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

Guest suite in Tyngsborough

4.98 out of 5 average rating, 215 reviews

Lakefront Suite Two-Room, Comfy, Tranquil

Re-opening mid April! Guests can enjoy 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, 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 too!

Jul 14 – 21

G$26,120 GYD per night
Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 346 reviews

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Feb 28 – Mar 7

G$78,446 GYD per night
Guest favorite

Guest suite in Uxbridge

5.0 out of 5 average rating, 267 reviews

Beautiful, Unique, & Cozy Cedar Flat

Come enjoy this new and beautifully designed space in historic Uxbridge, MA. Set up like a tiny house, it is the most cozy and clean place you will visit. A ship’s ladder will take you to the queen loft bed or use a new PotteryBarn sleeper sofa. The Frame TV will act as a beautiful painting if you prefer to "unplug." Climate control and a hammock chair are a perfect combo! Located on a quiet street, it is an easy 25 min. drive to Providence or Worcester, and only 50 min. to downtown Boston.

Dec 1 – 8

G$29,306 GYD per night

Popular amenities for Massachusetts vacation rentals

Massachusetts waterfront vacation rentals

Guest favorite

Guest suite in Marblehead

4.92 out of 5 average rating, 243 reviews

Ocean Park Retreat

Dec 13 – 20

G$23,937 GYD per night
Superhost

Guest suite in Charlton

4.86 out of 5 average rating, 378 reviews

Baker Pond Hideaway

May 24 – 31

G$24,834 GYD per night
Guest favorite

Loft in Rockport

5.0 out of 5 average rating, 194 reviews

Chic Downtown Loft ☆ Private Parking ☆ Ocean View

Nov 13 – 20

G$32,765 GYD per night
Guest favorite

Cottage in Plymouth

4.93 out of 5 average rating, 222 reviews

Ocean View Cottage

Dec 15 – 20

G$36,114 GYD per night
Guest favorite

Loft in Gloucester

4.9 out of 5 average rating, 167 reviews

Rocky Neck Studio/Loft, Gloucester, Mass.

Dec 14 – 21

G$25,668 GYD per night
Superhost

Home in Plymouth

4.88 out of 5 average rating, 144 reviews

OCEANFRONT Home on secluded beach.

May 22 – 29

G$89,016 GYD per night
Guest favorite

Cottage in Plymouth

4.96 out of 5 average rating, 160 reviews

Stunning ocean views, stairs down to the beach

Mar 12 – 19

G$100,211 GYD per night
Superhost

Cottage in Dennis

4.88 out of 5 average rating, 344 reviews

Waterfront Cottage on White Pond(Graham Cracker)

Apr 11 – 18

G$30,352 GYD 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

G$42,109 GYD per night
Guest favorite

Place to stay in Falmouth

4.94 out of 5 average rating, 297 reviews

Cottage facing fresh water pond

Dec 13 – 20

G$30,218 GYD 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

G$38,839 GYD per night
Guest favorite

Guest suite in Orleans

4.91 out of 5 average rating, 141 reviews

Charming Old Cape Cod

Sep 12 – 19

G$30,888 GYD per night

Massachusetts fishing vacation rentals

Guest favorite

Home in Southwick

4.99 out of 5 average rating, 177 reviews

Linny's Lakeview Cottage

Nov 19 – 26

G$29,169 GYD per night
Guest favorite

Cottage in Eastham

4.9 out of 5 average rating, 342 reviews

Barn Cottage on Minister Pond

Sep 29 – Oct 6

G$29,972 GYD per night
Guest favorite

Home in Norton

4.9 out of 5 average rating, 173 reviews

THE RED HOUSE - Entire Private Home

Jul 25 – Aug 1

G$29,093 GYD per night
Guest favorite

Apartment in Great Barrington

4.95 out of 5 average rating, 314 reviews

Private En Suite in Beautiful Victorian

Dec 11 – 18

G$23,113 GYD per night
Guest favorite

Apartment in Natick

4.98 out of 5 average rating, 330 reviews

Scandi-Modern Apartment

Sep 4 – 11

G$26,534 GYD per night
Guest favorite

Cottage in Ashfield

4.97 out of 5 average rating, 296 reviews

hope house

Feb 26 – Mar 5

G$34,828 GYD 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!

Dec 5 – 12

G$69,442 GYD per night
Guest favorite

Cottage in Sturbridge

4.93 out of 5 average rating, 121 reviews

Cozy Cottage on Cedar Lake- "Cottage Cheeze"

Apr 28 – May 5

G$53,199 GYD per night
Superhost

Home in Winchendon

4.8 out of 5 average rating, 138 reviews

Waterfront home 2 bedrooms withdeck beach and dock

Jun 20 – 27

G$31,018 GYD per night
Superhost

Cottage in Shutesbury

4.93 out of 5 average rating, 194 reviews

Lake Wyola House Shutesbury Massachusetts

Oct 15 – 22

G$35,477 GYD per night
Guest favorite

Cottage in Becket

4.95 out of 5 average rating, 122 reviews

Cozy lakeside cottage

Aug 18 – 25

G$100,980 GYD per night
Guest favorite

Cottage in Eastham

4.95 out of 5 average rating, 204 reviews

The Breeze Overlooking Minister's Pond

Apr 18 – 25

G$40,564 GYD per night

Massachusetts home rentals

Guest favorite

Home in Plymouth

4.94 out of 5 average rating, 109 reviews

Romantic Get-Away or Fun filled Family Vacation

Dec 8 – 15

G$26,712 GYD per night
Guest favorite

Home in Dalton

4.91 out of 5 average rating, 112 reviews

The Yellow House

Feb 23 – Mar 2

G$18,826 GYD per night
Guest favorite

Home in Lynn

4.91 out of 5 average rating, 225 reviews

Clean, spacious In-Law Suite -Near Everything

Nov 10 – 17

G$30,404 GYD per night
Guest favorite

Home in Ware

4.88 out of 5 average rating, 102 reviews

Little House Inn

Oct 17 – 24

G$31,667 GYD per night
Superhost

Home in Revere

4.8 out of 5 average rating, 137 reviews

Renovated Cozy City Getaway

Mar 1 – 8

G$20,716 GYD per night
Guest favorite

Home in Middleborough

4.94 out of 5 average rating, 294 reviews

Private retreat setting on 4 acres 1

Nov 12 – 19

G$21,081 GYD per night
Guest favorite

Home in Quincy

4.96 out of 5 average rating, 121 reviews

Artist's Haven (2)

Jun 8 – 15

G$24,176 GYD per night
Guest favorite

Home in Dedham

4.85 out of 5 average rating, 485 reviews

Private apartment close the city!

Apr 17 – 24

G$16,304 GYD per night
Guest favorite

Home in Feeding Hills

4.89 out of 5 average rating, 875 reviews

Farm Fresh Feeding Hills

Aug 31 – Sep 7

G$25,201 GYD per night
Guest favorite

Home in Williamsburg

4.99 out of 5 average rating, 155 reviews

Hilltown Studio

Aug 29 – Sep 5

G$25,769 GYD per night
Guest favorite

Home in Mattapoisett

4.94 out of 5 average rating, 126 reviews

*The Cozy Escape* | Historic South Coast Retreat

Dec 8 – 15

G$40,806 GYD per night
Guest favorite

Home in Billerica

4.97 out of 5 average rating, 149 reviews

Residential home ▪ Billerica ▪ quiet, clean & cozy

Jan 5 – 12

G$32,155 GYD 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