Massachusetts vacation rentals

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Top-rated vacation rentals in Massachusetts

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Cottage in Bourne

5.0 out of 5 average rating, 143 reviews

140 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

ﺩ.ﺇ490 per night
Guest favorite

Guest suite in Tyngsborough

4.98 out of 5 average rating, 215 reviews

Lakefront 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

ﺩ.ﺇ459 per night
Superhost

Farm stay in Southbridge

4.88 out of 5 average rating, 286 reviews

Scandanavian 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

ﺩ.ﺇ458 per night

Popular amenities for Massachusetts vacation rentals

Massachusetts waterfront vacation rentals

Superhost

Guest suite in Charlton

4.86 out of 5 average rating, 378 reviews

Baker Pond Hideaway

Nov 20 – 27

ﺩ.ﺇ443 per night
Guest favorite

Guest suite in Marblehead

4.92 out of 5 average rating, 244 reviews

Ocean Park Retreat

Nov 30 – Dec 7

ﺩ.ﺇ420 per night
Guest favorite

Cottage in Plymouth

4.93 out of 5 average rating, 222 reviews

Ocean View Cottage

Nov 5 – 10

ﺩ.ﺇ634 per night
Superhost

Home in Plymouth

4.88 out of 5 average rating, 144 reviews

OCEANFRONT Home on secluded beach.

May 22 – 29

ﺩ.ﺇ1,563 per night
Guest favorite

Loft in Gloucester

4.9 out of 5 average rating, 167 reviews

Rocky Neck Studio/Loft, Gloucester, Mass.

Jan 1 – 8

ﺩ.ﺇ451 per night
Guest favorite

Cottage in Plymouth

4.96 out of 5 average rating, 160 reviews

Stunning ocean views, stairs down to the beach

Feb 23 – Mar 2

ﺩ.ﺇ1,760 per night
Guest favorite

Apartment in Salem

4.95 out of 5 average rating, 600 reviews

Historic Salem Oceanfront 2 Rm Apt

May 19 – 24

ﺩ.ﺇ740 per night
Guest favorite

Cabin in Hubbardston

4.94 out of 5 average rating, 140 reviews

Triggers Cabin

Nov 26 – Dec 3

ﺩ.ﺇ570 per night
Guest favorite

Cabin in Littleton

4.98 out of 5 average rating, 113 reviews

Private & Remote, Enjoy Outdoors, Sleep in Luxury

May 31 – Jun 7

ﺩ.ﺇ647 per night
Guest favorite

Cottage in Yarmouth

4.95 out of 5 average rating, 177 reviews

Cozy Coastal Cottage With Sprawling Sea Views

Oct 12 – 19

ﺩ.ﺇ682 per night
Guest favorite

Guest suite in Gloucester

4.98 out of 5 average rating, 374 reviews

SplashLanding Private Beach Getaway in Gloucester

Oct 1 – 8

ﺩ.ﺇ1,356 per night
Guest favorite

Cottage in Sandwich

4.95 out of 5 average rating, 155 reviews

Waterfront Lake Cottage, Private Beach, Wow View!

Jan 13 – 20

ﺩ.ﺇ1,418 per night

Massachusetts fishing vacation rentals

Guest favorite

Cottage in Eastham

4.9 out of 5 average rating, 342 reviews

Barn Cottage on Minister Pond

Sep 29 – Oct 6

ﺩ.ﺇ526 per night
Guest favorite

Home in Norton

4.9 out of 5 average rating, 173 reviews

THE RED HOUSE - Entire Private Home

May 21 – 28

ﺩ.ﺇ511 per night
Guest favorite

Apartment in Great Barrington

4.95 out of 5 average rating, 314 reviews

Private En Suite in Beautiful Victorian

Mar 18 – 25

ﺩ.ﺇ406 per night
Guest favorite

Cottage in Ashfield

4.97 out of 5 average rating, 296 reviews

hope house

Jul 26 – Aug 2

ﺩ.ﺇ612 per night
Guest favorite

Home in Southwick

4.99 out of 5 average rating, 177 reviews

Linny's Lakeview Cottage

Jul 31 – Aug 7

ﺩ.ﺇ635 per night
Guest favorite

Apartment in Natick

4.98 out of 5 average rating, 330 reviews

Scandi-Modern Apartment

Sep 5 – 12

ﺩ.ﺇ466 per night
Guest favorite

Cottage in Sturbridge

4.93 out of 5 average rating, 121 reviews

Cozy Cottage on Cedar Lake- "Cottage Cheeze"

