4 Best Hotels in Side Trips from Boston, Massachusetts

Just a minute's walk from both the center of Rockport and the train station, this 1851 inn sits in a prime location. The sizable and beautifully decorated rooms have their share of antiques and local seascape paintings, as well as pine floors and large, private marble bathrooms; the large Dog Watch suite contains a luxe king bed, Oriental rugs, and has a comfortable seating area. In the third-floor suite, with its own entrance, huge windows look out over the rooftops to the sea. In the afternoon, sweet treats are set out for guests. Children age 12 and older are welcome.

Near the end of Bearskin Neck, this small brick-and-shingle motel offers guests the best of both worlds: beautiful, oceanfront rooms, as well as easy access to shopping and restaurants. The rooms are simply appointed and furnished with comfortable wooden furniture and white chenille bedspreads. At night, you can go to sleep listening to the waves, and, during the day, you can walk just five minutes to Front Beach, or sun yourself on the motel's large deck. Complimentary services include Wi-Fi, air-conditioning, coffee and tea in the main office, and parking. In high season, there may be minimum-stay requirements.

An elegant retreat overlooking the ocean, this beautifully restored historic property where, yes, Ralph Waldo Emerson once stayed, dates back 150 years. Well-appointed rooms (make sure to request an ocean front room) are comfortable with luxurious bedding and amenities. The '20s themed lounge will make you want to dress up and order a fancy drink, while breakfast on the expansive porch will have you linger over coffee. Don't skip the walking path outside the inn along the Atlantic.

Within walking range of shops, restaurants, and beaches, this historic inn, sister property of Addison Choate, was named for a member of Hannah Jumper's "Hatchet Gang," teetotalers who smashed up the town's liquor stores in 1856 and turned Rockport into the dry town it remained until as recently as 2008. Renovations in 2021 upgraded the property without erasing any of the charm. Extras include bike rentals and even pre-stocked fridges.