Massachusetts vacation rentals
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Top-rated vacation rentals in Massachusetts
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Vacation rentals for every style
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Popular amenities for Massachusetts vacation rentals
Massachusetts waterfront vacation rentals
Cottage in Plymouth
4.93 out of 5 average rating, 222 reviewsOcean View Cottage
Dec 16 – 21
Guest suite in Marblehead
4.92 out of 5 average rating, 244 reviewsOcean Park Retreat
Mar 13 – 20
Home in Plymouth
4.88 out of 5 average rating, 144 reviewsOCEANFRONT Home on secluded beach.
May 22 – 29
Cottage in Plymouth
4.96 out of 5 average rating, 160 reviewsStunning ocean views, stairs down to the beach
Feb 13 – 20
Loft in Gloucester
4.9 out of 5 average rating, 167 reviewsRocky Neck Studio/Loft, Gloucester, Mass.
Oct 13 – 20
Apartment in Salem
4.95 out of 5 average rating, 600 reviewsHistoric Salem Oceanfront 2 Rm Apt
May 19 – 24
Place to stay in Falmouth
4.94 out of 5 average rating, 297 reviewsCottage facing fresh water pond
Dec 15 – 22
Cottage in Yarmouth
4.95 out of 5 average rating, 177 reviewsCozy Coastal Cottage With Sprawling Sea Views
Oct 12 – 19
Massachusetts fishing vacation rentals
Home in Southwick
4.99 out of 5 average rating, 177 reviewsLinny's Lakeview Cottage
Nov 19 – 26
Cottage in Eastham
4.9 out of 5 average rating, 342 reviewsBarn Cottage on Minister Pond
Sep 29 – Oct 6
Home in Norton
4.9 out of 5 average rating, 173 reviewsTHE RED HOUSE - Entire Private Home
Apr 5 – 12
Apartment in Great Barrington
4.95 out of 5 average rating, 314 reviewsPrivate En Suite in Beautiful Victorian
Apr 30 – May 7
Cottage in Ashfield
4.97 out of 5 average rating, 296 reviewshope house
Jan 14 – 21
Apartment in Natick
4.98 out of 5 average rating, 330 reviewsScandi-Modern Apartment
Sep 8 – 15
Home in Sturbridge
4.94 out of 5 average rating, 207 reviewsLake Front Home Sleeps 6-8 on a private Peninsula!
Nov 15 – 22
Cottage in Shutesbury
4.93 out of 5 average rating, 194 reviewsLake Wyola House Shutesbury Massachusetts
Oct 15 – 22
Massachusetts home rentals
Home in Plymouth
4.94 out of 5 average rating, 109 reviewsRomantic Get-Away or Fun filled Family Vacation
Jan 18 – 25
Home in Dalton
4.91 out of 5 average rating, 112 reviewsThe Yellow House
Nov 30 – Dec 7
Home in Lynn
4.91 out of 5 average rating, 225 reviewsClean, spacious In-Law Suite -Near Everything
Feb 25 – Mar 4
Home in Ware
4.88 out of 5 average rating, 102 reviewsLittle House Inn
Oct 18 – 25
Home in Revere
4.8 out of 5 average rating, 138 reviewsRenovated Cozy City Getaway
Nov 13 – 20
Home in Middleborough
4.94 out of 5 average rating, 294 reviewsPrivate retreat setting on 4 acres 1
Mar 23 – 30
Home in Quincy
4.96 out of 5 average rating, 121 reviewsArtist's Haven (2)
Jun 5 – 12
Home in North Truro
4.98 out of 5 average rating, 261 reviewsBeautiful North Truro cottage with screen porch
Feb 11 – 18
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
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