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Massachusetts vacation rentals
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Top-rated vacation rentals in Massachusetts
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Massachusetts home rentals
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Home in Southwick
4.95 out of 5 average rating, 196 reviewsLinny's Lakeview Cottage
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Home in Quincy
4.96 out of 5 average rating, 131 reviewsArtist's Haven (2)
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Home in Great Barrington
4.96 out of 5 average rating, 223 reviewsJaw dropping mountain & lake views
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Home in Winchendon
4.82 out of 5 average rating, 168 reviewsWaterfront home 2 bedrooms withdeck beach and dock
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Home in Middleborough
4.94 out of 5 average rating, 301 reviewsPrivate retreat setting on 4 acres 1
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Home in Agawam
4.98 out of 5 average rating, 110 reviewsSunrise on the Water's Edge - Riverside Bungalow
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Home in Chatham
4.83 out of 5 average rating, 144 reviewsDelightful Chatham Cottage, Cheerful and Clean
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Home in New Bedford
4.99 out of 5 average rating, 194 reviewsHistoric Cobblestone Carriage House near Downtown
Other great vacation rentals in Massachusetts
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Cottage in Gloucester
4.96 out of 5 average rating, 110 reviewsSunny & private cottage in Lanesville Village
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Guesthouse in Barnstable
5 out of 5 average rating, 117 reviewsModern Fireplaced Carriage House with Beach Permit
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Guest suite in Rockport
4.99 out of 5 average rating, 631 reviewsHalibut Point State Park. Nature Lovers Retreat
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Guesthouse in Framingham
4.98 out of 5 average rating, 225 reviewsPrivate guest house on beautiful country road
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Camper/RV in Wilbraham
4.96 out of 5 average rating, 200 reviewsThe Waddle on Inn
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Guesthouse in Falmouth
4.9 out of 5 average rating, 243 reviewsWooded studio apartment in Woods Hole village
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Place to stay in Falmouth
4.95 out of 5 average rating, 300 reviewsCottage facing fresh water pond
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Rental unit in Fairhaven
4.97 out of 5 average rating, 220 reviewsHistoric Fairhaven Village Garden-Level Suite
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
- Barn rentals Massachusetts
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