Stroll through an acre of lush gardens at the Charles Hovey House (from $135), a bed-and-breakfast in downtown Gloucester. This Victorian home is adorned with plenty of antiques, but it stands out for its colorful, tidy rooms and a veranda that overlooks the harbor, an ideal viewing spot for fireworks over Labor Day weekend.
Make yourself at home in the lofty penthouse suite at Rocky Neck Accommodations (from $140), a short walk away from galleries, shops, and restaurants in the historic Rocky Neck Art Colony. The apartment's simple interior is reminiscent of a beach cottage, complete with a private deck overlooking the water, and a kitchenette where you can prepare freshly caught lobsters purchased from Turner's Seafood.
Let the sounds of the ocean lull you to sleep at the Bass Rocks Ocean Inn (from $269), named after the low rumbling of the Atlantic waves just across the street. The property features two newer buildings, the Oceanfront and Seaside Houses, but you'll find the most charm in the Stacy House (from $379), a turn-of-the-century home where the original Colonial Revival details have been preserved, but the second-floor suites feature modern amenities such as Jacuzzi tubs.