Newport, Rhode Island

Nearest major city: Boston, MA (approximately 1.5 hours)

With its Gilded Age mansions, breezy harbor views, and seemingly endless sailing opportunities, Newport blends classic New England beach-town charm with a distinctly polished, historic feel. Mornings are well spent strolling the 3.5-mile Cliff Walk with a coffee in hand—don’t miss the buzzy Nitro Bar—as the path winds along the shoreline past many of the city’s iconic mansions. Later, indulge in fresh seafood at local favorites like The Mooring Seafood Kitchen & Bar or Clarke Cooke House, people-watch alongBowen’s Wharf, or set out on a sunset sail through Newport Harbor. Afterward, head back to Wayfinder Newport, a stylish stay with retro-inspired interiors, a lively outdoor pool scene, and easy access to downtown so you’re never far from the water or the action. The hotel is also home to the aptly named Little Clam restaurant, a popular indoor-outdoor restaurant and bar known for seafood-forward fare, creative cocktails, and buzzy vibes.

Woodinville, Washington

Nearest major city: Seattle, WA (approximately 30 minutes)

Less than 30 minutes from Seattle, Woodinville offers an easy wine-country escape without the long drive. The area is home to more than 100 wineries and tasting rooms, giving the laid-back destination an approachable, small-town feel despite its proximity to the city. Spend the afternoon wine-tasting at hotspots like Château Ste. Michelle Winery and DeLille Cellars; alternatively, retreat to nature with a scenic bike ride along the Sammamish River Trail. In the center of it all is Willows Lodge, a cozy Pacific Northwest retreat with lodge-style interiors, luxe rooms and suites complete with soaking tubs and fireplaces, a spa, and easy access to many of Woodinville’s top wineries. The property is also home to the acclaimed farm-to-table restaurant, The Herbfarm, known for its multicourse tasting menus spotlighting Pacific Northwest ingredients.

Lake Arrowhead, California

Nearest major city: Los Angeles, CA (approximately 2 hours)

For Angelenos looking to escape the summer heat, Lake Arrowhead offers cooler temperatures, pine forests, and relaxed lake days just a couple of hours outside the city. Visitors can spend the day kayaking on the eponymous lake and hiking nearby trails in the San Bernardino Mountains before wandering the waterfront Lake Arrowhead Village. When hunger calls, grab brunch at Belgian Waffle Works, do a bit more shopping, and then make a beeline for Bin 189, the on-site restaurant at Lake Arrowhead Resort & Spa. The property also features a private lakeside beach, dock access, lake-view rooms, and a full-service spa, making it easy to settle in for the weekend.

Chatham, Massachusetts

Nearest major city: Boston, MA (approximately 2 hours)

Chatham captures the classic Cape Cod summer experience, complete with hydrangea-lined streets, weathered cedar-shingle homes, and seafood shacks. Travelers can bike along the Cape Cod Rail Trail, watch fishing boats roll into Chatham Fish Pier, browse the town’s independent shops and galleries, or grab lobster rolls from local favorite Chatham Pier Fish Market before catching sunset at Lighthouse Beach. Overlooking the Atlantic, Chatham Bars Inn remains one of the Cape’s most iconic stays, pairing classic New England charm and luxe accommodations spanning contemporary rooms to adults-only spa suites and freestanding cottages. Add in resort-style amenities—including a private beach, boating and sailing excursions, non-motorized water sports, a spa, pools, tennis, and swanking drinking and dining options—and you’ve got a great getaway.

St. Michaels, Maryland

Nearest major city: Washington, D.C. (approximately 2 hours)

Located along Maryland’s Eastern Shore, St. Michaels is one of the easiest waterfront getaways from D.C. The town is best known for its sailing culture, crab houses, and laid-back coastal atmosphere, where seafood spots like The Crab Claw serve fresh-shucked oysters and crispy crab cakes well into the evening. Downtown, there are local staples like Book Hounds and Blue Heron Coffee, plus easy access to the Chesapeake Bay Maritime Museum. A stay at the Inn at Perry Cabin — with its manicured waterfront grounds, classic coastal interiors, sailboat excursions, a pool, and a tranquil spa — is a must.

Bonus: Bermuda

Nearest major city: New York City (about 1.5 hours via plane)

Bermuda feels much farther away than it actually is, with direct flights from NYC making it possible to swap city streets for pink-sand beaches in just a couple of hours—technically making it closer than the Hamptons for many travelers. Beyond the pristine stretches of sand, visitors can explore the almost otherworldly Crystal Caves, cliffside walking trails, and the colorful streets of Hamilton and St. George’s. Before or after, be sure to indulge in one of Bermuda’s iconic fish sandwiches at local spots like Art Mel’s Spicy Dicy or Mama Mia's. Set on a secluded peninsula, Cambridge Beaches Resort & Spa offers not one but four (!) private beaches—that is, in addition to two coves, waterfront cottages, and some of the island’s best sunset views. Don't miss Breezes, the resort’s open-air beachfront bar and restaurant, popular for sunset cocktails right on the water.

Explore more resorts and hotels across the Benchmark Resorts & Hotels portfolio, a collection of distinct, independent properties by Pyramid Global Hospitality. Located in diverse destinations across the globe, Benchmark’s resorts and hotels reimagine immersive travel, inspiring guests to create memories born from meaningful exploration, authentic moments, and innovative experiences – no matter the occasion. Benchmark guests can earn complimentary gift cards, on-property perks, and destination experiences through the collection’s signature Mosaic Rewards program.