12 best Cyber Monday travel deals, handpicked by Travelbinger (Updated)

Mondays are better than Fridays… in holiday sales.

Cyber Monday hit $7.9 billion in sales last year, compared to Black Friday’s $6.2 billion. They were record setting sales for both Black Friday and Cyber Monday, proving that more people are shopping online. Fortunately, this includes travel.

Flight and hotel deals are aplenty on Cyber Monday, and travelers can find plenty of bargains from sites like Delta.com or Marriott.com, individual hotel websites (like Refinery Hotel New York) and top travel company Viator, known for offering great deals on packages, tourist attractions and excursions. 

Some travel companies *really* get in the holiday spirit. We’ve seen some of the best travel deals go on sale on Cyber Monday, and trust us… they don’t last.

Travelbinger scoured nearly 100 travel deals for our readers, and these ridiculous sales are too good to pass up.

12 Best Cyber Monday Travel Deals 

1. Peninsula Hotels — 30% off rooms

Peninsula Hotels rarely offers discounts since the luxury brand keeps a high standard (and high occupancy). For Cyber Monday, Peninsula is offering up to 30 percent off three of their most popular hotels: The Peninsula New York – Up to 30% off (available for stays from January 1 – March 31, 2020); The Peninsula Beverly Hills – Up to 25% off suites (available for stays from December 2019 – April 2020); and The Peninsula Chicago – Up to 30% off (available for stays from December 15, 2019 – April 30, 2020). 

Visit this link to book.

The Peninsula Beverly Hills

2. Casa Kimberly in Puerto Vallarta, Mexico- 50% off room rates

I was the first guest to stay at Casa Kimberly, Elizabeth Taylor’s private home in Puerto Vallarta, Mexico. 

A luxury boutique hotel, Casa Kimberly is offering 50% off all accommodations. The hotel is quite special, completely renovated while embracing the original structure and featuring nine suites, a pool, boutique spa and an open air, upscale Mexican restaurant, The Iguana. It’s elegant, and just steps from Old Town Puerto Vallarta. 

At 12:01 a.m. November 29 to December 2 11:59p.m., travelers can book Casa Kimberly for stay dates of December 1, 2019 to May 31, 2020. Use the code CYBERCK to receive the discounted rates.

Casa Kimberly in Puerto Vallarta.

3. Amtrak — 30% off nationwide travel

Amtrak, the national rail operator, operates more than 300 trains daily, connecting more than 500 destinations in 46 states, the District of Columbia and three Canadian Provinces, and many routes offer stellar views.

Amtak’s highly-anticipated “Track Friday Sale” returns this year. Details are kept under wraps until the deal goes live on Amtrak.com on November 29, but last year’s offer included 30% off nationwide train travel.

Visit https://www.amtrak.com/home.html when the deal goes live November 29, 2019

Southwest Chief near Fishers Peak, Colorado. Amtrak.

4. CheapCaribbean – Up to 70% off vacations

CheapCaribbean, an online travel agency specializing in beach vacations to the Caribbean, Mexico and Central America, with 600+ properties located right on the water, is offering up to 70% off all-inclusive 2019/2020 bookings from November 7-December 2, 2019.

Through this sale, all-inclusive vacation prices start as low as $349 and are the lowest prices of the season for last-minute and spring break travel.

Sample deals include:

Occidental Tucancun, Cancun – 4 nights from $499: Just a few miles from the lively city of Cancun, the Occidental Tucancun boasts 336 fully-equipped rooms and suites as well as impressive views of the Nichupte lagoon. The property has three pools for adults and children, one with a hammock area inside the pool.

Tamarijn Aruba All Inclusive, (kids ages 12 and under stay & eat free) – 3 nights from $849: Tamarijn Aruba redefines family-friendly with an array of activities like windsurfing, beach volleyball, a 30’ rock climbing wall, kayaks, snorkeling and more.

