Massachusetts vacation rentals
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Top-rated vacation rentals in Massachusetts
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Cottage in Bourne
5.0 out of 5 average rating, 143 reviews140 Steps to Beach with Water Views
This small rustic unique cottage is ready for you to enjoy on Buttermilk Bay. It is located within a cape style cottage community that offers a private association beach. There are water views from both the living room and deck. Grab the provided beach chairs, water tubes, cooler and walk a 140 steps from the deck to the beach. You can also walk, bike, or fish on cape cod canal nearby. Close to restaurants, hiking trails and Golf Courses. Cape Cod Bridge 2 min away. Early Bird deals in May/Sept.
Aug 24 – 31
Guest suite in Tyngsborough
4.98 out of 5 average rating, 215 reviewsLakefront Suite Two-Room, Comfy, Tranquil
Guests can enjoy entire private suite on a lovely small lake with a panoramic view, a spa-like bathroom, cotton linens, and a comfy bed. A/C and a fireplaced living room. Quietly watch lake nature or boats going by, or venture out to swim, kayak, or fish. Enjoy Lowell's mill history and it's national park, take a forest walk nearby, or drive 10 min. to Nashua, NH for its many restaurants and tax-free shopping. One hour from Boston and central to New England highlights. Low cleaning fees!
Jul 10 – 17
Farm stay in Southbridge
4.88 out of 5 average rating, 286 reviewsScandanavian Wigwam with Sauna and Forest Baths
Deep sleeps await in our off grid forest Wigam. With everything you need, and nothing you do not, this exceptional retreat boasts a Danish Morso wood stove, fire pit, private forest baths, Finnish sauna, HUGE windows overlooking a wildlife trail and Peepers Owls and Coyote song. From photo shoots to wedding proposals - this is a special place to care for yourself and your family. We are on farm - but out of sight. Bring your kids, dogs, friends, guitar, or just a good book and settle in!
Jun 15 – 20
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Massachusetts vacation rentals
Massachusetts waterfront vacation rentals
Guest suite in Charlton
4.86 out of 5 average rating, 378 reviewsBaker Pond Hideaway
Nov 20 – 27
Guest suite in Marblehead
4.92 out of 5 average rating, 244 reviewsOcean Park Retreat
Nov 30 – Dec 7
Cottage in Plymouth
4.93 out of 5 average rating, 222 reviewsOcean View Cottage
Nov 5 – 10
Home in Plymouth
4.88 out of 5 average rating, 144 reviewsOCEANFRONT Home on secluded beach.
May 22 – 29
Loft in Gloucester
4.9 out of 5 average rating, 167 reviewsRocky Neck Studio/Loft, Gloucester, Mass.
Jan 1 – 8
Cottage in Plymouth
4.96 out of 5 average rating, 160 reviewsStunning ocean views, stairs down to the beach
Feb 23 – Mar 2
Apartment in Salem
4.95 out of 5 average rating, 600 reviewsHistoric Salem Oceanfront 2 Rm Apt
May 19 – 24
Cabin in Hubbardston
4.94 out of 5 average rating, 140 reviewsTriggers Cabin
Nov 26 – Dec 3
Cabin in Littleton
4.98 out of 5 average rating, 113 reviewsPrivate & Remote, Enjoy Outdoors, Sleep in Luxury
May 31 – Jun 7
Cottage in Yarmouth
4.95 out of 5 average rating, 177 reviewsCozy Coastal Cottage With Sprawling Sea Views
Oct 12 – 19
Guest suite in Gloucester
4.98 out of 5 average rating, 374 reviewsSplashLanding Private Beach Getaway in Gloucester
Oct 1 – 8
Cottage in Sandwich
4.95 out of 5 average rating, 155 reviewsWaterfront Lake Cottage, Private Beach, Wow View!
Jan 13 – 20
Massachusetts fishing vacation rentals
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
May 21 – 28
Apartment in Great Barrington
4.95 out of 5 average rating, 314 reviewsPrivate En Suite in Beautiful Victorian
Mar 18 – 25
Cottage in Ashfield
4.97 out of 5 average rating, 296 reviewshope house
Jul 26 – Aug 2
Home in Southwick
4.99 out of 5 average rating, 177 reviewsLinny's Lakeview Cottage
Jul 31 – Aug 7
Apartment in Natick
4.98 out of 5 average rating, 330 reviewsScandi-Modern Apartment
Sep 5 – 12
Cottage in Sturbridge
4.93 out of 5 average rating, 121 reviewsCozy Cottage on Cedar Lake- "Cottage Cheeze"
Apr 29 – May 6
Home in Sturbridge
4.94 out of 5 average rating, 207 reviewsLake Front Home Sleeps 6-8 on a private Peninsula!
Nov 15 – 22
Guest suite in Sharon
4.97 out of 5 average rating, 142 reviewsCozy Lakeview Guesthouse
Mar 11 – 18
Cottage in Becket
4.94 out of 5 average rating, 237 reviewsBERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.
Oct 18 – 25
Apartment in Medford
4.92 out of 5 average rating, 253 reviewsGarden Apartment for Vacation & Business Travelers
Jun 4 – 11
Cottage in Becket
4.95 out of 5 average rating, 122 reviewsCozy lakeside cottage
Jul 10 – 17
Massachusetts home rentals
Home in Dalton
4.91 out of 5 average rating, 112 reviewsThe Yellow House
Feb 12 – 19
Home in Plymouth
4.94 out of 5 average rating, 109 reviewsRomantic Get-Away or Fun filled Family Vacation
Feb 7 – 14
Home in Ware
4.88 out of 5 average rating, 102 reviewsLittle House Inn
Apr 20 – 27
Home in Lynn
4.91 out of 5 average rating, 225 reviewsClean, spacious In-Law Suite -Near Everything
Dec 30 – Jan 6
Home in Revere
4.8 out of 5 average rating, 138 reviewsRenovated Cozy City Getaway
Feb 10 – 17
Home in Middleborough
4.94 out of 5 average rating, 294 reviewsPrivate retreat setting on 4 acres 1
Jan 17 – 24
Home in Quincy
4.96 out of 5 average rating, 121 reviewsArtist's Haven (2)
Jun 11 – 18
Home in North Truro
4.98 out of 5 average rating, 261 reviewsBeautiful North Truro cottage with screen porch
Jan 15 – 22
Home in Feeding Hills
4.9 out of 5 average rating, 877 reviewsFarm Fresh Feeding Hills
Sep 10 – 17
Home in Williamsburg
4.99 out of 5 average rating, 155 reviewsHilltown Studio
Feb 6 – 13
Home in Billerica
4.97 out of 5 average rating, 149 reviewsResidential home ▪ Billerica ▪ quiet, clean & cozy
Feb 10 – 17
Home in Truro
4.88 out of 5 average rating, 167 reviewsCape Cod Getaway 2 Bedroom Cozy Home
Nov 12 – 19
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
- Beachfront rentals Massachusetts
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