Prouts Neck, Maine
On a craggy peninsula just south of Portland, the gray-shingled 1878 Black Point Inn (doubles from $480, including breakfast and dinner) occupies a prime waterfront location. The owners have updated the public spaces and 25 nautical-themed rooms. Now you’ll find a geothermally heated sauna and outdoor pool, Frette linens, and flat-screen televisions. Watch sailboats from a wicker rocker on the porch, stroll the sandy beaches (a Down East rarity), or hike the Cliff Walk, a nearby trail where artist Winslow Homer painted scenes of the coast.
Don’t Miss: Picnicking at Ferry Beach State Park. Pick up supplies—country pâtés; Fern Hill Farm goat cheese; Pink Lady apples—at the Cheese Iron, in Scarborough.
Courtesy of The Claremont
Southwest Harbor, Maine
Great Value Down a winding road amid the pine trees on Mount Desert Island, the 19th-century Claremont Hotel (doubles from $205) looks like a country estate—it’s easy to picture the blue-blooded Rockefellers and Morgans (many of whom still have houses in the area) sipping gin on the wraparound porch and playing croquet on the lawn. The 24 rooms are traditional but polished, eschewing lacy bedspreads for crisp linens and bleached-wood furnishings. Best of all is the view of Acadia National Park from the wooden dock at the edge of Somes Sound, considered the United States’ only fjord. At night, there’s no better place to stargaze.
Don’t Miss: A fisherman’s lunch of chowder and fried clams at the no-frills Docksider (lunch for two $32), in Northeast Harbor.
Courtesy of Hob Knob
Martha’s Vineyard, Massachusetts
A short walk from the center of Edgartown, the Hob Knob (doubles from $395) has the notion of coastal living down pat. Inside the three-story Gothic Revival building are 17 light-filled rooms dressed in toiles and stripes, each grounded by an English antique or two. Breakfast is made to order from local farm ingredients, including homemade fig preserves, and served in two sunny rooms, one with Currier & Ives blue-patterned plates nearly covering the walls from floor to ceiling. Book a treatment in the small spa, bike the island’s well-maintained trails, or go fishing in the inn’s Boston Whaler.
Don’t Miss: Clamming or oystering like a native—the hotel will give you the tools and know-how to bring home the seafood, then serve it up back at the inn.
Courtesy of The Cottages At The Boat Basin
High above the tide mark on private docks along Nantucket’s harborfront, you’ll find the Cottages & Lofts at the Boat Basin (doubles from $490). Most of the 24 saltbox bungalows have balconies or terraces with views of the marina. Guest rooms are decked out in red, white, and marine blue; a concierge will stock the kitchen with groceries and arrange for a picnic at nearby Surfside Beach. It’s the perfect jumping-off point for exploring the miles of hiking paths that weave around cranberry bogs and grassy dunes.
Don’t Miss: Shopping for delicate straw summer hats at Peter Beaton Studio, where each style is named after one of the island’s romantic spots.
Courtesy of Blue, the Inn on the Beach
Plum Island, Massachusetts
Unlike Martha’s Vineyard and Nantucket, this 11-mile-long barrier isle off the state’s North Shore has remained relatively undiscovered. Which is why the opening of Blue, the Inn on the Beach (doubles from $345, including breakfast) two years ago was a pleasant surprise. Hotels like the Delano, on South Beach, served as the inspiration for Blue, with its modern aesthetic. The eight suites and six cottages are connected by mosaic-tiled walkways, while the stark white-on-white rooms have touches of blue throughout—a throw, a vase, wineglasses, flip-flops.
Don’t Miss: Scoping out the marshes and thickets of the island’s 4,600-acre wildlife refuge with one of the hotel’s bicycles.
Great Value Close to the tip of Cape Cod, the rose-covered Red Inn (doubles from $140, including breakfast) provides a respite from the parade of characters that transforms much of Commercial Street into an open-air theater all summer long. Here, the entertainment is the dance of light over the harbor, which you can see from each of the eight aptly named rooms (Sunset View; Cape Light). Built in 1805 by a ship’s captain for his wife, this sweet little hotel also has a popular dining room that serves fish caught just offshore.
Don’t Miss: The Cranberry Bog Trail, in nearby Truro, which passes through the woods and over high dunes to deserted Ballston Beach.
Courtesy of Virginia Hotel
Cape May, New Jersey
With its Victorian-era houses, 19th-century working trolley, and chiming church bells, this village at the southernmost tip of the state is postcard-perfect. On its main road, you’ll find the Virginia Hotel (doubles from $349, including breakfast), a contemporary 24-room retreat with sleek cherry-red sofas and a baby grand piano in the lobby. Upstairs, the bedrooms are outfitted with Belgian linens and bathrooms have a trio of showerheads. At the Ebbitt Room restaurant, leather banquettes line the minimal space, where chef Lucas Manteca serves native oysters topped with champagne granita and trout caviar.
Don’t Miss: A trip to Bay Springs Farm Alpacas, run by the Nestle family. Here, you can visit a herd of alpacas and buy homespun scarves, shawls, and sweaters.
Southold, New York
A two-hour drive from New York City, North Fork Table & Inn (doubles from $275, including breakfast) is owned by a pair of Manhattan culinary stars, chef Gerry Hayden (from Aureole) and his wife, James Beard Award–winning pastry chef Claudia Fleming (formerly of Gramercy Tavern). The duo turns out New American dishes, such as raw hamachi and seared Hudson Valley foie gras. Come for the food, but stay in one of the four cozy rooms, which have cherrywood sleigh beds and exposed red brick. You’ll wake up to the best blueberry and apricot scones you’ve ever tried.
Don’t Miss: The Tasting Room, a tin-ceilinged wine boutique nearby with samples from 10 North Fork vineyards.
Courtesy of Hotel Chesterfield
Great Value You may not think of Stamford as the ideal summer getaway, but the Hotel Chesterfield (doubles from $239), set in a well-heeled residential enclave, is just a stone’s throw away from a private beach. You’ll find a mix of old and new in the nine rooms: flat-screen TV’s are propped on hand-carved mantels; antique desks are stacked with Assouline art books. Windows overlook Dutch Colonial manses, Queen Anne–style residences, and the broad oak trees lining Westcott Cove.
Don’t Miss: The soft-serve at Sunny Daes (ice cream for two $6), a pink-and-teal ice cream stand across from 79-acre Cummings Park.
Courtesy of Inn at Stonington
Great Value Occupying a mile-long peninsula, this village of beautifully preserved 18th- and 19th-century houses is not just a time capsule, it’s home to a commercial fishing fleet. At the Inn at Stonington (doubles from $190, including breakfast), you’ll find luxurious amenities (Frette linens and robes; whirlpools in 16 of the 18 rooms), vintage maritime prints, and modern touches (Asian-themed room No. 7, with its balcony overlooking the harbor, is a guest favorite). A five-minute walk leads to tiny Dubois Beach, where guests can go kayaking or simply take in the view.
Don’t Miss: Nearby Mystic Seaport, a waterfront museum of historic whaling ships that you can climb aboard and explore.