Labor Day weekend, the last hurrah of the summer, is one of the most popular times of the year for travel. The three-day weekend makes it convenient for many people to take trips to visit family, friends or enjoy a final summer getaway. Airports and highways are expected to be crowded as a result.
The northeast offers a smorgasbord of options for travelers, including a tour of sprawling vineyards, climbing to the top of historic lighthouses or enjoying a classic yacht regatta. No matter your preference, you won’t be shortchanged by a Labor Day visit to the northeast. Travelers would be wise to consider these charming accommodations:
Island House Hotel – Newport, Rhode Island
Ideally located in the center of Newport, Rhode Island, Island House Newport blends laid-back coastal elegance with modern comfort. Thoughtfully designed for both short and extended stays, the spacious suites feature full kitchens, multiple bedroom configurations and stylish living areas, making it an ideal retreat for couples, families or groups. Guests can take advantage of the property’s complimentary bikes, enjoy freshly brewed, custom Island House coffee blend, unwind on the outdoor patio and experience the vibrant local culture with weekly farmer’s markets just steps away. Celebrate Labor Day Weekend in style by sipping wine at Newport Vineyards, watching the 46th Annual Newport Classic Yacht Regatta or attending the Newport International Polo Series.
The Ranch Hudson Valley – Sloatsburg, New York
Located on a historic, lakefront estate that stretches 200 forested acres in the lower Hudson Valley, less than an hour from New York City, The Ranch Hudson Valley is a respite for revitalizing the body and mind. With 3-night and 4-night guided programs, The Ranch Malibu’s sister property is perfect for a long weekend wellness getaway. Each day features signature mountain hikes, naptime, strength training classes, restorative yoga, deep tissue massage and organic, plant-based meals. Guests stay in one of 26 private rooms that showcase the property’s exquisite original architectural details. Guests can also immerse themselves in the picturesque views of the tranquil lake and expansive grounds throughout the estate. The property includes an elegant living room, a light-filled dining room, game room, a 5,000 square foot Solarium, a spa, indoor and outdoor pools, hot and cold plunges and a spacious gym – formerly the ballroom – offering ample space for afternoon fitness and yoga classes.
Canoe Place Inn & Cottages – Hampton Bays, New York
Known as America’s oldest inn, Canoe Place Inn has been reimagined as a luxury escape in the Hamptons, blending centuries of history with modern elegance. Set on six landscaped acres, the restored landmark features 20 thoughtfully designed accommodations and five private cottages, a full-service spa, pool, premier event venues and seasonal coastal cuisine at Good Ground Tavern, now helmed by rising star Chef Edwin “Eddie” Alvarracín.
Sound View Greenport – Greenport, New York
Sound View Greenport, set on 14 acres of private waterfront, is a beautifully restored property that captures the essence of coastal charm and laid-back luxury. Guests can unwind with sweeping views of the Sound, take part in hands-on art classes, sip their way through local wine tastings, or join chef-led tours of nearby historic farms. Whether you’re craving calm or connection, Sound View is the perfect place to recharge before fall. Cap off your day with a dinner at The Halyard, the hotel’s acclaimed restaurant featuring locally sourced ingredients and award-winning chefs.
Harbor Front Inn – Greenport, New York
Just a quick trip from New York City, the Harbor Front Inn is perfectly situated in the center of Greenport Village, making it an ideal Labor Day weekend escape. Guests can spend the long weekend exploring local art galleries, dining at homegrown restaurants, browsing charming boutiques or even distilling their own spirits at Matchbook Distilling. Whether you’re looking to relax or explore, Harbor Front Inn is the perfect home base for a memorable end-of-summer getaway.
Urban Cowboy Lodge & Resort – Big Indian, New York
A rustic-luxury retreat in the Catskills, the Urban Cowboy Lodge & Resort recently expanded from 68 to 120 acres with the addition of the historic Slide Mountain Inn. The resort features vintage cabins, a bowling alley, soaking tubs, a sauna, hiking trails and locally inspired dining, all wrapped in the brand’s signature design sensibility.
The Docent’s Collection – Portland, Maine
Set along the scenic coastline of southern Maine, Portland, The Docent’s Collection is the perfect destination for a coastal escape, offering a charming mix of history, culture and award-winning cuisine. The property offers luxurious apartment-style lofts just steps from vibrant art, charming boutiques and a nationally acclaimed culinary scene. With studio, one, two and three-bedroom options, each residence features high-end furnishings, a fully equipped kitchen, spa-like bathrooms and spacious rooms ideal for groups, couples or solo travelers. Guests can unwind in a space that feels like their own and seamlessly combines modern design with the city’s historic charm, offering the perfect retreat after a day of exploring. Select accommodations also offer in-unit washers and dryers, fireplaces and curated local artwork that reflect Portland’s rich cultural heritage.