13 Best Hotels in Side Trips from Boston, Massachusetts

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. 

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.

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.

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. Rooms are equipped with coffee makers and portable air conditioning units. Cape Ann SUP rents paddleboards and surfboards at the property from Memorial Day through Labor Day.

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.

This elegant full-service historic hotel celebrates its 100th anniversary in 2025 and is named for the town's most famous writer. It's within walking distance of the town common, museums, shops, 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.

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. Guests receive complimentary breakfast on weekdays. 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. Minimum nights may be required.

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.

The 11-room Merchant is an intimate, design-forward Lark Hotel property in the heart of Salem's historic district. Just blocks from the Salem Harbor, the Merchant piles on the amenities, like the complimentary grab-and-go breakfast; free coffee, water, fruits, and snacks all day in the lobby; and great discounts at local shops and attractions. Rooms have everything from Apple TV and gas fireplaces to waffle kimono robes. Reserve the George Washington King Deluxe room; it's the same room where the newly elected president slept during his visit to Salem in 1789.