Tips for Scoring the Best Fall Travel Deals

Castello di Vicarello - view of pool and Tuscan in background.

Six months ago when the travel industry was beginning to see the light at the end of the tunnel, absurdly low prices on flights and hotels were still easy to find and flexible last minute cancellation policies were baked into nearly every booking. Now, with air traffic almost back to pre-pandemic levels, the hot deals aren’t quite as scorching (or nearly as obligatory). According to a recent survey from the travel booking app Hopper, lodging prices in the U.S. are up 42% from earlier this year, and are expected to rise even more by the winter holidays. Which doesn’t mean the deals don’t exist—it just means you'll need to be a bit more clever when booking travel for the next few months. Here, we round up the best insider tips for scoring travel deals this fall.

Time it right

Don't wait too long to commit, especially when you're booking a vacation rental. According to the property management vacation rental platform Guesty, November and December reservation volume in the U.S. is up 157% compared to the same period in 2020, and already 80% higher than in 2019. Their advice: book your holiday Airbnb soon, as in now. Book later, and you’ll “risk having significantly less inventory to choose from, at higher prices.” Timing is also essential when you're looking to score great deals on flights. Typically, the cheapest days to fly are midweek, departing on a Tuesday or Wednesday and returning on a Tuesday or Wednesday, according to Hopper. And the day you return matters somewhat more than when you depart, with domestic flight midweek departures saving you around $20 round-trip and midweek returns saving you around $30 round-trip. Hopper also advises booking at least 30 days in advance for a hotel in a resort area—and to do exactly the opposite for city center hotels (book these less than two weeks from arrival to potentially score last-minute deals when inventory opens up, and keep your eyes peeled for midweek specials). Finally, if you’re the spontaneous type, apps like Hotel Tonight and Hopper’s Stay the Night offer great deals on last-minute bookings (to wit: on the Hopper app, you can save 25% on off-peak prices when you book within 48 hours of check-in).

Consider going all-in

Peak season travelers might want to consider bundling their flight and hotel accommodations via an all-inclusive travel package. A packaged holiday is almost always cheaper than going à-la-carte, requires little planning on your end, and saves you time since the operator does all the heavy lifting of arranging hotels, flights, car transfers, and excursion bookings. Plus you’ll be looked after if something goes wrong (e.g. cancelled flights or accidental double bookings at resorts). You'll find some excellent travel packages on JetBlue Vacations, the first domestic airline in the United States to offer customers the ability to book their flight, cruise and hotel all in one place. JetBlue Vacations recently offered a three-night trip to Palm Springs for two in October with prices starting at $949 per person, including round-trip air fares from New York and a room at the JW Marriott Desert Springs Resort and Spa. Costco Travel has some unexpectedly luxurious resort travel deals too—think the Four Seasons in Bora Bora or a “Best of Italy” trip to Rome, Florence, Venice. 

In case a car rental is not included in your travel package, you'll find the lowest prices on metasearch engine sites like Momondo or Kayak. You’ll never actually book your trip on Momondo—instead, you can use the site to search for the best prices, then you’ll get transferred to that rental agency or online travel agency to book. Momondo also offers "Surprise Agency" reservations: opaque bookings with even better prices, but you won’t know the rental agency until after you complete your transaction. Finally, consider "cancel for any reason" travel insurance. If you have to cancel your booking because of a quarantine or border closure, you could be out of pocket for most of what you've already paid. With “cancel for any reason” policies, you can still recoup prepaid expenses.

Explore slow-to-recover destinations 

While it pays to do your research relative to Covid safety and other factors before trotting across the globe, there are real deals to be found in destinations that have been slow to recover from the pandemic. Joali Maldives is offering 25% off its best flexible rate on a bed-and-breakfast basis for two people with a minimum four-night stay, valid until December 20. Located on Muravandhoo island on the Raa Atoll in the northern Maldives, each of this sustainable resort’s 73 villas and rooms is an artistic wonder offering a calming aesthetic featuring high ceilings, a sun deck with plush loungers, a private swimming pool and direct access to the beach. In the Dutch Caribbean, Bamboo Bonaire resort is taking $45 off its nightly rates for cottages, which start at $179, on stays of three nights or more until December 18. If you're planning a holiday around wine tasting and prefer not to cross the Atlantic, check out Willamette Valley in Oregon—a solid, affordable alternative to the pricier Napa. For an affordable beach getaway, consider Destin in the Florida Panhandle or the charming town of St. Augustine on the eastern side, rather than a more costly Miami visit.

Book business travel hotels 

Booking hotels that cater to business travel is a smart way to save, given that this demographic hasn’t rebounded as quickly as resorts and vacation hotels. Rubbing elbows with the National Portrait Gallery, the Kimpton Hotel Monaco in Washington, D.C. is offering between 5% and 20% off Kimpton’s best flexible rate this fall when you book at least seven days in advance. The exclusive Fitler Club in Center City Philadelphia is offering discounted rooms that include full club benefits for autumn stays. Housed in a historic building in the heart of Union Square, Palihotel San Francisco is currently offering an 18% discount on rates when you stay three nights or more.

Let the deals come to you

Obsessed with a certain hotel or resort? Get on their mailing list, explore the offers page on their website, and follow them on Instagram (where they sometimes share flash deals). Another overlooked yet effective tip: pick up the phone and call. Some hotels will offer unpublished discounted rates to those who book directly (or return guests). Nestled in southern Tuscany's Maremma hills, Castello di Vicarello is a boutique luxury hotel with nightly rates starting at $430 in the off-season. On the offers section of their website, you'll only find a form inviting you to email them with your dates of interest plus any special requests. We reached out and scored a 10% discount plus a room upgrade on a two night stay in October. And don't forget tried-and-true travel clubs like the good old Triple A. Members receive exclusive discounts through programs like AAA Hot Deals. Finally, scan your credit card membership rewards portal to see if they are offering special deals on points transfers to hotel groups like Marriott Bonvoy and Hyatt Hotels.

Call in the experts

For those planning a high-end vacation, consider reaching out to a professional travel adviser. You will have to pay a fee (often baked into the package price), but it could be well worth it as advisers have a birds-eye view of the best luxury deals in the market, VIP access to once-in-a-lifetime experiences (e.g. skip the lines at Angkor Wat or see the Sistine Chapel after hours), and the ability to throw in a bunch of freebies like room upgrades and complimentary breakfast (not to mention spa treatments). Look for those affiliated with a consortium, like Ensemble, Travel Leaders or Virtuoso, which use their collective buying power to get deals. After all, who wouldn’t mind their third night free in the Maldives?

Reading next

Sea view from Porto Pino in Sardinia
Camp Sarika Aman Hotels

Leave a comment

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.