15 Safe Labor Day Luxury Getaways in New York and New England

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Labor Day is the second-deadliest weekend to drive in America, behind only July 4, according to a new study of recent data from the NHTSA, FBI and Census Bureau. For luxury travelers driving to their last-minute Labor Day getaways, it’s important to be smart about where you go.

The safest state to drive might come as a surprise: New York, with low rates of motor vehicle fatalities (5.56 per 100,000 residents), DUI arrests (69.39 per 100,000), and speeding-related fatal crashes (1.59 per 100,000). The rest of New England dominates the study’s safest states. Massachusetts (No. 2) pairs 5.16 fatalities per 100,000 with one of the lowest speeding fatal crash rates (1.50). Rhode Island (No. 6) has the lowest fatality rate in the U.S. at 4.67 per 100,000. New Hampshire (No. 9) and Connecticut (No. 10) round out the Top 10.

If you want to hit the road this Labor Day, stay safe, and spend some money, escape the traffic by visiting these 15 luxury destination properties in New York and New England.

New York Luxury Travel Getaways Labor Day Weekend

Chatwal Lodge – The Catskills

One hundred miles west of Manhattan sits The Chatwal Lodge, a Hyatt Unbound property located where the green canopy of the Catskills meets the shore of the Toronto Reservoir. Groups that need some room to spread out will love the 2,800-square-foot stone cottage, which starts at $2,351 per night for Labor Day weekend. The property’s elevated treehouses are half the size but offer a unique view, floating 15 feet above the ground among the oaks, maples and birches. All guests have the opportunity to explore The Chapin Estate, part of the 18,000‑acre Chapin Park, a private wildlife reserve established by entrepreneur Chester Chapin in 1891. The Chatwal, which feels as new as it did upon opening in 2022, offers the perfect contrast to the old-growth forest.

Gurney’s Montauk Resort & Seawater Spa – Montauk, NY

Perched on a bluff overlooking the Atlantic Ocean, Gurney’s Montauk Resort is going big for Labor Day with sunset bonfires, Gurney’s Kids Club, the Sound Waves Music Series, The Summer Fitness Series, and Dolce & Gabbana’s pop-up experience. The slate of features caters to a broad spectrum of luxury travelers who will be hard-pressed to find a bigger and better beach at any price point in The Hamptons. Availability for the Ocean View suites and cottages is limited during Labor Day weekend, when rates start at $2,237 per night, but all guests have direct access to Gurney’s 2,000-foot long private sand beach. Visit Gigi’s Montauk for oceanfront dining or Dune Cafe & Lounge for breakfast before soaking up the sun while it still lasts.

The Beekman Arms – Rhinebeck, NY

In 1704, William Traphagen founded the Traphagen Tavern at a crossroads in what would become Rhinebeck, NY. In 1766, the Beekman Arms building was added to the tavern structure and has been in continuous operation ever since — making it, by many accounts, America’s oldest continuously operated inn. Historical figures from George Washington and Alexander Hamilton to Neil Armstrong and Oprah Winfrey have been said to stay at the property, which counts 73 rooms including those in the property’s historic buildings and guesthouses, outfitted with modern amenities. Come for the history, stay for the Bottomless Mimosa brunch buffet every Sunday.

Rhode Island Luxury Travel Getaways Labor Day Weekend

The Chanler at Cliff Walk – Newport, RI

The Chanler at Cliff Walk was completed in 1873 as the summer residence of New York Congressman John Winthrop Chanler, who hosted Theodore Roosevelt and Henry Wadsworth Longfellow before the property was converted to a hotel after World War II. Its 20 uniquely themed guest rooms start at $1,753 for Labor Day weekend. Each is individually decorated with period-specific furnishings — Victorian, Renaissance, French, etc. The Forbes five-star hotel features an in-house restaurant, Cara, with views of The Cliff Walk and the Atlantic shoreline.

The Ocean House – Watch Hill, RI

The Ocean House in Watch Hill opened in 1868, just after the Civil War, and quickly became a premier summer retreat for New England’s elite. After decades of operation, the original building closed in 2003 due to code and structural issues. It was demolished in 2005, and a newly reconstructed facility faithfully replicated the original when it opened in 2010. It still exudes Victorian grandiosity while boasting amenities like the 12,000-square-foot Ocean & Harvest Spa, and an indoor saltwater pool. The hotel is booked for Labor Day weekend but COAST, the resort’s fine-dining restaurant, serves up a seasonal prix fixe menu that changes daily.

The Preserve Sporting Club & Resort – Richmond, RI

The Preserve, a sweeping, 3,500-acre luxury retreat in Richmond, blends immersive outdoor adventure with high-end accommodations and a 12,000-square-foot spa. Rhode Island’s lone golf resort is a favorite of New Englanders of every handicap; equestrian training stables and an indoor shooting range beckon a variety of sportsmen in the summer as well. Accommodations start at $1,055 for Labor Day Weekend.

The Breakers – Newport, RI

While not available for overnight stays, The Breakers is a must-see during any Newport visit. Commissioned by Cornelius Vanderbilt II in 1893 and designed by Richard Morris Hunt, the Italian-Renaissance palazzo stands as a monument to the lifestyle of America’s 19th-century one percent. Rooms shimmer with gold leaf, marble, and Murano glass, spread across 70 oceanfront acres. If you’re a fan of HBO’s The Gilded Age, you’ll find the real thing here — This is Newport’s living set piece from that extravagant era. For those in or passing through New England, a visit to The Breakers is a glorious and decidedly worth-it day trip.

