Escape this Labor Day Weekend to 8 Cool Luxury Destinations

Labor Day weekend is just around the corner. So, what are some last-minute luxury getaway destinations, and trips to take that don’t require a lot of prior planning? We’ve rounded up some of the best last-minute luxury getaways this Labor Day weekend.

Rooftop Pools, Lakes, and Dirty Dancing: 8 Last-Minute Getaway Trips for Labor Day You Need To Book Now

It’s hard to believe but summer is coming to a close and Labor Day is just around the corner. This means there is a fleeting opportunity to bid farewell to the season with one last exhilarating adventure: a last-minute Labor Day getaway. With the holiday weekend just around the corner, wanderlust-filled souls seeking a spontaneous escape find themselves presented with an enticing array of destinations and experiences. Whether it’s a tranquil retreat in nature, a vibrant urban escapade, or a sun-soaked beach retreat, these last-minute options offer the perfect chance to savor the waning days of summer and create enduring memories. So, pack your bags, seize the moment, and embark on an unforgettable journey with our handpicked selection of eleventh-hour Labor Day getaways.

The best last-minute getaway trips for Labor Day weekend

So where will everyone be going this Labor Day? According to data from Chase Travel this is where everyone wants to go if they are staying in the States: 

1. New York, New York
2. San Francisco, California
3. Los Angeles, California
4. Seattle, Washington
5. Chicago, Illinois
6. Boston, Massachusetts
7. Denver, Colorado
8. Washington, DC
9. Las Vegas, Nevada
10. San Diego, California

These are the favorite international destinations: 

1. London, United Kingdom
2. Rome, Italy
3. Tokyo, Japan
4. Paris, France
5. Athens, Greece
6. Cancun, Mexico
7. Calgary, Canada
8. Seoul, South Korea
9. Barcelona, Spain
10. Dublin, Ireland

So you can always follow the crowds or you can find a new place. Here are a few last-minute end-of-summer escape ideas if you want to blaze a new trail this weekend.

1. Burlington, Vermont

This small city is ideal for most travelers. Easily walkable and there are plenty of activities to keep you busy. Here are a few ideas on fun things to do:  

Lake Champlain

Experience the Champlain Islands including: 

• Alburgh is home to one of the longest beaches on Lake Champlain.
• Isle La Motte which is home to the world’s oldest coral reef Chazy Reef which is approximately 480 million years old.
• Grand Isle which is home to Breakaway Farm – a locally owned and operated horse farm with 160 acres of possible trail rides. While here, take advantage of one of their picnic rides, delicious wine tastings, and more. Travelers can also stay the night at Shore Acres, an incredibly cozy inn with spectacular views.

2. Miami, Florida

Or soak up those summer vibes in Miami, where they do it right. 

Arlo Wynwood

Arlo Wynwood has a special Labor Day package that includes room rates starting at $139 and includes late checkout, two complimentary cocktails at MaryGold’s, and daily breakfast.  It draws on the neighborhood’s bold and curated artistic nature while embracing an eclectic industrial aesthetic where organic meets modern. Guests are welcome to soak up the sun with sun at the rooftop, home to a heated pool and delicious poolside bites. 

Address: 2217 NW Miami Ct, Miami, FL 33127

The Gabriel Miami

Centrally located in downtown Miami, The Gabriel Miami offers 129 spacious rooms and suites with views of Biscayne Bay, ideally located near many of the city’s cultural institutions and top nightlife spots including E11even. Just a few blocks from the 24-hour club, which is hosting Deadmau5 this Labor Day weekend, The Gabriel Miami is the perfect spot to relax and unwind before or after partying all night. The hotel boasts two pools on the 14th-floor pool deck to keep you cool and refreshed: a serene resort-style rooftop pool with cabanas and an infinity lap pool with sublime views of the Intracoastal, Miami Beach, PortMiami and Biscayne Bay. 

Address: 1100 Biscayne Blvd., Miami, FL 33132

3. Chicago, IL

theWit 

Before it gets cold (which will be like five days later) head to Chicago, where they celebrate every second of summer. Located in the  Loop district, the property offers guests the unique opportunity to enjoy the serene beauty of the lake while being immersed in the vibrant urban atmosphere of Chicago’s mecca for shopping, arts, and theater. Visitors can embark on a leisurely walk or scenic drive along the iconic Chicago River to the lake, where they can rent boats, kayaks, or paddle boards, eat at one of the lakeside cafes, or sit in Rulland Grove park and enjoy the sunshine before heading back to the city to see all of Chicago’s must-see destinations, including the Bean and State Street. Having recently completed a multi-million dollar renovation, that boasts newly appointed guest rooms and suites and upgraded amenities and services, as well as internationally acclaimed ROOF, an indoor/outdoor dining venue with skyline views, handcrafted cocktails and cuisine, and the sleek and contemporary gastropub, State and Lake. Whether seeking relaxation amidst nature’s wonders or exploring the dynamic city life, theWit Hotel promises an unparalleled lakeside experience for travelers of all kinds.

