The Best Seaside Towns to Visit in Massachusetts

Massachusetts has a rich seafaring history and plenty of storied landmarks, like Brant Point Light Station
Massachusetts has a rich seafaring history and plenty of storied landmarks, like Brant Point Light Station | © Lighthouses by Allan Wood / Alamy Stock Photo
Photo of Debra Smith
12 April 2021

The coast of Massachusetts is littered with beautiful beaches for swimming and sunbathing in the summer. But many of its towns – from Martha’s Vineyard to Nantucket and Gloucester – 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 hotels to help you get planning, all bookable with Culture Trip.

Oak Bluffs, Martha's Vineyard

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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-style cottages. There are more than 300, all of which were part of the first summer religious camp in the United States.

Where to stay on Martha’s Vineyard

Harbor View Hotel

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Harbor View Hotel
Courtesy of Harbor View Hotel / Expedia.com
This historic hotel has been pleasing guests for over 130 years. Clad in classic wooden shingles, with a white wraparound veranda, the hotel’s 117 rooms command the best views on the island. Rooms and suites are beach-luxe, with private balconies, Molton Brown bath products, and Frette linens. Hop on a fat-tire bike and fill your wicker basket with goodies from the boutiques and galleries in town, or take the courtesy car, a Mercedes-Benz, for a spin around the island. Oak Bluffs is just a 15-minute drive away.
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Vineyard Square Hotel & Suites

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Vineyard Square Hotel & Suites
Courtesy of Vineyard Square Hotel and Suites / Expedia.com
Feel the sand between your toes at the nearby historic Edgartown Lighthouse, or at the beaches where Jaws was filmed. Vineyard Square makes it easy for you with beach chairs, umbrellas, and towels on loan. Enjoy first-class harbor views from the collection of rooms and suites at the hotel, and sip your morning coffee on one of the rocking chairs strategically placed on the veranda. Instead of chocolates, you’ll find local taffy at turndown.

Summercamp Hotel

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Summercamp Hotel
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Like the historic Methodist Church campground it sits next to, Summercamp is open seasonally from early spring until late fall. Its weathered cedar, five-story facade still says 1879, but inside it’s 1969, all sunshine colors and geometric shapes. Most of the 95 rooms and suites overlook Oak Bluffs Harbour, but views from multiple porches, complete with rocking chairs, are free for all guests. Tour the island, borrow a bike and explore the town of Oak Bluffs, or just watch the waves from a hanging basket chair.

Gloucester

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Gloucester is a charming coastal town on the north shore of Massachusetts, and once a major shipbuilding hub. Take a tour through the stunning seaside Hammond Castle and learn about the famous Gloucester Fisherman’s Memorial. For a beach day, head straight to Good Harbor sandy beach, surrounded by marshes and dunes. Come dinner, pop into one of the many seafood restaurants for fresh lobster caught just off the coast.

Where to stay in Gloucester

Beauport Hotel

Boutique Hotel
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Beauport Hotel
Courtesy of Beauport Hotel / Expedia.com
Colorful beach umbrellas blossom on the sandy beach in front of the Beauport Hotel. This hotel offers amenities not normally available in historic properties, like the rooftop patio with outdoor heated pool, hot tub, bar and stunning views of the harbour. Once the oldest fishing port in America, Gloucester has become one of the world’s top five whale watching destinations, according to the World Wildlife Fund. Although it’s right in the center of town, surrounded by fine restaurants, don’t miss the crab cakes at the hotel’s own dining establishment.
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Provincetown

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Provincetown, at the very end of Cape Cod, is a top tourist destination in summer. Historically, it’s the place where the Mayflower landed in 1620, bringing over pilgrims from England. 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.

Where to stay in Provincetown

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  • Crowne Pointe Historic Inn & Spa

    Spa Hotel, Hotel
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    Crowne Pointe Historic Inn & Spa
    Courtesy of Crowne Pointe Historic Inn and Spa / Expedia.com
    This lovingly restored, former sea captain’s mansion has proven itself irresistible to former visitors, including the original owner who has been spotted wafting down corridors and opening the door to the kitchen. Perhaps he’s looking for the pastries that are served at afternoon tea, or the wine and cheese for the evening get-togethers. Six historic buildings enclose the beautifully landscaped courtyard of the inn, which is set on a windswept bluff. Be blown away by the views and the amenities at this adults-only property.
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    Benchmark Inn

    Inn
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    Benchmark Inn
    Courtesy of Benchmark Inn / Expedia.com
    The Benchmark is a three-story historic home in the Gallery District, which has been carefully restored by the current owners, Dan and Daniel. Service, conducted in several languages, is outstanding, and attracts an international clientele. A delicious extended brunch continues with beverages, pastries, and fresh fruit until 11am. The seven guest rooms feature waterfall showers, original pine floors, and separate entrances. Many have private balconies with views of the Pilgrim Monument.
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    Rockport

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    Rockport is a picturesque seaport village at the tip of the Cape Ann peninsula. Take pictures of Motif #1 – a 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 1 mile (1.6km) path to reach a vista overlooking the water, where you’ll be able to see the coasts of New Hampshire and Maine.

    Where to stay in Rockport

    Rockport Inn & Suites

    Inn
    Map View
    Rockport Inn And Suites
    Courtesy of Rockport Inn and Suites / Expedia.com
    As pretty as a picture, the Rockport’s two-story townhouse suites and beachy rooms will make you want to hang around a bit longer. Visit the pool and hot-tub building where the roof resembles an overturned rowboat. After a complimentary breakfast, rent a bike or a kayak, and catch an evening bite at a local diner in the birthplace of fried clams. Bonus: pets are welcome here, too.
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    Emerson Inn

    Inn
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    Emerson Inn
    Courtesy of Emerson Inn / Expedia.com
    If you’re drawn to the ocean, the Emerson is a perfect place to be. Within walking distance of several fine beaches, it’s also close to Cathedral Rocks, a renowned spot for deep dives and huge lobsters. Above the waves, whale sightings are possible from the shore and you can visit the nearby twin lighthouses of the Cape Ann Light Station. Enjoy the best of both worlds at the inn’s heated outdoor pool, open seasonally.

    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: you 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.

    Where to stay on Natucket

    Jared Coffin House

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    Jared Coffin House
    Courtesy of Jared Coffin House / Expedia.com
    Built in 1845 by whaling ship owner Jared Coffin, this three-story, colonial-style brick mansion was the first to be built on Nantucket Island. Handy for whalers, and for you, it’s right up the street from the ferry. Enjoy breakfast on the sheltered patio, then explore the nearby Whaling Museum or charming Historic District. The pre-arrival concierge service can help you plan everything from dinner reservations to picnics.
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    The Wauwinet

    Independent Hotel
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    The Wauwinet
    Courtesy of The Wauwinet / Expedia.com
    An elegant getaway on a quieter part of the island, the Wauwinet is a Relais et Chateau inn, with impeccable service and luxurious amenities. Enjoy a glass of prosecco in the fragrant garden, stroll one of two close beaches, or take a shuttle across Nantucket Harbor to see historic downtown, the heart of the island. Watch for deer, raptors, and seals at the Coskata-Coatue Wildlife Refuge, while seeking your own refuge from the busy off-island world.

    Ashley Kane and Christina Collins contributed additional reporting to this article.

    These recommendations were updated on April 12, 2021 to keep your travel plans fresh.

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