Massachusetts is a wonderful place to celebrate winter holidays, with old-fashioned Christmas celebrations spread across the state. Whichever city or town you visit in this historic state, you can find welcoming Massachusetts vacation rentals that range from spacious urban condos to cozy houses in the suburbs. Look forward to local Christmas parades, pageants and ballets, tours of holiday decorations, and plenty of shopping. Take a look at the seven Massachusetts towns that celebrate Christmas best.

1. Somerville

If you’re having a Boston-based Christmas, look for a vacation rental in Somerville to put yourself near the Illumination Trolley Tour. Many residents in Somerville go all out decorating for the holidays, and this tour takes you to the very best of them each year. Enjoy complimentary hot chocolate and cookies on the trolley, and encourage your kids to participate in the crafts to make it an evening to remember. If you want to burn off the cookie calories, bring your bikes on vacation, deck them out with lights, and take part in the Illumination Bike Tour.

Find vacation rentals near Somerville

2. Sturbridge

About 10 miles east of Springfield is the village of Sturbridge, where the local living history museum brings Christmas traditions alive every year. Take the kids to enjoy bunch with Santa, and enjoy beautiful concerts of Victorian Christmas carols. Roast some chestnuts over an open fire, decorate your own gingerbread house, or jingle all the way as you take an actual sleigh ride. Old Sturbridge Village also features holiday magic shows that delight the young and old.

Find vacation rentals near Sturbridge

Find the perfect Massachusetts vacation rental on is the world's #1 vacation rental search engine with over 10 million properties!

3. Marblehead

North of Boston, Marblehead gets the holiday season started early with its famous Christmas Walk at the beginning of December. Stroll through the town to enjoy holiday goodies and activities at local businesses (as well as plenty of sales to get your shopping started), and marvel at the ingenuity shown at the gingerbread festival. The town lights its Christmas tree during the festivities, and Santa Claus and Mrs. Santa make a grand arrival by boat in the harbor. Look for live entertainment at stages all over town, as well as kid-friendly activities, and don’t miss the artisan craft festivals, where you can find truly unique presents to slip under the tree.

Find vacation rentals near Marblehead

4. Stockbridge

If you’re looking for a Norman Rockwell Christmas, then Stockbridge is the place you want to be. This town inspired Rockwell’s famous painting “Stockbridge Main Street at Christmas,” and the whole town recreates the image live every year, complete with vintage cars lining the streets. Take holiday tours to view homes specially decorated for the season, or attend a local Christmas concert. The festivities also include a visit with Santa, Christmas caroling, horse-drawn carriage rides through the streets, and special Christmas foods that you can sample downtown or take back to enjoy with your family at your cozy vacation rental.

Find vacation rentals near Stockbridge

5. Rockport

Christmas goes nautical in Lockport, where Santa sails into town on a lobster boat on Christmas morning. Book a vacation rental in the heart of downtown to be in the middle of the action, which includes community carol singalongs, candy-making demonstrations, and strolling musicians wandering through town. The yearly Christmas stroll lets you visit welcoming stores to get gift ideas while featuring holiday fairs, and the Christmas pageant, which has been happening every year for more than 70 years, recreates the Nativity story by torchlight.

Find vacation rentals near Rockport

6. Boston

Boston festoons itself with light during the holiday season. Check out the light show at Faneuil Hall, stroll under the sparkling trellis at Christopher Columbus Waterfront Park, or show up at Boston Common for the official lighting of the city’s Christmas tree. Kids have a wonderful time at Symphony Hall enjoying the traditional Holiday Pops Christmas Party concerts, or pick up tickets to enjoy a performance of “The Nutcracker” at the Boston Opera House. Christmas shopping clicks into high gear at the SoWa Holiday Market as well as at the holiday fairs at Harvard Square, where you can find incredible artworks from local artisans. Experience the spiritual side of the holiday with the Candlelight Carol services at Copley Square’s Trinity Church, or enjoy the lighter side of the season by lining the streets for (or participating in) the Santa Speedo Run, a charity run with all participants wearing only Speedo swimsuits and Santa Claus hats.


Find vacation rentals near Boston

7. Newburyport

Unpack your suitcase in a vacation rental in the quaint town of Newburyport to enjoy a fun, old-fashioned holiday. Line the streets with the locals for the Santa Parade, with Santa arriving on a U.S. Coast Guard cutter, and head to the town square for the tree lighting. Newburyport takes holiday shopping to new levels with their Invitation Nights – which, paradoxically, don’t require an invitation. Wander through downtown or the Tannery Marketplace to get your shopping done with great discounts and treats handed out at almost every store. Don’t miss the punch at Partridge in a Bear Tree, then head back to your vacation rental to get all those packages wrapped.

Find vacation rentals near Newburyport

Ready to go? Check out these amazing Massachusetts vacation rentals on