4. McCall, Idaho

 Shore Lodge

Idaho is having a moment right now and the Shore Lodge is the ultimate lakefront destination allowing you to bask in all the  beauty of McCall, Idaho. Located on the expansive and pristine Payette Lake, you will be surrounded by rugged mountains as you spend the day away at this epic resort. It has 77 guest rooms and luxe resort amenities, including three acclaimed restaurants; The Cove at Shore Lodge, a full-service spa offering six treatment rooms and indoor/outdoor saltwater immersion pools; a year-round swimming pool and hot tub; and nearby local hot springs. And there are just so many activities! Guests can choose from paddle boarding, kayaking, and sailing on Payette Lake, whitewater rafting excursions, riding ATVs through Idaho’s backcountry, spectacular climbing spots, over 500 miles of hiking and biking trails, and horseback riding through the mountains. Celebrating its 75th Anniversary this year, guests can enjoy three celebratory packages and on-site programming including a sunset cruise that pays homage to the laid-back outdoor lifestyle of this hidden gem.

5. Williamsburg, New York

The Williamsburg Hotel (Soon to Be Arlo Williamsburg)

Soak up those last pool days of summer at the Williamsburg Hotel. When you aren’t at the rooftop pool, you will love your room with floor-to-ceiling windows and grabbing cocktails at the Lobby Bar, Mirror Bar, or Water Tower Bar.

 6. Charleston, South Carolina

The Spectator Hotel – Charleston, SC   

If you don’t mind a little end-of-summer heat then head down to The Spectator Hotel in Charleston. You will feel like you stepped back in time when you enter The Spectator Hotel—but with modern amenities of course—and you even can opt to have your butler! The butler will be your ultimate vacation planner and get you all those impossible-to-get reservations! He or she will also deliver handcrafted cocktails from The Bar, the Prohibition-era-themed cocktail lounge. 

7. Aurora, New York

The Inns of Aurora Resort & Spa – Aurora, New York 

Before that back-to-school rush, you need a little me time and that means getting pampered at a spa. The Inn of Aurora Resort & Spa, a boutique lakeside resort in the Finger Lakes is an excellent choice. The property is comprised of five exquisitely restored inns. When you aren’t spa-ing it up make new friends at the afternoon wine and cheese hour together in one of the Inns’ parlors.  

8. Shelter Island, New York

And in case you don’t make it out of town for Labor Day but can get away the next weekend, consider The Pridwin Hotel & Cottages in Shelter Island, If you are a Dirty Dancing fan—and honestly, who isn’t?— this is your time! The beautiful hotel will be hosting a “Dirty Dancing” themed weekend this September, from Friday, September 8 to Sunday, September 10.  The Pridwin is very reminiscent of the hotel where Dirty Dancing took place and they are leaning into it! No one puts Baby in a corner and no one puts you in a corner! 

The resort – which features 33 guestrooms and 16 luxurious camp-cabin-esque private cottages – is offering the ultimate Dirty Dancing Package. They will even play host to Ms. Eleanor Bergstein, writer, and co-producer of the film Dirty Dancing.

Weekend programming includes:

• A vinyl record player, playing the Dirty Dancing soundtrack, waiting for guests in their room as they arrive (and theirs to take home) 
• Dirty Dancing Happy Hour, featuring a themed “I Carried a Watermelon” cocktail and light bites 
• A poolside screening of Dirty Dancing, featuring movie snacks 
• An intimate conversation with Special Guest and storyteller: Ms. Eleanor Bergstein, the writer and co-producer of Dirty Dancing
• A “She’s Like The Wind” Sunset Cruise on The Pridwin’s private boat 
• A full American breakfast in the Terrace on Saturday morning 
• “Hungry Eyes” barbeque buffet dinner on the Pridwin’s Great Lawn 
• “I’ve Had the Time of My Life” farewell brunch on Sunday Morning
• Other surprises! 

This two-night exclusive package is available from September 8 to 10; rates start from $1,708 for two people. Additional room nights are available at prevailing rates.

The best last-minute getaway trips for Labor Day weekend

If you ask us, those are some of the best ways to make a last-minute getaway to a cool luxury destination this upcoming Labor Day weekend, including boutique properties in Brooklyn and Shelter Island. Book now, and have a great time, dear reader.