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Note: All travel is subject to frequently-changing governmental restrictions—please check federal, state, and local advisories before scheduling trips. 

OK, we’ll rip the bandaid off quickly and just say it—summer is almost over. If it seems to you like it’s gone by in the blink of an eye, you’re not alone. But summer coming to an end doesn’t mean the fun has to. Before winter rears its chilly, dreary head, we get to soak in all things autumn. For some, that means hikes surrounded by brilliantly colored fall leaves, for others, booking trips to places that are finally less crowded. For you, it can mean jetting off to one of these 8 places that truly shine in September.

RELATED: Every top new attraction in each of your favorite U.S. cities

Palm Springs, CA

Shot in Palm Springs California on Fuji Superia film stock, natural film grain, no added grain.

Hands down one of our favorite California destinations, this desert locale is blazing hot during the summer months. Come September, the temps are far more enjoyable and crowds from music festivals have long gone home. Hikes, golf, and lazy pool days await, as do plenty of great restaurants along the strip downtown (don’t sleep on Cheeky’s!). Holiday House Palm Springs is the perfect place to stay. It’s pet friendly, breakfast is included, the pool is lovely and the bright cheery rooms set the tone for a wonderful weekend retreat.

The Catskills, NY

Fall Color Reflected On Lake.

There are a few places around the country that truly light up during fall and Upstate New York is one of them. The leaf-changing season here is brilliant, featuring colors you’ve probably never even seen before, so go ahead and explore the forests and all their sights to take in. Outdoor activities like hikes to Kaasterskill Falls and fly fishing on Esopus Creek are epic in the fall. The Graham & Co in Phoenicia is a newly renovated motel you’re sure to love and it’s a quick drive to the Phoenicia Diner, where you just gotta stop in for breakfast.

Telluride, CO

A gondola at Telluride Mountain in Colorado during fall colors

September in Colorado is really special and if there’s fall magic to be found, it’s in Telluride. Summer heat has subsided, fields are still littered with wildflowers, and theres’ a slight chill in the evening air that hints of things to come, but the days are still long enough to enjoy all there is to do. Spend the night at Dunton Hot Springs, a stunning boutique property with amazing food, hot springs to soak in, plenty of hiking trails, and lots of lovely spaces to relax and unwind.

ALSO: Join Orbitz Rewards and earn perks and travel dollars good toward your next hotel stay!


rainbow over west maui mountains on a blue sky day

Maui is another destination that, come winter, becomes jam packed with tourists escaping frigid temps and the hotels capitalize on that with super-high rates. Visiting during shoulder season is an excellent idea and whether it’s a romantic getaway or a group trip, we love the Kaanapali Alii. Its condo style accommodations allow you to spread out and cook meals at home if you like, the pool is beautiful and the property is set right on the beach. Plus, you can stroll down to Whaler’s Village or drive a quick 5 minutes or so to Lahaina. Note: Be sure to check local Covid guidelines before booking.

Santa Barbara

This is a photo of the Santa Barbara pier in California. There is a lot of space for copy or cropping.

One of the loveliest cities in America, in our opinion, there’s no wonder people flock there year round. Temperatures stay pretty mild all the time but September is especially lovely. Hotel Californian, right in the Funk Zone, is a great place to stay. You’ll be walking distance to tasting rooms and close to many good restaurants, like the Lucky Penny.

Kiawah Island, SC

Sunset from the deck of the Ryder Cup bar at Kiawah Island, South Carolina overlooking the 18th green

Golfers know about Kiawah Island, a barrier island off the coast of South Carolina, but people who enjoy beautiful beaches and good food should add it to their lists, as well. Stay at Kiawah Island Golf Resort and hit the links, then spend the afternoon at the beach. By late September, the brutal southern summer heat and humidity will have dissipated, but it’ll still be warm enough to enjoy the outdoors.


Bermuda also referred to as the Bermudas or the Somers Isles, is a British overseas territory in the North Atlantic Ocean, located off the east coast of the United States. Its capital city is Hamilton.

People are always amazed at how close Bermuda is to the U.S.—just 850 miles off the coast of North Carolina. That means from New York City, it’s faster to fly to Bermuda than Atlanta! For couples or families with older kids (no one under 13 allowed), we love Cambridge Beaches Resort & Spa. A sprawling property and one of the oldest resorts on the island, the quaint guest houses are painted in sea-shell pink, reminiscent of Bermuda’s famed pink sand beaches. The color of the water is unlike anything you’ve ever seen before. The shades of blues, greens, and turquoise seem to glow ultra-violet when the mid-day sun hits the water just right.

Big Sky, MT

horses in front of mountains

Yes, people flock here in the winter to hit the slopes, but September is secretly a wonderful time to visit. The crowds have yet to arrive, it’s not freezing (yet!), and the leaf peeping is top notch! Stay at the The Wilson Hotel for the perfect location, a great pool scene, and plenty to do outside right at your fingertips. Think fly fishing, hiking, zip lining, and golfing!


Tagged: California, Caribbean, Colorado, Hawaii, Top 10 Lists

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Compass + Twine
Sarah Driggs and Lindsay Ridenour are the story-tellers behind the NYC-based luxury travel blog, Compass + Twine. Follow along on Instagram @compassandtwine as they unearth some of the best hotels and travel experiences around the globe. From scenic landscapes to local cafés, they reveal the true character of a destination, always highlighting the best place to stay on .

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