10 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.

Built in 1845, this Greek Revival house is a comfortable bed-and-breakfast near all the historic attractions. With high ceilings and marble fireplaces, the three guest rooms are each different, decorated with bold colors and contemporary flair.

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.

Walk to the waterfront and downtown Plymouth from this clean, family-friendly motel. Rooms, some with balconies, are minimalist, with white walls, dark carpeted floors, and contemporary furniture. Amenities in rooms include free high-speed wireless internet, a mini-refrigerator and microwave. A heated outdoor pool will keep the kids happy.

On the sands of Long Beach, this three-story, shingled motel, open year-round, has no-frills rooms except for the balconies and ocean views. Half of them have well-furnished kitchenettes. The Honeymoon Suite is pricier but has a full kitchen, fireplace, whirlpool bath, king-size bed, and private balcony. Free coffee and pastries are available in the lobby every morning. Cape Ann SUP rents paddleboards and surfboards at the property from Memorial Day through Labor Day.

This year-round hotel less than a mile from downtown Gloucester comes alive in summer with an on-site restaurant and deep-sea fishing excursions. The rooms—comfortably decorated, but not fancy—all have balconies and water views. The hotel's seasonal outdoor bar and dining area is a great place for an afternoon cocktail or light fare right on the water. If you're looking for a quieter stay, ask for a room in the middle of the building.

Housed in a pair of adjoining 18th-century mansions in the heart of Old Town Marblehead, this elegant inn, which is now honored as one of the Distinguished Inns of New England, features many rooms with canopy beds, brick fireplaces, and jetted spa tubs. A soaring ceiling on the top floor reveals the original post-and-beam construction. Rates include full breakfast buffet and free parking. The inn can also accommodate intimate weddings and parties of up to 40 guests.

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.

Elegantly restored, this full-service historic hotel celebrates the town's most famous writer and is within walking distance of the town common, museums, and waterfront. The tastefully decorated rooms include amenities like free Wi-Fi and windows that open; many rooms have great views of Salem Common. A full-service restaurant and a cozy tavern are also on-site.

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.