Massachusetts vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

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
Aug 13 – 20
$352 per night
4.94 out of 5 average rating, 345 reviews
Guest favorite
Guesthouse in Barnstable
Modern Fireplaced Carriage House with Beach Permit
Feel at home & relax in our new one bedroom carriage house. Modern yet classic Cape Cod style and elegance. Rest easy on a new Stearns & Foster king size mattress with designer linens and furnishings. Cozy up to the fireplace and flat screen TV. Custom bathroom, Bosch laundry units and small deck. Kitchenette with dishwasher drawer, under cabinet refrigeration, microwave, toaster, Keurig coffee maker, Starbucks coffee and various teas. We offer beach chairs, bags & towels for your convenience.
Mar 27 – Apr 3
$298 per night
5.0 out of 5 average rating, 110 reviews
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.
Sep 8 – 15
$123 per night
4.99 out of 5 average rating, 144 reviews

Popular amenities for Massachusetts vacation rentals

Massachusetts waterfront vacation rentals

Guest favorite
Guest suite in Tyngsborough
Lakefront Suite Two-Room, Comfy, Tranquil
May 10 – 17
$109 per night
4.98 out of 5 average rating, 215 reviews
Guest favorite
Cottage in Sandwich
Waterfront Lake Cottage, Private Beach, Wow View!
Oct 24 – 31
$330 per night
4.95 out of 5 average rating, 152 reviews
Guest favorite
Cottage in Plymouth
Stunning ocean views, stairs down to the beach
Feb 12 – 19
$420 per night
4.96 out of 5 average rating, 160 reviews
Guest favorite
Cottage in Becket
Cozy lakeside cottage
Dec 2 – 9
$183 per night
4.95 out of 5 average rating, 121 reviews
Guest favorite
Cottage in Sandwich
Oceanfront & Pet Friendly Cottage ~ Lil’ Sea Sass
Nov 16 – 23
$399 per night
4.88 out of 5 average rating, 297 reviews
Guest favorite
Apartment in Salem
Historic Salem Oceanfront 2 Rm Apt
Mar 28 – Apr 4
$159 per night
4.95 out of 5 average rating, 600 reviews
Guest favorite
Cottage in Plymouth
Ocean View Cottage
Nov 12 – 17
$150 per night
4.93 out of 5 average rating, 222 reviews
Guest favorite
Loft in Rockport
Loft Apartment With Ocean Views
Apr 8 – 15
$238 per night
4.98 out of 5 average rating, 239 reviews
Guest favorite
Cottage in Yarmouth
Cozy Coastal Cottage With Sprawling Sea Views
Oct 4 – 11
$161 per night
4.95 out of 5 average rating, 177 reviews
Guest favorite
Guest suite in Marblehead
Ocean Park Retreat
Dec 23 – 30
$99 per night
4.92 out of 5 average rating, 243 reviews
Guest favorite
Loft in Rockport
Chic Downtown Loft ☆ Private Parking ☆ Ocean View
Nov 29 – Dec 6
$137 per night
5.0 out of 5 average rating, 192 reviews
Guest favorite
Cottage in Swansea
Romantic Beach Cottage Getaway - Swansea MA
Dec 2 – 9
$237 per night
4.93 out of 5 average rating, 162 reviews

Massachusetts fishing vacation rentals

Guest favorite
Cottage in Sturbridge
Cozy Cottage on Cedar Lake- "Cottage Cheeze"
Apr 28 – May 5
$221 per night
4.93 out of 5 average rating, 121 reviews
Guest favorite
Home in Sturbridge
Lake Front Home Sleeps 6-8 on a private Peninsula!
Nov 7 – 14
$288 per night
4.94 out of 5 average rating, 205 reviews
Guest favorite
Guest suite in Charlton
Baker Pond Hideaway
Jan 3 – 10
$104 per night
4.86 out of 5 average rating, 378 reviews
Guest favorite
Guest suite in Chatham
Waterfront Suite on Emery Pond
Aug 25 – Sep 1
$226 per night
4.99 out of 5 average rating, 203 reviews
Superhost
Cottage in Wareham
Onset beach, Cape code.Private Waterfront cottage
Apr 15 – 22
$169 per night
4.85 out of 5 average rating, 115 reviews
Superhost
Home in Winchendon
Waterfront home 2 bedrooms withdeck beach and dock
May 31 – Jun 7
$130 per night
4.8 out of 5 average rating, 134 reviews
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
Cottage in Ashfield
hope house
Oct 26 – Nov 2
$145 per night
4.97 out of 5 average rating, 296 reviews
Guest favorite
Home in Brimfield
Brimfield Lakeside Home Away from Home
Jun 6 – 13
$195 per night
4.93 out of 5 average rating, 137 reviews
Guest favorite
Home in Dennis
Lakefront House/Private Dock/Year Round Hot Tub/AC
Jan 30 – Feb 6
$216 per night
4.95 out of 5 average rating, 147 reviews
Guest favorite
Home in Norton
THE RED HOUSE - Entire Private Home
Jun 1 – 8
$121 per night
4.9 out of 5 average rating, 172 reviews
Guest favorite
Home in Southwick
Linny's Lakeview Cottage
May 11 – 18
$162 per night
4.99 out of 5 average rating, 175 reviews

Massachusetts home rentals

Guest favorite
Home in Middleborough
Private retreat setting on 4 acres 1
Feb 10 – 17
$88 per night
4.94 out of 5 average rating, 293 reviews
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 Plymouth
Panoramic ocean views 100 ft above Cape Cod Bay
Dec 17 – 24
$678 per night
4.93 out of 5 average rating, 104 reviews
Guest favorite
Home in Falmouth
Mid-Century Modern home 5 minute walk to beach
Apr 20 – 27
$377 per night
4.97 out of 5 average rating, 105 reviews
Guest favorite
Home in Barnstable
Cape Cod Cotuit Cottage, 3 Bed Near Beaches
Dec 9 – 16
$200 per night
5.0 out of 5 average rating, 104 reviews
Guest favorite
Home in Chester
Riverfront Getaway
Nov 11 – 18
$159 per night
4.96 out of 5 average rating, 305 reviews
Guest favorite
Home in Framingham
1BR—Bright & Cozy 2-Level Home — 25 Min to Boston
Apr 2 – 9
$136 per night
4.89 out of 5 average rating, 246 reviews
Guest favorite
Home in Sandwich
Steps to Cape Cod Private Beach!
Sep 22 – 29
$196 per night
4.89 out of 5 average rating, 112 reviews
Guest favorite
Home in Dedham
The Gatehouse, Cheerful 3 bedroom 3 bathroom house
Oct 23 – 30
$413 per night
5.0 out of 5 average rating, 141 reviews
Guest favorite
Home in Lynn
Clean, spacious In-Law Suite -Near Everything
Dec 4 – 11
$127 per night
4.91 out of 5 average rating, 225 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 Ipswich
Stagehill Beach House
Apr 19 – 26
$436 per night
4.98 out of 5 average rating, 170 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