Apr 29 – May 6

ﺩ.ﺇ934 per night
Guest favorite

Home in Sturbridge

4.94 out of 5 average rating, 207 reviews

Lake Front Home Sleeps 6-8 on a private Peninsula!

Nov 15 – 22

ﺩ.ﺇ1,561 per night
Guest favorite

Guest suite in Sharon

4.97 out of 5 average rating, 142 reviews

Cozy Lakeview Guesthouse

Mar 11 – 18

ﺩ.ﺇ642 per night
Guest favorite

Cottage in Becket

4.94 out of 5 average rating, 237 reviews

BERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.

Oct 18 – 25

ﺩ.ﺇ694 per night
Guest favorite

Apartment in Medford

4.92 out of 5 average rating, 253 reviews

Garden Apartment for Vacation & Business Travelers

Jun 4 – 11

ﺩ.ﺇ549 per night
Guest favorite

Cottage in Becket

4.95 out of 5 average rating, 122 reviews

Cozy lakeside cottage

Jul 10 – 17

ﺩ.ﺇ1,566 per night

Massachusetts home rentals

Guest favorite

Home in Dalton

4.91 out of 5 average rating, 112 reviews

The Yellow House

Feb 12 – 19

ﺩ.ﺇ331 per night
Guest favorite

Home in Plymouth

4.94 out of 5 average rating, 109 reviews

Romantic Get-Away or Fun filled Family Vacation

Feb 7 – 14

ﺩ.ﺇ469 per night
Guest favorite

Home in Ware

4.88 out of 5 average rating, 102 reviews

Little House Inn

Apr 20 – 27

ﺩ.ﺇ467 per night
Guest favorite

Home in Lynn

4.91 out of 5 average rating, 225 reviews

Clean, spacious In-Law Suite -Near Everything

Dec 30 – Jan 6

ﺩ.ﺇ534 per night
Superhost

Home in Revere

4.8 out of 5 average rating, 138 reviews

Renovated Cozy City Getaway

Feb 10 – 17

ﺩ.ﺇ364 per night
Guest favorite

Home in Middleborough

4.94 out of 5 average rating, 294 reviews

Private retreat setting on 4 acres 1

Jan 17 – 24

ﺩ.ﺇ370 per night
Guest favorite

Home in Quincy

4.96 out of 5 average rating, 121 reviews

Artist's Haven (2)

Jun 11 – 18

ﺩ.ﺇ425 per night
Guest favorite

Home in North Truro

4.98 out of 5 average rating, 261 reviews

Beautiful North Truro cottage with screen porch

Jan 15 – 22

ﺩ.ﺇ578 per night
Guest favorite

Home in Feeding Hills

4.9 out of 5 average rating, 877 reviews

Farm Fresh Feeding Hills

Sep 10 – 17

ﺩ.ﺇ442 per night
Guest favorite

Home in Williamsburg

4.99 out of 5 average rating, 155 reviews

Hilltown Studio

Feb 6 – 13

ﺩ.ﺇ453 per night
Guest favorite

Home in Billerica

4.97 out of 5 average rating, 149 reviews

Residential home ▪ Billerica ▪ quiet, clean & cozy

Feb 10 – 17

ﺩ.ﺇ565 per night
Guest favorite

Home in Truro

4.88 out of 5 average rating, 167 reviews

Cape Cod Getaway 2 Bedroom Cozy Home

Nov 12 – 19

ﺩ.ﺇ579 per night

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