The Best Time to Book Holiday Travel Deals, per Experts

You might still be segueing from flip-flops and iced coffee to Uggs and a steaming PSL, but it’s time to get your head around holiday travel — because right now is when experts say you can score the best travel deals and get the widest availability. 

“For holidays, the best times to book are as early as possible,” says Dynamite Travel owner Dr. Terika Haynes, noting the early booking trend ramped up after the pandemic. “Travelers are booking up to one year — and sometimes more than one year — in advance for festive/holiday season travel. And since pricing is typically based on availability, booking earlier will yield better rates.”

Doni Belau, founder of the woman-only travel company Girls’ Guide to the World, underscores the point: “If you want to travel during the holidays, you can’t book early enough.” Why? “It’s simple supply-and-demand economics,” she continues. “There’s tremendous demand during the holiday season and airlines and hotels can’t meaningfully increase supply.” Belau also stresses that early booking is particularly important if your travel dates are inflexible. 

In order to make sure you lock in the best possible price for your holiday getaways, Haynes recommends setting price change alerts to monitor price drops and booking travel protection that includes price protection. Her second tip? Don’t wait until Black Friday to book as “sometimes pricing is increased before discounting to create the illusion of a better deal than it is.” Additionally, she points out, “Sometimes, Black Friday deals will have blackout dates that are not included in the promotion and usually they are the popular dates that most will want to travel.”

Best Travel Deals to Book Now:

In short, the key takeaway here is: if you see a great deal now, book it. Taking Haynes and Belau’s advice in stride, we scoured the web for the 32 best holiday travel deals that you can score today up to 75 percent off — from flights and hotel stays to vacation bundles and cruise packages.

Best Hotel and Resort Deals 

Hawks Cay Resort, Florida Keys: The largest resort in the Florida Keys, Hawks Cay Resort is offering a Thanksgiving deal to save up to 35 percent off on a stay of four nights or more (so it’s ideal for Thanksgiving weekend fun). Book now through October 31 for stays from November 27 through December 1.

Sunset at the Palms, Jamaica: This all-inclusive adults-only resort in Negril has 85 treehouse-style rooms for a cool jungle-like experience a short walk from one of the most coveted beaches on the island. The resort is offering an Extend Your Summer sale, available now through October 31, with select travel dates from December 14 through April 11, 2025. This represents savings of up to 69 percent (up to $1,000 off) using the code “SUM24” on a seven-night getaway in a deluxe treetop room. Rates are as low as $173 per person, per night.

Faena Miami Beach: Book five nights at Faena Miami Beach and get the fifth night free. This winter travel package is valid from November 4 through April 30 (with some restrictions and blackout dates). The five-star beachfront property is situated on an iconic stretch of South Beach, providing the perfect winter getaway. 

Conrad Punta de Mita, Mexico: Spend the holidays at Conrad Punta de Mita with the property’s Seaside Greetings package, which offers 20 percent off its luxe accommodations and up to $500 resort credit this holiday season. Use the code “FESTIV” when booking online.

Jamaica Inn, Stay four nights at the longtime family-run Jamaica Inn in Ocho Rios from December 20 through December 27 and receive Christmas night free. The offer is available in all suites and cottages for single or double occupancy on a room-only basis.

Hilton Los Cabos, Mexico: Hilton Los Cabos, located along one of the area’s rare cove-protected beaches, is offering a two-week-long festive season schedule with tree-lighting ceremonies, helicopter Santa visits, yuletide-themed crafts, and more, from December 18 through New Year’s Day. The Joy of Festive deal offers 10 percent off with a $350 resort credit for any booking for three or more nights. Check out the Spread Holiday Cheer package, which offers 50 percent off when you book a second room.

King Kamehameha Kona Beach Resort, Kailua-Kona, Hawaii: The Golden Sunsets & Savings Deal offers 30 percent off at King Kamehameha Kona Beach Resort. Use promo code “E4000” and book by October 31 for stays through May 31, 2025. The culturally rich resort encompasses the land where King Kamehameha ruled, sitting on 13 idyllic beachfront acres adjacent to the Kailua Pier. 

Mondrian, Los Angeles: Book now to get 20 percent off suites at the iconic Mondrian on the Sunset Strip. You’ll also get a $25 daily F&B credit, plus early check-in and late checkout.

