Massachusetts vacation rentals
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Top-rated vacation rentals in Massachusetts
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Popular amenities for Massachusetts vacation rentals
Massachusetts waterfront vacation rentals
Cabin in Monterey
4.86 out of 5 average rating, 217 reviewsSecluded cabin with babbling brook
Camper/RV in Westhampton
4.88 out of 5 average rating, 148 reviewsAirbytheStream waterfront, private, clean and cozy
Guest suite in Marblehead
4.91 out of 5 average rating, 260 reviewsOcean Park Retreat
Cottage in Marion
4.99 out of 5 average rating, 138 reviewsLittle Boho Retreat by the Beach
Bungalow in Dartmouth
4.94 out of 5 average rating, 162 reviewsUpdated Vintage Bungalow with Incredible Views
Home in Agawam
4.97 out of 5 average rating, 145 reviewsSunrise on the Water's Edge - Riverside Bungalow
Rental unit in Arlington
4.98 out of 5 average rating, 184 reviewsLakeside apartment, patio, hot tub, outside shower
Guesthouse in Dartmouth
4.88 out of 5 average rating, 118 reviewsLovely Lakeside Cottage
Massachusetts fishing vacation rentals
Home in Yarmouth
5 out of 5 average rating, 279 reviewsgorgeous waterfront cottage w/4kayaks and 2 SUPs
Home in Wayland
4.77 out of 5 average rating, 460 reviewsTiny house experience steps from the water!
Home in Yarmouth Port, Cape Cod
4.99 out of 5 average rating, 325 reviewsFabulous Waterfront! 3bdrm/2bth Kayaks & Firepit
Cottage in Becket
4.95 out of 5 average rating, 266 reviewsBERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.
Home in Southwick
4.95 out of 5 average rating, 199 reviewsLinny's Lakeview Cottage
Home in Sturbridge
4.9 out of 5 average rating, 109 reviewsLuxury Lake Living
Rental unit in Otis
4.84 out of 5 average rating, 102 reviewsSpringtime Oasis in the Berkshires!
Guest suite in Brewster
4.96 out of 5 average rating, 361 reviewsSheep Pond Get-Away
Massachusetts home rentals
Home in Salisbury
4.87 out of 5 average rating, 187 reviewsSpacious 2 bedrooms waterfront free parking &Wi-fi
Home in Westport
4.9 out of 5 average rating, 503 reviewsMermaid Cottage
Home in Stoneham
4.94 out of 5 average rating, 173 reviewsEntire Apartment in Stoneham
Home in Feeding Hills
4.89 out of 5 average rating, 923 reviewsFarm Fresh Feeding Hills
Home in Quincy
4.96 out of 5 average rating, 141 reviewsArtist's Haven (2)
Home in Westminster
4.82 out of 5 average rating, 119 reviewsLakefront; view of ski mtn, firepit, dock, kayaks!
Home in Plymouth
4.89 out of 5 average rating, 238 reviewsOcean Side, Amazing View, close to town/beach, Spa
Home in Chester
4.96 out of 5 average rating, 335 reviewsRiverfront Getaway
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
- Boutique hotel rentals Massachusetts
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- Family travel hub Tips and inspiration
- Family budget travel Get there for less
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- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes