The Best Seaside Towns to Visit in Massachusetts

The coastal towns of Massachusetts, including Nantucket, offer relaxing beaches and historic landmarks
The coastal towns of Massachusetts, including Nantucket, offer relaxing beaches and historic landmarks | © Lighthouses by Allan Wood / Alamy Stock Photo
Photo of Ashley Kane
Freelance Writer24 August 2020

The coast of Massachusetts is littered with beautiful places for swimming and sunbathing on idyllic beaches in summer. But many of its towns are just as enjoyable in the off-season – and much less crowded. We’ve rounded up the best seaside spots in the Bay State – and thrown in some top-rated Airbnbs to help you get planning.

Oak Bluffs, Martha's Vineyard

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© Number 7 / Alamy Stock Photo
Oak Bluffs is a beautiful town on the island of Martha’s Vineyard. Board a ferry from the mainland, and enjoy a weekend exploring this summer destination. Take in the scenic views of the harbor and East Chop Light before wandering around the quaint Wesleyan Grove district, dotted with historic, ornate, gingerbread cottages. There are more than 300, all of which were part of the first summer religious camp in the United States. Today, you can rent the cottages, take walking tours or participate in spiritual services here as part of the Martha’s Vineyard Camp Meeting Association.

Cottage with views over Farm Pond

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Courtesy of Sarah / Airbnb

This private, peaceful cottage in Oak Bluffs, with panoramic views over Farm Pond and Nantucket Sound, has a simple, rustic feel with original mid-century-modern features. It’s great for families or groups wanting to get away from it all. With space for up to five guests, the cottage is part of a community with two private beaches, and there’s even a kayak here for rowing on the pond.

Furnished apartment in the heart of Gloucester

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Courtesy of James / Airbnb

This fully furnished apartment, which sleeps six, is just a five-minute walk from the beach, and handily central so you can easily visit the handful of museums, shops and restaurants here. The train station, boat shuttle and Man at the Wheel statue are all close, too. The apartment comes with a large kitchen, breakfast bar and dining table, and a living room with Netflix-ready TV for cosy nights in.

Provincetown

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© Susan E. Degginger / Alamy Stock Photo
Provincetown, at the very end of Cape Cod, is a top tourist destination in summer. Enjoy the downtown shops, spend the day at Race Point beach and chow down on fresh seafood at one of the many restaurants in town. Stop by the Lobster Pot for a delicious lobster roll, and Provincetown Portuguese Bakery for excellent breakfasts and desserts.

Float Inn at Provincetown Harbor

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Courtesy of Lory / Airbnb

A stay in Provincetown is likely to be even more memorable when your accommodation is a houseboat. Docked at Flyer’s Boatyard in Provincetown Harbor, Float Inn, which sleeps four, offers amazing views from two ground-level outdoor decks and another deck up top. You can cook burgers to your heart’s content on the grill on the back deck, and relax as the boat rocks you to sleep.

Rockport

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© Nancy Kennedy / Alamy Stock Photo
Rockport is a picturesque seaport village at the tip of the Cape Ann peninsula. Take pictures of Motif #1 the red fishing shack – so named in 1945 because it was always featuring in paintings of the town – before wandering around the art galleries and shops. Halibut Point State Park is nearby if you’d like to get closer to the ocean. Walk down the 1mi (1.6km) path to reach a vista overlooking the water, where you’ll be able to see the coasts of New Hampshire and Maine.

Ocean-view loft apartment on Bearskin Neck

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Courtesy of Audra / Airbnb

Perfect for couples and solo travelers, this gorgeous loft apartment on Rockport’s Bearskin Neck overlooks a small private beach. The balcony is the perfect spot to enjoy the sunset and a glass of wine, while its close proximity to shops, restaurants and Front Beach make it a convenient location for local exploration.

Nantucket

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© Susan Pease / Alamy Stock Photo
Like Martha’s Vineyard, Nantucket is only a ferry ride from the mainland. The island was a 19th-century whaling hub, and visitors can stop by the Nantucket Whaling Museum to learn more about this historic town. Though smaller than Martha’s Vineyard, there is still plenty for visitors to do here: explore boutiques downtown, relax on sandy, dune-backed beaches and stroll through cobblestone streets past historic steepled churches.

Quirky and charming Hydrangea Cottage

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Courtesy of Diana / Airbnb

If you’re looking for some Old Nantucket charm with a touch of quirkiness, this beach house, sleeping six, won’t disappoint. It was built in the early 1970s by artists and still has an artsy feel, with lots of paintings on the walls, trees in the garden, and a hammock in the backyard from where you can enjoy the sunset. Only 3mi (4.8km) from Nantucket town, this is the perfect vacation spot for families.

Wellfleet

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© Wayne Bruzek / Alamy Stock Photo
Halfway between the tip and the elbow of Cape Cod, Wellfleet is a great spot to come for whale-watching tours or a round of golf; it’s also home to one of the few drive-in movie theaters left in the state. But the top draw here is Marconi beach, which got its name after the Italian inventor sent the first transatlantic wireless communication from here. Note that there are beach fees in summer. Don’t miss the Beachcomber for fresh seafood, drinks and live music. Wellfleet also has lots of bike paths, so it’s safe and easy to get around.

Hillside cottage with private deck

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Courtesy of Jeff / Airbnb

This one-bed cottage, which sleeps four, sits at the top of a wetland area in elegantly landscaped surroundings within walking distance of Lecount Hollow beach. It comprises a living room, kitchen, bathroom and private deck, and is a great spot for birdwatchers and nature lovers in general.

Christina Collins contributed additional reporting to this article

These recommendations were updated on August 24, 2020 to keep your travel plans fresh.