Aspen Meadows Resort, Aspen: The Aspen Meadows Resort goes big for the holidays with a reindeer village, carolers, sleigh rides, gingerbread house, and cookie decorating, plus special holiday menus and happy hours. Book by November 15 and stay at least three nights to score 25 percent off accommodations as well as a $75 breakfast credit per night and ski shuttle service included. 

SLS Playa Mujeres, Mexico: SLS Playa Mujeres, the first all-inclusive from SLS, is set to open on November 3. For the holidays, receive 50 percent off stays from November 15 through February 14, 2025, with no blackout dates, through the “Disloyalty Program.”  

Atlantis Paradise Island, Bahamas: Bundle flights with stays at any of Atlantis Paradise Island’s properties for up to 35 percent savings through 2025. With stays at The Royal, The Cove, The Reef, or The Coral, enjoy additional resort credits up to $400. Book between now and November 22.

Marriott Cancun, Mexico: The Marriott Cancun, An All-Inclusive Resort, the first all-inclusive property fully conceptualized by the Marriott brand, just opened in September. Book through October 31 to get 30 percent off stays of seven nights or more, and 25 percent off stays of four or more nights using promo code “HOL.” Travel November 22 through January 20, 2025.

Sandestin Golf and Beach Resort, Florida: Gather with family at the Sandestin Golf and Beach Resort this Thanksgiving and save up to 25 percent off two nights or more with the resort’s Give Thanks & Celebrate offer. The 2,400-acre resort sprawls over 70 charming neighborhoods with over 1,000 vacation rentals just right for Thanksgiving getaways. Book this offer online using code “TURKEY.” It’s valid only for two- through seven-night stays arriving between November 23 and 28, and departing by December 1.

The Marker Key West Harbor Resort, Florida: The Marker Key West Harbor Resort, located on the Historic Key West Harbor, features lush tropical grounds, three saltwater pools, an open-air restaurant and bar, and 96 spacious guest rooms with private balconies. With the Marker’s exclusive holiday travel deal, book between November 21 and December 4, and receive 35 percent off all room types, plus a $50 resort credit.

AVA Resort Cancun, Mexico: Opened this summer, AVA Resort Cancun is offering a holiday pre-sale offer offering up to 27 percent off any of the room categories, free roundtrip transportation, and early check-in and check-out. Book by October 31 and travel from December 18 through January 4, 2025. The resort has 1,600 rooms, all with ocean views.

Best Hotel Deals 

Hyatt: From the snowy peaks of Vail to the beaches of Maui, save up to 20 percent at select Hyatt resorts (World of Hyatt members save even more). More than 70 properties are participating across the U.S., Mexico, Latin America, and the Caribbean (including Alila Napa Valley, Grand Hyatt Vail, Hyatt Ziva Cancun, and the Hyatt Regency Maui Resort & Spa). Members must register by October 2, 2024, and stay between October 1 and April 30, 2025.

NH Collection: With the City Dreamers special offer, lock in up to 30 percent off at select NH Collection hotels such as the NH Collection Copenhagen, NH Collection Amsterdam Barbizon Palace, NH Collection Amsterdam Flower Market, NH Collection Vien Zentrum (Vienna), and the NH Collection Brussels Grand Sablon. 

Small Luxury Hotels of the World: With the Stay Longer, One Night on SLH offer, get a free night reflected in the total price on qualifying bookings of three nights or more when you book at one of the luxury participating SLH hotels. 

Marriott Luxury Group: Book your stay by October 31 and get discounts at participating Marriott Luxury hotels and resorts across the Caribbean and Latin America, including the soon-to-open Almare, a Luxury Collection, The Ritz-Carlton Aruba, The Riviera Maya Edition at Kanai, and Dorado Beach, a Ritz-Carlton Reserve. Stay four nights or more and get 25 percent off your booking, or extend your trip to seven nights or more and unlock a larger 30 percent discount. This offer is valid for travel dates between November 22 and January 20, 2025. Find a full list of participating properties here.

Pebble Beach Resort: The Winter Differently package is available at two Pebble Beach Resorts properties — The Lodge at Pebble Beach and The Inn at Spanish Bay — and is available to book now for a stay between December 15 through the end of January 2025. Stay at The Lodge at Pebble Beach for 21 percent off ($925 nightly) or The Inn at Spanish Bay and get 23 percent off ($795 nightly). Returning guests receive a one-level room upgrade with a qualifying stay. And you’ll get a free round of golf when booking a third night at Spanish Bay ($350 savings).

Best Flight Deals

Priceline: With Priceline, you can save up to $625 on your hotel and flight when you book a vacation bundle. Or, you can opt for one of the site’s package deals, which include roundtrip flights and hotel stays to Chicago, Hawaii, and New York City starting at $242 per person. 

JetBlue: JetBlue has one-way flights to tropical destinations like West Palm Beach and Fort Lauderdale in Florida, Los Cabos, Mexico, and Montego Bay, Jamaica starting at $104 for a limited time. Explore more deals for more cities here. 

Southwest: For a limited time, Southwest is offering savings of up to $250 on select vacation packages; bundle your flight and hotel through October 14 to take advantage of this deal. Note: restrictions, exclusions, and blackout dates may apply; one-day advanced purchase is required and the promo will be applied at checkout. 

United Airlines: Scroll through United’s special flight offers to score discounted flights from Chicago, New York City, Denver, Los Angeles, and other major cities. Already thinking of winter break plans? A roundtrip flight from Chicago O’Hare International Airport to Miami International Airport on December 9 to December 16 starts at $119; a roundtrip flight from Houston’s George Bush Intercontinental Airport to Honolulu’s Daniel K. Inouye International Airport on December 14 to December 24 starts at $923; and a roundtrip flight from Los Angeles International Airport to London Heathrow Airport on November 24 to December 10 starts at $607.

Delta: Use Delta’s Current Flight Deals selection to save on your roundtrip flight home for the holidays; prices start as little as $134 depending on your destination. Blackout dates may apply, so make sure you pay close attention to the timeframe that applies for each deal.  

American Airlines: Did you know that American Airlines has special vacation package deals? For example, you can save up to $150 on a trip to the Caribbean. Other destinations include Nickelodeon Punta Cana and MGM Resorts Las Vegas; check out the airline’s travel deals section for the full offer details.   

Frontier: Frontier fliers have plenty of flight deals at their fingertips. Prices start as little as $80 for one-way flights in December from select destinations. Word to the wise, pay close attention to the dates when booking.

Alaska Airlines: Get the lowest airfare rates for your holiday travels with Alaska Airlines’ limited-time offerings on one-way flights to and from select destinations. Book through the deals portal to save big. 

Best Cruise Deals

Celebrity Cruises: Every week, Celebrity Cruises drops a fresh batch of “Exciting Deals” so travelers can enjoy last-minute rates on voyages to top destinations like the Caribbean, the Bahamas, Europe, and more. But during Celebrity Cruises’ Fall Sale, you can save up to 75 percent on your second guest’s cruise fare to the Caribbean, Europe, Alaska, and other top vacation spots. Plus, additional guests in your stateroom sail free on select Bahamas and Caribbean sailings. And, for a limited time, you can book a veranda stateroom at ocean-view rates (with a bonus of up to 75 percent on your second guest’s cruise fare). 

Heritage Line: Heritage Line, the boutique cruise line that sails through Southeast Asia, is offering a $750 discount per person on seven- to nine-night journeys aboard the newly redesigned and relaunched vessel Anouvong on the Upper Mekong from November 23 to February 20, 2025. This discount is also available on seven-night journeys along the Lower Mekong River, operated on Heritage Line’s luxury boutique ships, The Jahan or Jayavarman. Enhance your journey with optional cycling and culinary tours, which are available for advanced booking (cycling) or included at no extra cost (culinary). The booking window is now through the end of October.

MSC Cruises: MSC Cruises is offering cruises as little as $249 cruise prices and kids sail free on sailings in November and December (and into 2025) throughout the Caribbean and the Mediterranean. Sailings can be found here.

AdventureSmith Explorations: Swap snow boots for flip-flops and go searching for turtles, whales, dolphins, sea lions, and other marine life in Baja, Hawaii, or Galapagos with AdventureSmith cruise deals. Book the In Steinbeck’s Wake sailing in Baja from December 18 through December 28, and get 20 percent off plus $500 off per child and the second child free, with a waived solo supplement. Or book the Hawaiian Seascapes sailing (December 21 through December 28 or December 28 through January 4, 2025) and the Darwin’s Galapagos Discoveries (December 19 through December 26) and score 10 percent off on each.

Love a great deal? Sign up for our T+L Recommends newsletter and we’ll send you our favorite travel products each week.