We scoured 80 Cyber Monday travel deals, and these 5 are legit worth booking

We’re usually meh with Cyber Monday travel deals. Honestly, many hotels offer a nominal percent off a package they have online.My favorite sale of all: “Stay 7 nights, get your last night 20 percent off!”.

This year, I found some serious “drop everything, this is too good to pass up” deals in my inbox.

Having seen hundreds of mediocre deals throughout the years, these five are actually incredible and should be taken advantage of. Cyber Monday is the Monday after Thanksgiving (11/27), so make sure you don’t go nuts over Black Friday!


1. VICEROY HOTEL GROUP- 40% off sale

This one is INSANE. On Cyber Monday, future Viceroy guests will have one full week (yes, the sale lasts 7 days!) to access 30 to 40% off Viceroy hotels and resorts, many with complimentary room upgrade. Deals will go live on www.viceroyhotelsandresorts.com.

THIS IS HUGE. Not even “family and friends” discount rates match this. The Cyber Monday deal includes their best properties, including Viceroy Riviera Maya, not only one of my personal favorite resorts, but among the top ten resorts in Mexico. I’ve never seen a deal like this at this specific property, and I’m surprised it wasn’t exempt.

NOTE: Viceroy Hotel Group rewards members and email subscribers will have early access to the sale (they can book as early as Black Friday) so it’s a good idea to sign up. Stays are available from November 20th 2017 – December 21st 2018. *Date range may vary per property. See below for some sample deals:

New York:






Viceroy Riviera Maya

Viceroy Riviera Maya

2. Mahekal Beach Resort,  Playa del Carmen- 50% off!

Mahekal Beach Resort made Conde Nast Traveler’s Reader Choice awards, and Travel & Leisure loves this hideaway. For Cyber Monday, the luxury resort is offering up to 50 percent savings with rates starting at $149/night, bookable Nov. 16* – Dec. 8, 2017 for travel Nov. 21, 2017 – Oct. 31, 2018. Guests booking four nights or more are rewarded with a $200 food and beverage credit per stay to be used at any of the five dining options on-property. Additionally, on Giving Tuesday, Nov. 28, Mahekal will donate 10% of all revenue generated that day to Cruz Roja Mexicana to aid in the country’s earthquake relief. For more information on Mahekal Beach Resort or to make a reservation, visit www.mahekalbeachresort.com or call toll-free 1(877) 235-4452.

Mahekal Beach Resort

Mahekal Beach Resort

3. Kimpton Taconic, Manchester, Vermont- Buy One Room, Get Next Night Free

Kimpton Hotels has been banging out some awesome newer properties that follow a hotel narrative with better design, rooms, service and food. I’ve been dying to check out Kimpton Taconic, a rustic, 87-room boutique hotel in the bucolic village of Manchester, VT. Kimpton Taconic is offering an exclusive Cyber Monday special for just 112 minutes and 7 seconds. On November 27th from 11:27 am until 1:19 pm, Cyber Monday shoppers can book a special Buy One Get One Free deal. When guests book a deluxe room at the special $201.50 rate (a nod to the hotel’s opening year, 2015)they will receive the second night free, for stays from November 17, 2017 through April 30, 2018Book online or by calling 866-518-8465. No booking code is necessary, the deal is subject to availability and blackout dates may apply. 

Kimpton Taconic

Kimpton Taconic

4. One Aldwych, London, England- Book 2 nights, get 3rd night free

This deal is actually GREAT. You don’t have to book an absurd number of nights to get one free. Also, hotels in London are notoriously expensive (luckily, the US dollar is strong, British Pound is weak, so there’s no better time to take advantage here). I’ve stayed at One Aldwych, and it is STUNNING. Starting on Black Friday and continuing through Cyber Monday, One Aldwych is offering a special “Three Nights for Two” deal. Located in the heart of London’s iconic Covent Garden, the luxury boutique hotel offers the best location for culture lovers with 25 theaters within a 10 minutes’ walk from the hotel, as well as superb dining and shopping options nearby. One Aldwych’s Cyber Monday offer is valid for stays from December 17, 2017 – April 2, 2018. Offer is valid for bookings made between November 24, 2017 at 12:01am GMT and November 27, 2017 at 11:59pm PST only. Blackout dates apply. Offer is subject to availability. Call +44 20 7300 1000 and quote “CYBER”.

One Aldwych

One Aldwych

5. The Peninsula New York and The Peninsula Chicago- 30% off stays

It’s rare The Peninsula Hotels offers discounts (they are almost always full, so they definitely don’t need to!). Seriously super rare, y’all. To get in the holiday spirit, The Peninsula hotels in Chicago (which I recently stayed at) and New York are offering unprecedented online specials from November 24 – 27, 2017, including great savings on room bookings as well as spa and dining. Enjoy a 30% savings on rooms and suites at The Peninsula New York and Peninsula ChicagoThe Peninsula Spas will offer up to 25% off select services in New York, Chicago and Beverly Hills with packages that include free upgrades, massages, facials, personal training and more at these award-winning spas. Additionally, each Peninsula Spa will be offering 10-20% off all gift card purchases. Culinary delights abound coast-to-coast as The Peninsula offers 10-20% off gift cards at their acclaimed restaurants, including Clement in New York, The Lobby and Shanghai Terrace in Chicago and The Belvedere, The Living Room, The Roof Garden and The Club Bar in Beverly Hills.

Peninsula Chicago

Peninsula Chicago

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Jimmy Im has traveled to 113 countries, stayed at over 600 hotels and clocked millions of air miles. He currently lives in New York City.

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