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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Massachusetts vacation rentals
Other great vacation rentals in Massachusetts
Home in Plymouth
4.92 out of 5 average rating, 111 reviewsRomantic Get-Away or Fun filled Family Vacation
Dec 23 – 30
Home in Southwick
4.99 out of 5 average rating, 181 reviewsLinny's Lakeview Cottage
Dec 3 – 10
Home in Revere
4.79 out of 5 average rating, 139 reviewsRenovated Cozy City Getaway
Jan 20 – 27
Home in North Truro
4.98 out of 5 average rating, 264 reviewsBeautiful North Truro cottage with screen porch
Jan 27 – Feb 3
Home in Middleborough
4.94 out of 5 average rating, 295 reviewsPrivate retreat setting on 4 acres 1
Apr 19 – 26
Home in Lynn
4.91 out of 5 average rating, 226 reviewsClean, spacious In-Law Suite -Near Everything
Feb 16 – 23
Home in Norton
4.9 out of 5 average rating, 174 reviewsTHE RED HOUSE - Entire Private Home
Sep 12 – 19
Home in Quincy
4.96 out of 5 average rating, 124 reviewsArtist's Haven (2)
Jun 20 – 27
Other great vacation rentals in Massachusetts
Guesthouse in Framingham
4.98 out of 5 average rating, 201 reviewsPrivate guest house on beautiful country road
Mar 17 – 24
Guest suite in Stoughton
4.99 out of 5 average rating, 160 reviewsModern private studio with outdoor hot tub!
Aug 11 – 18
Guesthouse in Uxbridge
5.0 out of 5 average rating, 123 reviewsZen Inspired Private Suite with 2-mile Trail Loop
Aug 27 – Sep 3
Apartment in Ipswich
4.96 out of 5 average rating, 108 reviewsCozy Wade Carriage House Studio
Jan 10 – 17
Guest suite in Littleton
4.91 out of 5 average rating, 315 reviewsHistoric Loft with bathroom & kitchenette
Aug 8 – 15
Chalet in Otis
4.94 out of 5 average rating, 349 reviewsMid-Century Glass Octagon in the Berkshires
Dec 9 – 16
Apartment in Barnstable
4.99 out of 5 average rating, 231 reviewsYour dog will love it here and you will too.
Feb 19 – 26
Guesthouse in Falmouth
4.9 out of 5 average rating, 235 reviewsWooded studio apartment in Woods Hole village
Mar 2 – 9
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
- Smoking-friendly rentals Massachusetts
- Wheelchair accessible rentals Massachusetts
- Rentals with an EV charger Massachusetts
- House rentals Massachusetts
- Apartment rentals Massachusetts
- Rentals with outdoor seating Massachusetts
- Rentals with an accessible height toilet Massachusetts
- Waterfront rentals Massachusetts
- Monthly Rentals Massachusetts
- Rentals with a patio Massachusetts
- Rentals with a sauna Massachusetts
- Luxury rentals Massachusetts
- Chalet rentals Massachusetts
- Townhouse rentals Massachusetts
- Rentals with a washer and dryer Massachusetts
- Rentals with a hot tub Massachusetts
- Rentals with beach access Massachusetts
- Hotel rentals Massachusetts
- Family-friendly rentals Massachusetts
- Rentals with a home theater Massachusetts
- Rentals with pools Massachusetts
- Loft rentals Massachusetts
- Farmstay rentals Massachusetts
- Villa rentals Massachusetts
- Condo rentals Massachusetts
- Rentals with an accessible height bed Massachusetts
- Lakehouse rentals Massachusetts
- Barn rentals Massachusetts
- Bungalow rentals Massachusetts
- Rentals with lake access Massachusetts
- Rentals with a kayak Massachusetts
- Cabin rentals Massachusetts
- Tiny house rentals Massachusetts
- Fitness-friendly rentals Massachusetts
- Rentals with a fireplace Massachusetts
- Resort rentals Massachusetts
- Mansion rentals Massachusetts
- Cottage rentals Massachusetts
- Beachfront rentals Massachusetts
- Kid-friendly rentals Massachusetts
- Bed and breakfasts Massachusetts
- Rentals with a fire pit Massachusetts
- Rentals with breakfast Massachusetts
- Private suite rentals Massachusetts
- Boutique hotel rentals Massachusetts
- Beach house rentals Massachusetts
- Guesthouse rentals Massachusetts
- Pet-friendly rentals Massachusetts
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom