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We've compiled the best of the best in Side Trips from Boston - browse our top choices for the top things to see or do during your stay.
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.
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.
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.