Connecticut Luxury Travel Getaways Labor Day Weekend

Mayflower Inn & Spa – Washington, CT

A country inn located less than two hours from New York City in Washington, Connecticut, the Mayflower Inn & Spa transports guests back across the Atlantic via an English country house and three standalone cottages. Former President Bill Clinton is among the famous guests at the property, which was originally built as a 19th-century schoolhouse. For Labor Day, it’s offering a slate of family-friendly activities: live music, house-made ice cream scoops, and wine tasting. Rooms start at $1,739.

Delamar Mystic – Mystic, CT

Charles Mallory was an integral figure in the development of the shipbuilding town of Mystic, Conn. in the 19th century. More than two centuries later, his namesake great-great-great-grandson founded the Delamar Mystic, a boutique hotel featuring 31 elegantly appointed waterfront rooms and suites, all with floor-to-ceiling windows showcasing Mystic River views. The aesthetic speaks to the locale’s history, and the 1,660-square-foot Corinthian Cottage — ideal for long-term or private stays — spreads it out over two stories with two king bedrooms, a fireplace, soaking tub, kitchenette, and terrace. Though rooms are booked through Labor Day, the in-house La Plage Restaurant & Oyster Bar serves up freshly caught seafood all weekend.

Winvian – Morris, CT

Winvian began its existence as a farmhouse in the 18th century and maintains the farm-to-table tradition to this day with several gardens and greenhouses on-site. Executive Chef Chris Eddy’s restaurant is just as famous as Winvian’s 18 uniquely themed cottages and one master suite (the Hadley Suite, located in the historic Seth Bird House). Each cottage is architecturally distinct, designed by different architects, to reflect Connecticut’s landscapes and lore. Rooms are scarce for Labor Day weekend, starting at $1,340.

Litchfield Inn – Litchfield, CT

Blending vintage country charm with modern sophistication, the Litchfield Inn offers 32 guest rooms across 10 acres of beautifully landscaped grounds. Its 12 bespoke themed rooms (up to $359/night for Labor Day weekend) feature detail-oriented design, while the 20 classic rooms reflect the simple beauty of the Connecticut countryside outdoors. As a full-service boutique hotel, the Litchfield Inn includes common guest lounges, a fitness center, free breakfast, and grand spaces for events and weddings. Litchfield is known as an exclusive enclave celebrated for its colonial charm and quiet luxury, perfect for enjoying Labor Day weekend at your own pace.

Massachusetts Luxury Travel Getaways Labor Day Weekend

Miraval Berkshires Resort and Spa – Lenox, MA

The Wyndhurst Mansion at the Miraval Berkshires Resort and Spa is a stately tribute to Gilded Age opulence, constructed in 1894. It was absorbed by the wellness-focused Miraval chain in 2020, joining the properties in Tucson and Austin, with the addition of free-standing cottage and carriage houses and a modern wellness campus adjacent to the mansion. Like its sister properties, the Miraval Berkshires offers a $175 nightly resort credit for spa treatments and private sessions. Walk the historic 18-hole golf course for sweeping views of the rolling New England countryside. Labor Day weekend accommodations start at $957, but note that guests under 18 are not allowed.

Four Seasons Hotel Boston – Boston, MA

Staying at the Four Seasons Hotel Boston is a front-row seat to the city’s best-dressed seasons: In winter, the lobby hums with the esteem of its neighboring brownstones of Beacon Hill; oysters crowned with caviar at Coterie are served to the chic skaters fresh off Frog Pond; and a Teddy Bear Breakfast, charming enough for both the stroller VIPs and their mimosa-sipping parents. Boston’s rich history is best taken by wandering through Boston’s cobbled history or a museum detour worthy of a long weekend. Start your Four Seasons Boston journey now, return again later in the season. Rates Labor Day weekend start at $992 per night.

Mandarin Oriental Boston – Boston, MA

The Royal Suite at the Mandarin Oriental, Boston (not pictured here) is the pinnacle of luxury overlooking Boston’s Back Bay neighborhood. For $17,468 a night, you get floor-to-ceiling windows, chandeliers, a marble bathroom and kitchenette — all within walking distance of the Charles River. The property, which opened in 2008, is considered a go-to for celebrities when staying in Boston. It features the spacious bathrooms and elevated decor associated with all the Mandarin Oriental properties. The in-house Gordon Ramsay restaurant serves hot meals starting with breakfast at 6:30 a.m.

Canyon Ranch Lenox – Lenox, MA

The only Canyon Ranch property in New England lies in Lenox, on the western edge of Massachusetts in the Berkshires. The resort centers around the Gilded Age Bellefontaine Mansion (completed as a private residence in 1898), while the wellness-focused chain arrived in 1989. Included in your stay: unlimited meals and snacks crafted with a healthy lifestyle in mind, spa services that include body composition screening, a VO2 Max assessment, hydration testing and exercise assessment to work out smarter. Rooms are available for $1,500 per night on Labor Day weekend.