Massachusetts offers many exciting cities and small towns ideal for a memorable weekend getaway. Tour the House of the Seven Gables in Salem; enjoy pastries in Boston’s North End; or hike Mount Greylock near Pittsfield. From the coastal town of Rockport to the mountain villages in the Berkshires, there is something for everyone in this quaint New England state. Book a stay at a Massachusetts vacation rental today. Take a look at some of the best weekend getaway spots in Massachusetts.

1. Boston

Boston

Boston is a bustling, compact city that has plenty of sites and activities within walking distance. Start the morning with breakfast at Trident Booksellers and Cafe before spending the day walking the Freedom Trail, linking 16 different sites from the American Revolution. Kids love going on a Duck Tour, which winds through the city before splashing down into the Charles River for a trip along the shore. In the evening, head over to the North End for dinner at La Famiglia Giorgio’s, followed by a cannoli from Mike’s Pastry.

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2. Salem

Salem

The historic city of Salem is known for its witch trials, but offers much more to see and do. Learn more about its maritime and literary history with a tour of the House of the Seven Gables and the surrounding gardens. In the afternoon, grab lunch from Flying Saucer Pizza Company or Milk and Honey before heading to Derby Wharf for a picnic along the water. For nighttime fun, take a ghost tour with Black Cat Tours and see a different side of the city.

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3. Plymouth

Plymouth
Source: Wikimedia Commons/Upstateherd

History buffs love vacationing in Plymouth, home to Plymouth Rock. Stop by to see the famous rock in Pilgrim Memorial State Park, then enjoy the scenery among the trees and along the harbor. Kids and adults alike have fun seeing the colonial era come alive at Plimouth Plantation, which recreates a village from 1627. The town’s location on the water is perfect for whale watching, so be sure to include a cruise to Stellwagen Banks. If you are hungry, try local seafood from Wood’s Seafood, East Bay Grill, or Lobster Hut.

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4. Rockport

Rockport
Source: Wikimedia Commons/Adavyd

The charming town of Rockport is small enough that vacation rentals are within walking distance of the major sites. This quintessential New England maritime town is packed with shopping, dining, and art. The colorful buildings of Bearskin Neck offer unique shops, such as Lula’s Pantry and The Pewter Shop. Fill up your bag with penny candy from The Bearskin Neck Country Store or taste delicious fudge at The Fudgery. The entire family can get out onto the water with a kayak rental from North Shore Kayak. For dinner, head to Roy Moore’s Fish Shack for classic seafood favorites with a stunning view of the ocean.

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5. Provincetown

Provincetown

Provincetown offers a great blend of activity and relaxation. Spend time near the water by swimming at Herring Cove, biking the dunes at Cape Cod National Seashore Park, or lounging in the sand at Race Point Beach. Most of the town’s shopping and dining is centered along Commercial Street. Stroll down this thoroughfare to check out Room 68 for home decor or The Shell Shop for fun souvenirs. Grab a bite to eat at Bubala’s by the Bay, Provincetown Portuguese Bakery, or Canteen.

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6. Northampton

Northampton
Source: Flickr/6SN7

Northampton is an eclectic city in the heart of beautiful Pioneer Valley. There are plenty of vacation rentals that give you easy access to Main Street for its diverse collection of shops, food, and entertainment. Start with coffee and pastries from Rao’s Coffee & Cafe, then take a peek at Thorne’s Marketplace, an indoor center of local shops, such as Booklink Booksellers and The Blue Marble. Kids and adults alike love visiting the Very Hungry Caterpillar at the Eric Carle Museum. For dinner, choose from diverse offerings, including Lhasa Cafe, Northampton Brewery, and Ibiza Tapas.

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7. Pittsfield

Pittsfield
Source: Flickr/Massachusetts Office of Travel & Tourism

For a weekend in the Berkshires, a visit to the town of Pittsfield is an excellent choice. This town is close to Mount Greylock, where you can hike to the summit for a spectacular view of the valleys below. Back in town, stop by The Marketplace Cafe for tasty sandwiches or Baba Louie’s for hearty pizza. Take in the art of Lichtenstein Center for the Arts or create your own art at Beads, Bisque and Beyond. In the evening, both the Barrington Stage Company and The Colonial Theatre offer a great selection of performances suitable for the whole family.

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8. Nantucket

Nantucket

Sometimes you want vacation destinations that are more about relaxing, and Nantucket is the perfect answer. This historic island is a quick ferry ride from the mainland and offers historic sites, waterfront dining, and peaceful beaches for napping. In town, check out the Nantucket Whaling Museum to hear about its whaling past, or visit Nantucket Lightship Basket Museum to learn about the island’s folk art. If you prefer, spend your entire weekend at the beach. The calm water of Children’s Beach is perfect for families with little ones, while Cisco Beach is better for older teens and adults. At night, enjoy a quiet meal at The Proprietors Bar & Table.

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