Warwick Paradise Island (adults only), Bahamas – 3 nights from $629: This age 16+ property is the perfect refuge from everyday life. The resort has 244 rooms boasting a view of either Nassau Harbour or Paradise Island, a spacious pool with a whirlpool, five separate dining spots and Cabbage Beach is a short stroll away.

Yelapa Beach in Mexico.

5. Refinery Hotel, New York City: 60% Off

I recently had a staycation at the Refinery Hotel in New York City. It’s one of my favorite hotels in the city! And 60 percent rates off hotel rooms is almost unheard of in NYC. 

Refinery Hotel features fashion-forward loft-like guestrooms with custom furniture, original artwork, 12-foot high ceilings and Frette linens. The property is home to Parker & Quinn (an American bistro), Winnie’s Jazz Bar (a prohibition-style bar), and Refinery Rooftop (a stunning indoor/outdoor rooftop lounge with views of the Empire State Building), making it the perfect stay for a classic New York City visit.

In honor of the hotel’s 6th anniversary, Refinery Hotel is offering a 60-minute flash sale with 60% off their Atelier Suites from 6-7pm EST on both Black Friday and Cyber Monday.

Visit this link to book.

Suite at Refinery Hotel. Photo: Jimmy Im

6. Hotwire – 11% off hotel rates

While this isn’t a groundbreaking deal, this discount with Hotwire.com comes in handy for those who already plan to book here. 

Book a hotel for any date with Hotwire’s sitewide on December 2 and take an extra 11% off $100 Hot Rate Hotels with promo code: HWHOTDEALS

Jumeirah VIttaveli, Maldives.

7. Generator – up to 30 percent off rates

I recently talked about Generator in my latest Youtube Video. 

The luxury hostel chain is offering 30 percent off rates. This is a great deal.

Generator, known for their innovative design, offers shared accommodations that are both stylish and practical. Spanning 14 properties across Europe and the U.S., these trendy “poshtels” make sure guests get the most bang for their buck with chic and adult-friendly bunk rooms – perfect for groups of friends, families, and solo travelers looking to meet new people (female-only and mixed dorms available).

Each Generator also offers private accommodations, innovative social spaces, curated programming, competitive food and beverage offerings, and central location in their respective cities. Generator has locations in Amsterdam, Copenhagen, Dublin, Berlin, Rome, Venice, London, Stockholm, Hamburg, Paris, Madrid, Barcelona, Miami Beach, and will open an additional property in Washington, D.C. later in the year.

Generator will be offering 30% off bookings from December 2 – March 28, 2020 in celebration of Black Friday and Cyber Monday, with book dates November 29 – December 2, 2019. *Reservations must be made 3+ days prior to arrival date with a 2 night minimum stay. Both sales are not applicable with any other promotions. 

Visit this link to book.

Generator Copenhagen Reception

8. Andaz Costa Rica Resort at Peninsula Papagayo in Costa Rica – 40% off rates

Here’s a great Cyber Monday deal in Costa Rica. 40% off rates are hard to come by, and Andaz Costa Rica in Papagayo is among the best resorts in the country. 

A cool tropical retreat tucked away on the 1,400-acre Peninsula Papagayo, Andaz Costa Rica Resort is launching a “2020 Flash Sale” that offers 40% off standard rates for stays of 4 nights or more. Visit papagayo.andaz.hyatt.com to book. Booking dates are from November 29-December 5 with travel dates between January 10 and December 20, 2020.

Andaz Costa Rica Resort at Peninsula Papagayo

9. The Hollywood Roosevelt in Los Angeles – 50% off rooms

If you frequently travel to Los Angeles like me, this sale at The iconic Hollywood Roosevelt hotel is pretty insane. It’s half off the room rates. This is definitely not common and worth it!

The legendary boutique hotel and entertainment industry institution is extending a very generous offer this year with 50% off Tower Suites and Cabana Rooms.

