7 Coolest Massachusetts Towns For A Summer Vacation In 2025

With the summer season right around the corner, there isn’t much of a better state to vacation in than Massachusetts. Sandy beaches, sandcastle contests, whale watching, and theater festivals make the state’s small towns come to life in the summer months. Local inns in each town will make your vacation feel even more special. Many are historic, adding to the cultural experience. If you are still figuring out your summer plans, these seven cool towns promise a fun and memorable getaway.

Nantucket

Nantucket delivers the quintessential summer getaway that many travelers envision when they think of a small New England coastal town. Visitors can escape the summer heat at one of Nantucket’s many beaches, which are some of the most pristine in the state. Jetties Beach is a great spot for the entire family, with wide and flat shores, gentle waves, and lifeguards during the high season. Jetties Beach also holds some of the town’s key annual festivals, such as the summer Sandcastle and Sculpture Contest! During this event, residents and visitors from around the region get together to build sand castles and compete for one of the coveted ribbons.

Those in need of a new swimsuit or summer beach outfit can browse one of Nantucket’s charming boutiques, such as The Skinny Dip, located on Old South Wharf. After a day of sun and sandcastles, visitors can unwind for the night at the Brass Lantern Inn, an elegant bed and breakfast that is set in a historic home from the mid-19th century.

Gloucester

Just a 45-minute drive from Boston, Gloucester is the perfect vacation destination for Bostonians looking to avoid a lengthy drive. Visitors can kick off their trip by booking a whale watching tour with a local agency like 7 Seas Whale Watch, which gives visitors the possibility to spot humpback whales, finback whales, minke whales, and pilot whales, among many other kinds of marine life. Gloucester’s art community is also quite lively and active, which visitors can experience at The Cultural Center at Rocky Neck. The center, housed in a Carpenter Gothic building from 1877, features two floors of rotating exhibits. The Harborview Inn is a wonderful place to spend the night, located near beaches, museums, shops, and restaurants, and offering a complimentary continental breakfast each morning.

Lenox

Filled with museums and historic landmarks, travelers can explore some of the region’s most fascinating cultural attractions in Lenox. The Mount: Edith Wharton's Home is a great starting point, constructed by Edith Wharton in 1902 and featuring a historic house museum, grounds, and gardens to explore. From June 19th until Labor Day, visitors can also spend an afternoon at the Frelinghuysen Morris House & Studio, the 46-acre estate of the renowned American Abstract Artists George L.K. Morris and Suzy Frelinghuysen. For a historic night away, consider lodging at the Cornell Inn, which consists of three historic buildings, one of which dates back to 1777. As a plus, the inn serves a gourmet breakfast each morning, made with locally sourced and fresh ingredients!

Williamstown

Designated as a Massachusetts Cultural District, visitors can easily fill their itinerary with art and music during their vacation in Williamstown. Each summer, the town hosts its annual Williamstown Theatre Festival, which offers three weekends of chamber opera, classic American plays, choreography on ice, and other theatrical performances. When the festival is not going on, visitors can also attend a performance at the '62 Center for Theatre and Dance, which is part of Williams College, often offering low-cost tickets to community members and visitors. Located near Williams College and the Clark Art Institute, Maple Terrace offers guests acres of gardens, a swimming pool, and cozy rooms, perfect for a few nights away.

Wellfleet

With a mix of both freshwater and saltwater beaches, it is easy to spend your vacation in Wellfleet in the water. Travelers who prefer warmer waters and gentler waves will love the bayside beaches on Wellfleet Harbor. At Indian Neck and Powers Landing, for example, visitors can enjoy an afternoon of seashell hunting and swimming. Wellfleet’s biggest hidden gem, however, is its kettle ponds. These freshwater ponds, formed 15,000 years ago, have crystal clear water and often attract those wanting to swim and kayak. To be conveniently located near some of Wellfleet’s best beaches, visitors should spend the night at Endless Coast Boutique Hotel, which offers numerous amenities like an indoor pool, poolside deck, barbecue area, and fitness room.

Stockbridge

Stockbridge’s history dates back several centuries, incorporated as a town in 1739. Travelers can explore this history at the Stockbridge Library, which is one of the oldest libraries in western Massachusetts and is home to the Stockbridge Museum & Archives, which holds over 500 artifacts. After exploring the library, grab a bite at one of the town’s local restaurants, such as Once Upon A Table, which is set in a historic building and offers seasonal dishes. The Red Lion Inn is one of the town’s most iconic inns, with a history dating back to 1773. Today, travelers can stay in the inn, appreciating its antique-furnished rooms and enjoying amenities like an onsite gym and pool.

Northampton

Situated among farmland, forests, and the mountains of Western Massachusetts, Northampton has rightfully gained its nickname as “Paradise City.” Travelers can hop on their bike and enjoy a ride along the Manhan Rail Trail, a paved trail that extends from Northampton all the way to Easthampton. Afterwards, they can spend the afternoon at the Smith College Museum of Art, a museum with free admission that showcases over 27,000 pieces of art. Consider spending the night at Hotel Northampton, a historic hotel constructed in 1927 that features 106 elegantly decorated guestrooms. Amenities at the hotel include a fitness center, two restaurants, plush terry robes, and flat-screen TVs in each room!

Final Thoughts

Although everyone looks forward to going on vacation, vacation planning can often be intimidating. Choosing a destination and deciding which attractions to visit is not always easy. Luckily, this list of towns makes it a little bit easier. Whether you plan to spend your time on the beach, exploring museums, or relaxing by the hotel pool, these spots offer something that everyone in the family will enjoy. All that is left to do is pack your bags and start counting down the days!