Where can you travel this fall and score a great deal? I’ve got the scoop!

Top Fall Travel Deals

Southern California

The Goodland Santa Barbara Hotel

SoCal is one of my favorite spots and the thought of sunning among palm trees pretty much sounds good anytime of year! I especially loved the fun Flashback Friday package offered by several Kimpton properties in Southern California that’s a throwback to the 90s and lets you channel your inner Ross and Rachel ;-).

Goodland Hotel California Santa Barbara

Credit The Goodland

At Hotel Palomar San Diego, Hotel Solamar (San Diego) and The Goodland in Santa Barbara (which I have visited and makes my list of favorite hotels; it’s so cool!), you not only get 15% off the best rate but an assorted pack of 90’s candy upon arrival and an exclusive, specially-curated Spotify playlist of 90’s jams—think *NSYNC, Red Hot Chili Peppers, Guns N’ Roses and Shaggy.

Plus, at The Goodland, you can enjoy a 90’s themed movie poolside on Friday, like “Clueless,” “10 Things I Hate About You” and “She’s All That.” Rates start at $203 and must include a Friday night.


Hotel Monaco Chicago

Credit Hotel Monaco Chicago

Is there a better time of year to see a Cubs game than the fall? Why not head up to Chi-town (especially close for us Hoosiers) to see the team at their best when the weather is cool? We went to a Cubs game (my first!) last weekend and the weather could not have been better.

Kimpton’s Hotel Monaco is centrally located downtown just below the Chicago River at the top of The Loop and just a block from Michigan Avenue. You can enjoy dinner at one of the many restaurants in the area (including plenty of deep dish options like Gino’s East and Lou Malnati’s) and take the train up to Wrigley Field. Easy peasy. Their window seats in every room are not to be missed and one of my favorite hotel features ever!

They have several deals this fall. Residents of the Midwest (including Illinois, Indiana, Ohio, Kentucky, Missouri, Iowa, Wisconsin, Michigan or Minnesota) can score up to 20% off and get a late 1 p.m. checkout, perfect if you’re catching a 1:30 Cubs game. Or extend your weekend with your third night free for stays beginning on a Friday. I also love their We Be Cubbin’ package with 10% off, 3-day train passes for 2, 2 craft beer flights at their on-site restaurant and a Wrigley Field Stadium Tour for 2.

Hilton Head Island, South Carolina

Palmetto Dunes Hilton Head

Credit Palmetto Dunes Oceanfront Resort

Also driveable, though it will take you about a day :), is Hilton Head Island in South Carolina. Of course, you could also opt to hop a flight to Savannah, the closest airport, which is about 45 minutes from the island. Palmetto Dunes Oceanfront Resort offers a variety of affordable vacation villas and homes with kitchens, washer/dryers and separate bedrooms so you can enjoy a more homelike stay at the beach. There’s something for everyone at the resort, including 3 miles of beautiful beach to golf, tennis, pickleball (an up and coming sport), biking, fishing, kayaking and more.

Their vacation rentals start as low as $139 per night for a one-bedroom this fall, less than you will find at many hotels, but with so many more comfortable amenities. You can choose from vacation packages like the three-night Sun ‘n Fun Island Escape with golf, bike rentals, tennis time, kayak rentals and even a spa treatment starting at $185 per person per night.


Estes Park fall

Credit Visit Estes Park, See elk in Estes Park in October!

If you’re a regular reader of Go to Travel Gal, you know one of my favorite places on earth in Colorado. September may be one of the best months to visit with the aspens changing to shades of gold. October is the off season for most resorts and towns, so while some restaurants and stores may be closed, it’s also a nice quiet time of year and extremely affordable. Keep in mind though that in October, you could run into snow (I have!).

At Keystone Resort, one of the closest resorts west of Denver, you can save up to 40% off stays of two nights or more with rates on condos starting at just $119/night. Be sure to take a gondola ride open on weekends for awesome aspen viewing. In Vail, visitors can often find two for one or special prix fixe menus at many of the local restaurants and there are spa deals galore! Rates at many Vail hotels start at just $140/night in the fall.

Book a stay at the Viceroy Snowmass in the back hills of Aspens and another of my favorite hotels. There are fireplaces in every room that you can light with the touch of a remote — perfect for snuggling up on a crisp fall day after a long hike in the cool weather. They offer a special package for those who want to try the Aspen to Crested Butte 10-mile one-way hike, providing transportation to and from (via helicopter if you want!) the trailhead and a gourmet picnic lunch.

Finally, in Estes Park, just outside Rocky Mountain National Park, they refer to October as elk-tober because the elk gather in large numbers from mid-September to mid-October. Visit the park during dawn or dusk for the best chance to see them and keep an ear out for the elk “bugle.”


Caribbean fall deals

Credit Maya Beach Hotel

Fall is a great time to visit the Caribbean, because prices drop significantly. Why? A large part is because it’s hurricane season, so you are taking a risk if you book a trip to this tropical destination.

Purchasing trip insurance from a company like InsureMyTrip.com is a good idea and keep in mind many hotels offer a “hurricane guarantee.” This usually means they will reschedule you or even offer a refund in the event of a hurricane headed to the area. Be sure to keep checking weather before you head out and when you arrive and it never hurts to have an emergency kit handy just in case. Here are more tips on Traveling During Hurricane Season.

The area of Nassau with average fall highs in the mid-80s has some great fall deals with one of the most popular resorts, Atlantis, offering an all-inclusive package with meals, activities and accommodations for $299/night for adults and $99/night for kids. The British Colonial Hilton, on the only private beach in downtown Nassau, has rates starting at $199/night with a $50 daily resort credit.

Six Club Med properties in Mexico, the Bahamas and Turks & Caicos has room rates starting at $119, usually $249, for stays three nights or longer. Plus, they offer half off stays for kids 15 and younger and free stays for kids 4 and younger. Book by September 27 for stays October through mid-February.

Lastly, the Maya Beach boutique hotel in Belize has rates starting at just $90/night through November (though note the hotel is closed through September 30). All rooms have views of the Caribbean Sea, private porch or balcony and personal hammock.

10 Things You Can Do to Start Flying Free TODAY!

Airplane palm trees

Enter your email to get a free PDF that shows you 10 easy things you can do to begin your journey toward flying free RIGHT NOW! You'll also be added to Go to Travel Gal's weekly email newsletter list.

We won't send you spam. Unsubscribe at any time. Powered by ConvertKit