From Laid-Back To Lavish, Here Are The Best Last-Minute Labor Day Getaways To Book This Year

If deciding on a LD weekend travel destination is a struggle, we’ve just made the decision that much easier for you. Here are five amazing places to celebrate the end of summer over Labor Day 2019. 

Nantucket, MA

Nantucket Photo Credit: GagliardiPhotography

Head to the teensy, tiny preppy haven that is Nantucket for your Labor Day holiday. This picture-perfect paradise, located just 30 miles off the coast of Cape Cod, is totally consolidated (it’s three miles wide and 15 miles long), meaning, that everything you want is in one place. Expect unique boutiques (the only chain is Ralph Lauren), darling seafood eateries and beaches for days.

Stay at: The Wauwinet

WauwinetPhoto Credit: Nantucket Island Resorts

The Wauwinet, Nantucket’s only Relais & Châteaux property, underwent a massive multi-million dollar renovation and restoration of its lobby, library, and 32 guestrooms and cottages earlier this year, which is reason enough to stay.  As part of the overhaul, the hotel collaborated with Serena & Lily to re-design the property’s three-bedroom Anchorage House with the brand’s signature coastal prints and furniture. Even better: guests who book the unit will receive keys to 2019 BMW 760L SUV vehicle for the duration of their stay. The hotel is also home to TOPPER’S, the island’s only AAA Five Diamond Award winning restaurant, which has earned Wine Spectator’s Grand Award for 23 consecutive years.

120 Wauwinet Rd, Nantucket, MA 02584

Hilton Head, SC

Hilton HeadPhoto Credit: MargaretW/

Life is a beach on Hilton Head Island, where Labor Day travelers can indulge in all the fun and sun they can handle. Summertime may be crowded, but it’s also the perfect place for that 90-degree beach weather. It’s no wonder this South Carolina locale has been named America’s best island for four years in a row.

Stay at: Montage Palmetto Bluff

Montage Palmetto BluffPhoto Credit: Stacie Flinner

With 18 miles in between, Montage Palmetto Bluff is just far enough away from Hilton Head that you can still enjoy all the beach destination offers without fully submerging yourself in the crowd. This 5-star antebellum property has its own goings on for the Labor Day holiday, however, so you’ll never feel far removed from any action. During the holiday, there’s everything from a fishing tournament, to kite decorating to a backyard-style Southern BBQ to keep yourself entertained.

477 Mt Pelia Rd, Bluffton, SC 29910

Sonoma, CA

SonomaPhoto Credit: jbtphotos/

Its sleepy, almost laid-back, cool kid vibe makes Sonoma a must for us any time of year, but Labor Day is particularly special thanks to Taste of Sonoma, a glorious festival showcasing the best of the area. Sip and savor to your heart’s delight thanks to participating wineries like Ridge, La Crema and Silver Oak Cellars, as well as nibbles provided by the likes of Tsar Nicoulai Caviar and Imagination on Fire.

Stay at: Hotel Fairmont Mission Inn & Spa

Fairmont Mission InnPhoto Credit: Fairmont Mission Inn

If relaxation with wine in hand is the name of the game, then stay at the glorious Fairmont Mission Inn & Spa, where literally everything you could ever ask for is in offer. Not only is it one of the only luxury spa resorts in America to have its own source of thermal water, but it also has a 75-year-old private 18-hole golf course and a 40,000 square foot spa. And did we mention wine?

100 Boyes Blvd, Sonoma, CA 95476

Las Vegas, NV

Las VegasPhoto Credit: f11photo/Shutterstock

There is no bigger party anywhere in America than Las Vegas on Labor Day weekend, and the list of events—live music and DJs in particular—is mind-boggling. You’ll find the Chainsmokers and Kygo at XS; Marshmello at KAOS; 2Chainz and Gucci Mane at Drai’s; Tiesto at Wet Republic; Travis Scott at Marquee; Rick Ross at LIGHT; Tyga at Jewel; Steve Aoki at Hakkasan; Martin Garrix at 1OAK; and DJ Snake at Encore Beach Club.

Stay at: The Wynn Las Vegas & Encore Resort

Encore Beach ClubPhoto Credit: Encore Beach Club

Sure, you want to party with the best of the best DJs and musicians in the world, but that doesn’t mean you have to sacrifice luxury to do so. The Wynn is a must for any true luxury enthusiast, because it meets every high-end need in one go. The rooms are opulent, the shopping is extraordinary—Off-White, Balmain and are just a few of the on-site boutiques—and the dining is exceptional (a few must-trys include Cipriani, the ode to Ol’ Blue Eyes, Sinatra, and Andrea’s, named for owner Steve Wynn‘s wife). In addition to music, comedian Ali Wong will be making you LOL and ROLF this Labor Day weekend. Maybe she’ll even bring Keanu.

3131 Las Vegas Blvd. South. Las Vegas, NV 89109

Martha’s Vineyard, MA

Martha's VineyardPhoto Credit: Brian Logan Photography/Shutterstock

There has, and always will be, a draw to Martha’s Vineyard in the summer. It’s bigger and more diverse than its nearby sister Nantucket, which means there’s more to do in the form of more shopping, a plethora of bars and restaurants and its current biggest draw—that our former President, Barack Obama, and his wife, Michelle, have shelled out $14.5 million for an oceanfront home in this Massachusetts island paradise.

Stay at: The Harbor View Hotel

Harbor View Hotel Photo Credit: Dan Cutrona

The Vineyard, despite being home to millionaires, billionaires and some of the world’s top actors and musicians (in addition to our former President, Carly Simon, Meg Ryan, Larry DavidJake Gyllenhaal and more all have homes here) but there is a surprising lack of luxury hotels. Cue the Harbor View Hotel, a beautiful piece of property by the Edgartown lighthouse, which just underwent a $15 million renovation, with more to come. Updates include refreshed rooms and two stellar restaurants—Bettini and Roxana—helmed by former Daniel chef Patrice Martineau. The hotel also has an exclusive new collaboration with Mercedes-Benz, where guests can take out any of its three house cars—an SUV, a sedan or a coupe—for three hours at a time to tool around the island while looking fabulous.

131 N Water St #8016, Edgartown, MA 02539