The Many Charms of a Small Town USA Getaway

Just 90 minutes north of Boston, Kennebunkport was a shipbuilding mecca that’s now a coastal getaway with plenty of antique charm. White Barn Inn is a beloved local landmark dating back 150 years. This hideaway is renowned for its award-winning cuisine and offers the choice between guestrooms, suites and standalone cottages with views of the river. Ice-cream by the pool, cooking classes with the chef, visits to local farms, a day at sea—there are limitless activities on and off property.

Aptly coined “Florida’s Village by the Sea,” Delray Beach is a small town with a big city personality. Lazy days on the sand, shopping on downtown’s Atlantic Avenue, the Pineapple Grove Arts District—this intimate town has it all. Perfectly capturing the city’s coastal cool vibe is The Ray Hotel, an architectural icon decked out in “tropical modern” style, large-scale sculptures and immersive art installations. Soak up those Florida rays on the sprawling rooftop deck, complete with pool, lounge and restaurant.

The town of Bedford is just a short drive from the Manchester-Boston Regional Airport yet feels like a world away. It’s where sophisticated New England style seamlessly blends in with nature. Bedford Village Inn sits on a 10-acre estate that was once a working farm, and nowadays is a popular venue for weddings and special occasions. The rooms still retain their rustic charm, the kitchen sources from local farms and the North Atlantic sea, and its gardens are adorned in wisteria and fountains.

Old Town Key West offers the vibrancy of a tourist destination with the laid-back vibe of a historic small town. Nearby Duval Street, tucked away from the action, Kimpton Winslow’s Bungalows is an artful and bohemian hotel campus named after the famous painter and summer resident, Winslow Homer. Its brick walkways lead to three pools, an outdoor bar and accommodations spanning several architectural styles—once home to an assortment of characters spanning an army officer to a circus performer.

The historic Village of Manchester, a photogenic town of marble sidewalks, locally owned shops and a church steeple, backdropped by a quintessentially Vermont landscape of country lanes, covered bridges and the misty Green Mountains, seems straight out of a movie set. Fitting right into the heart of the village is the Kimpton Taconic Hotel. Featuring traditional clapboard architecture and a grand front porch, this free-spirted hotel was inspired by the leisure inns of the late 19th century.

Just across Chesapeake Bay, St. Michaels is a tranquil, storybook town nestled on Maryland’s Eastern Shore. On its waterfront is the Inn at Perry Cabin, a colonial turned contemporary home set on acres of gardens flowing down to the harbor. It’s a romantic glimpse into the town’s storied history, where time stands still and days are spent watching the calm waters. Here, indulge in sea-to-table cuisine, a round of golf and sailing lessons, or pedal into the town center to tour museums, shops and galleries.

A seaside town of cobblestoned streets, harborside shops and pre-Civil War architecture, Nantucket has been a premier resort destination for almost a century. Among its most iconic landmarks is White Elephant; originally rustic cottages from the 1920s, this resort has grown to include rooms and suites, garden cottages, luxurious residences and downtown lofts. On property is an outdoor pool and a steak and seafood grill, while just steps away is the beach, lighthouse and Nantucket Town.

Rhode Island, famed for its miles of sandy coast, ideal conditions for sailing and Gilded Age mansions, has long been the summer vacation spot for the genteel. Originally opened in 1868, Ocean House has been meticulously restored to honor its distinguished past. Today, it’s as elegant as ever, featuring turn-of-the-century décor, restaurants focused on farm-to-table fare and a spa overlooking the Atlantic. The hotel offers a private beach and art and cultural programs. Guests can also go yachting and exploring the island’s museums, galleries and antique stores.

A seaside town with a lively Main Street and sandy beaches, Chatham is a Cape Cod escape with lots of New England charm and a long list of things to do. Chatham Bars Inn claims to be the most beautiful address on the cape and it’s no wonder why; this property on a private quarter-mile beach spans a historic inn, spa suites and cottages looking out to fishing boats and seals sunbathing on the sandbanks. It’s luxurious with a pool, outdoor spa cabanas and waterfront dining, while a short drive away is the hotel’s farm and the town.

Healdsburg is the small town sister to ever-popular Napa, centered around a historic town plaza lively with shops, restaurants, galleries and tasting rooms. Just off the plaza is the Harmon Guest House, named after the town’s pioneering founder Harmon Heald. This architecturally stunning hotel was designed to foster community, featuring creative public spaces, locally sourced art and fixtures, and unique, light-filled rooms meant for bringing people together. There’s also the rooftop terrace for gathering and indulging in the views.