7 Best Hotels in Side Trips from Boston, Massachusetts

Built in 1845, this Greek Revival house is a luxurious bed-and-breakfast option near all the historic attractions. With high ceilings and marble fireplaces, the two guest rooms are each different, decorated with bold colors and contemporary flair. Advance planning is required to stay here as rooms can book up a year out.

With original woodwork and cozy fireplaces, this restored 1900 Victorian inn perfectly captures the Cape Ann aesthetic. Castle Manor overlooks the peaceful Annisquam River (it's actually a saltwater estuary). In addition, the owners have a pet-friendly motor lodge with another 16 rooms. The tiny Half Moon Beach at Stage Fort Park is just a three-minute drive down the road. Breakfast, available in the Bistro, is offered Wednesday through Sunday, but is not included with the room price.

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.

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. 

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.

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.

Luxurious accommodations spread out over three historic buildings—the Main House, Mulliken House, and the Barn—are well-appointed with bright, fun decor and amenities like Frette linens. Some rooms have rain showers or plunge baths in marble bathrooms. Guests can request the use of the inn's Volvo to explore. Upscale American fare is offered at the Town Meeting Bistro, and Saturday high tea or Sunday brunch make the weekend extra special. Snacks in the guest room and continental breakfast are included.