The package must be booked on Thanksgiving, Black Friday or Cyber Monday, with travel dates between November 28, 2019 and June 30, 2020. Use this booking link and promotion code: CYBERDEAL

The Hollywood Roosevelt

10. The Watergate Hotel in Washington DC – Up to 40% off

The Watergate Hotel, considered a top hotel in Washington D.C. and landmark to the famous Nixon scandal, is an urban retreat along the Potomac River. The boutique hotel has avant-garde architecture and design and retro-chic appeal, and obviously, tons of history!

From November 27 – December 3, The Watergate Hotel is offering up to 40% off room rates on all room types (excluding the Presidential Suite). Rates start at $399/night. 

History buffs will take a step back in time — to 1972 to be exact — and enjoy the glitz, glam and luxury of this iconic Great White City hotel.

Visit the website to book.

Watergate Hotel.

11. Abercrombie & Kent – up to 44% off private journeys

If you book with Abercrombie & Kent, you can save up to $3,900 (33% – 44% off) on discounted private journeys. The travel company is known for luxury voyages around the world. 

Booking windows open December 2 at 8:00am CST and close December 6 at 4:00pm CST. Select private journeys with reduced rates will cover Vietnam, India, Peru & Machu Picchu, Botswana, Moscow & St. Petersburg, Chile, Kenya, and Paris and Amsterdam.

Visit the site for details.

Some good ones include: 

Holiday Sale: Peru & Machu Picchu Private Journey – save $2,200

Seven days from $3,295 (was $5,495)

Holiday Sale: Botswana Private Journey – save $2,100

Eight days from $3,395 (was $5,495)

Holiday Sale: Kenya Private Journey – save $2,400

Eight days from $4,595 (was $6,995)

Holiday Sale: Paris & Amsterdam Private Journey – save $3,900

Seven days from $4,895 (was $8,795)

Botswana, Okavango Delta, Moremi Game Reserve, Photographing Elephants on a Game Drive. Photo: Abercrombie & Kent

12. Palace Resorts in Mexico – up to 50% off rates 

Palace Resorts with locations throughout Mexico is offering up to 50% off rack rates for Black Friday/Cyber Monday. In addition, Kids & Teens Stay Free. 

All stays (3+ nights) include up to $1,500 in Resort Credit to use on indulgent spa treatments, exotic tours, championship golf, and more. You also receive complimentary transfers to and from the airport.

Visit the website to book.

Palace Resorts adult pool



13. Booking.com – 40% off rates

Booking.com’s mission is to make it easier for everyone to experience the world by providing great value on accommodations. While Booking.com offers deals throughout the year, the savings are significant on Black Friday and Cyber Monday.

Booking.com’s sale will feature tens of thousands of deals at properties across the globe, starting at 40% off, with book by dates extending to Cyber Monday. Stay by / travel by dates until March 31, 2020, though stay dates and availability vary by property.

To search for the Black Friday deals, visit Booking.com a few days before November 29th where a banner on the homepage will lead you to a landing page that has thousands of amazing deals. Deals will be visible just a few days before Black Friday so consumers can start searching through and seeing where they might want to book, with a countdown clock to Black Friday when travelers can officially hit the confirmation button.

Nizuc Resort in Cancun, Mexico.


14. The Grove Resort Orlando – 40% off room rates

The Grove Resort Orlando is an ideal family-friendly destination with features including all-suite accommodations (up to three bedrooms!); an on-site water park with twisting tube slides, a lazy river, FlowRider, children’s activity pool; watersports and fishing at The Grove’s Lake Austin Pier; three additional swimming pools; multiple dining and drink venues; a full-service spa; and Flip Flop’s Family Fun Center with glow-in-the-dark mini golf, arcade games, and ticket redemption games.
Book between Friday, November 29 (Black Friday) and Monday, December 2 (Cyber Monday) and receive up to 40% off stays in one, two, three bedroom suites (starting rates are $115/night). Available for stays until October 31, 2020.
To book, visit groveresortorlando.com and use the code CYBER19.
The Grove Resort Orlando

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Jimmy Im has traveled to 113 countries, stayed in over 600 hotels and has flown a million airmiles. He lives in New York City.

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