating, 104 reviews
Guest favorite
Home in Plymouth
Panoramic ocean views 100 ft above Cape Cod Bay
Oct 7 – 14
$852 per night
4.93 out of 5 average rating, 106 reviews

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