Celebrate Thanksgiving in New England, which is the birthplace of this beloved holiday. Massachusetts is pne of the 13 original colonies, and chock-full of historic landmarks, picturesque attractions, and noteworthy regional dishes like the Boston cream pie and New England clam chowder. Vacation rentals in Massachusetts are varied and plentiful, so consider one these nine charming areas as your home away from home this Thanksgiving.

1. Boston

Source: Pixabay/tpsdave

On Thanksgiving Day, plan a grand meal at the Boston Harbor Hotel, Seaport Hotel, or a local neighborhood restaurant on Beacon Hill, such as 75 Liberty Wharf. Burn off those calories with a walk along the Boston Freedom Trail, where you can follow historical markers that tell the story of the American Revolution and beyond as you pass museums, churches, meeting houses, burial grounds, parks, and a ship. Start your holiday shopping on Black Friday at Faneuil Hall Marketplace, one of the most beloved post-Thanksgiving events in Boston. Shop for unusual gifts with a Boston flavor while watching street performers. Refresh yourself at one of the historic taverns in the Marketplace, then sample some authentic New England clam chowder across the street at North 26.

Find vacation rentals near Boston

2. Plymouth

Mayflower II in the harbor
Source: Flickr/Robert Linsdell

Enjoy a wonderful sit-down Thanksgiving meal at the Plimoth Plantation in this coastal town south of Boston. Visit the Plantation’s museum, the Wampanoag Homesite, the English Village, and the Crafts Center. Spend some time on the Mayflower II, a full-scale replica of the original 1620 Mayflower, anchored in the Pilgrim Memorial State Park alongside Plymouth Rock. Plymouth pays homage to its history with a fabulous festival the weekend before Thanksgiving; arrive early to enjoy concerts, floats, marching bands, and drum and bugle corps.

Find vacation rentals near Plymouth

3. Stockbridge

Source: Pixabay/StockSnap

Stockbridge, with its magical New England setting, is immortalized in a famous Norman Rockwell painting that depicts the village garbed in festive lights and holiday decorations. The Norman Rockwell Museum gives you a great look at American culture and history during Rockwell’s lifetime. Visit his studio on the museum grounds, then grab a bite at the on-site cafe. Start some early holiday shopping at Williams & Sons Country Store for a whimsical trip down memory lane. Amusing and witty signs greet you throughout the store as you shop for candles, simple toys, marbles, honey sticks, and penny candy.

Find vacation rentals near Stockbridge

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

4. Rockport

Source: Pixabay/pictureday

Partake in a delicious Thanksgiving meal at the Emerson Inn, snuggled in this quaint seacoast village on Cape Ann. Choose from cider-brined turkey, juicy roasted tenderloin, or buttercrumb-topped haddock, then go for a stroll on the windswept beach or stop by one of the local artist studios to purchase an authentic landscape piece. Black Friday and Small Business Saturday in downtown Rockport are relaxing alternatives to crowded malls, so check out Christmas in the Cove for handmade gifts and baked goods. Check the schedule at the Shalin Liu Performance Center to see what performances will be on stage while you’re there.

Find vacation rentals near Rockport

5. Hancock

Berkshire Shaker Village
Source: Flickr/Jim Lukach

Outdoor enthusiasts love to spend Thanksgiving skiing and boarding at the Jiminy Peak Ski Resort in the Berkshires near Hancock. You can enjoy day or lighted night skiing on 167 acres with nine lifts and 45 runs that range from beginner to advanced. If you prefer to stay in town, spend Thanksgiving weekend at the Hancock Shaker Village, then mingle with the animals in the historic Round Stone Barn. Meander along the Farm and Forest Trail on foot or snowshoes, then visit the 19th century Brick Dwelling to learn about the Shakers’ lifestyle and view crafts and artifacts associated with their times. Spend Black Friday shopping at the Shaker Mercantile to find one-of-a-kind handmade goods, including many local artisan creations. Warm up at the Seeds Market Cafe with warm spiced local cider and autumn treats.

Find vacation rentals near Hancock

6. Worcester

Source: Pixabay/Efraimstochter

Worcester is a vibrant city in the heart of New England. Get a head start on your holiday shopping at the Holiday Festival of Crafts, Worcester’s answer to Black Friday’s big-box madness. Shop for unusual handmade gifts from over 60 fine craft artists who bring high-caliber talent to this European-style marketplace. Make a trip to the family-friendly EcoTarium to enjoy unusual interactive exhibits, such as “From Tooth to Tush,” which takes you on a digestive journey through a dinosaur’s body. The planetarium show explores the amazing pterosaurs, whose 40-foot wingspans matched that of a modern jet plane.

Find vacation rentals near Worcester

7. New Bedford

Source: Pixabay/Free-Photos

Plan on a Thanksgiving feast at Dillon’s, the Cobblestone, or Just Another Phoenix; then, take a walk around the New Bedford Whaling National Historic Park. View original equipment and artifacts from the whaling industry, including an original whaleboat, scrimshaw, and coachwhipping. Learn about the highly valued whales and their contributions to life in early New England. Get a good night’s sleep before heading out for holiday shopping at the Dartmouth Mall or the family-owned Bedford Merchant, a classic gift shop.

Find vacation rentals near New Bedford

8. Salem

Ropes Mansion
Source: Flickr/massmatt

Famous for its 17th century witch trials, Salem played a key role in Puritan American history. Become familiar with Witch City on a guided walking tour chronicling the history of Salem, with stops at the Seven Gables House, the Burial Point, the Salem Witch Trials Memorial, and the Witch House. The Peabody Essex Museum houses art and artifacts from around the world, including a restored Qing-era Chinese house. Visit Nathaniel Hawthorne’s birthplace at Canobie Lake. Take in the views from Pickering Wharf while having lunch by the sea at Finz or Vic’s Boathouse.

Find vacation rentals near Salem

9. Cape Cod

leaves and lighthouse
Source: Flickr/Massachusetts Office of Travel & Tourism

Find time for the annual Lobster Pot Christmas Tree Lighting in Provincetown the night before Thanksgiving. More than 100 lobster pots are stacked two stories high and festooned with ribbons, garlands, and thousands of festive lights. Whip up an appetite for a Thanksgiving feast on the 3.1-mile Turkey Trot run along Chatham’s scenic byways. Spend Thanksgiving Day on a leisurely, three-hour cruise down the Cape Cod Canal in climate-controlled cars while you enjoy the scenery and a fabulous five-course meal. Shop until you drop on Black Friday weekend at the Cape Cod Mall, the Mashpee Commons, or independent shops. Stop by the Chatham Candy Manor for some seaside-inspired chocolate sailboats or shells, creamy fudge, or nutty pecan turtles.

Find vacation rentals near Cape Cod

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