Massachusetts vacation rentals
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Top-rated vacation rentals in Massachusetts
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Popular amenities for Massachusetts vacation rentals
Massachusetts home rentals
Home in Westport
4.9 out of 5 average rating, 499 reviewsMermaid Cottage
Home in Feeding Hills
4.89 out of 5 average rating, 919 reviewsFarm Fresh Feeding Hills
Home in Quincy
4.96 out of 5 average rating, 140 reviewsArtist's Haven (2)
Home in Southwick
4.95 out of 5 average rating, 198 reviewsLinny's Lakeview Cottage
Home in Westminster
4.83 out of 5 average rating, 114 reviewsLakefront; view of ski mtn, firepit, dock, kayaks!
Home in Becket
4.87 out of 5 average rating, 320 reviewsReal Estate:Therapy - Lake, Laundry, Love it
Home in Chester
4.96 out of 5 average rating, 333 reviewsRiverfront Getaway
Home in Great Barrington
4.97 out of 5 average rating, 235 reviewsJaw dropping mountain & lake views
Other great vacation rentals in Massachusetts
Cottage in Fairhaven
4.94 out of 5 average rating, 113 reviewsSeaside cottage
Guest suite in Ashburnham
4.98 out of 5 average rating, 428 reviewsThe Ginger Bed King Suite
Camper/RV in Westhampton
4.88 out of 5 average rating, 145 reviewsAirbytheStream waterfront, private, clean and cozy
Cottage in Sandwich
4.95 out of 5 average rating, 198 reviewsLakefront cottage, private Beachfront, Wow View!
Guest suite in Littleton
4.91 out of 5 average rating, 360 reviewsHistoric Loft with bathroom & kitchenette
Guest suite in Winchester
5 out of 5 average rating, 156 reviewsWarm and cozy 1st flr sweet guest suite w parking
Guest suite in Uxbridge
4.99 out of 5 average rating, 162 reviewsThe 1780 Suite
Guest suite in Blackstone
4.92 out of 5 average rating, 236 reviewsPrivate access in-law apartment, perfect for two
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
- Rentals with a home theater Massachusetts
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- Things to do Massachusetts
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