Cyber Monday Travel Deals: Hotels, Resorts, Cruises, and Tours

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Black Friday has come and gone, but Cyber Monday deals are still in full swing. If you’re wondering whether there are really any good travel deals out there, considering all the ups and downs the tourism industry has faced in the past few months due to the pandemic, this list proves travel companies are still offering plenty of discounts. From ski lodges in South Dakota to safari trips in Kenya, keep reading for the best offers that stood out to us, including Cyber Monday travel deals at many of our Readers’ Choice Award winners.

All listings featured on Condé Nast Traveler are independently selected by our editors. If you book something through our links, we may earn an affiliate commission. This article was originally published in November 2020. It has been updated with new information.

Domestic hotel deals

Hotel Vermont

On Cyber Monday, Hotel Vermont—a three-time Readers’ Choice Award winner—rooms will be available to book at a special rate of $159 per night. That includes a welcome drink for two at Juniper, the Burlington hotel’s bar and restaurant. Stays must occur between January 1, 2021, and April 30, 2021.

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Sea Island

With five miles of private beach, picturesque salt marshes, and a bevy of outdoor activities from golf to tennis to horseback riding, Georgia’s Sea Island resort is an ideal spot for a socially distanced getaway. Through November 30, the four-time Readers’ Choice Award winner is offering a stay two nights, book the third night for $20 deal at both The Lodge and The Cloister for travel between December 1, 2020, and February 28, 2021.

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Gurney’s Montauk Resort & Seawater Spa

A Traveler reader favorite, Gurney’s Montauk Resort & Seawater Spa sits on a beautiful stretch of beach in the Hamptons. Through November 30, take up to 50 percent off rates at the resort for travel through the end of 2021—more specifically, 30 percent off of standard rooms, 40 percent off of suites, and 50 percent off of cottages. (At Gurney’s Newport location, take 40 percent off hotel rooms and 50 percent off suites.)

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Ace Hotels, U.S.

Our readers love the Ace Hotel—so much that it made it to our list of the best hotels in our 2020 Readers Choice Awards. You can book a room at any participating Ace hotel (Chicago, DTLA, New Orleans, and Palm Springs) and get up to 50 percent off its best available rates. The booking link went live on Friday, November 27, and closes on November 30. All offers will be available for stays booked through August 31, 2021. The hotel’s gift shop will also offer discounts on all shop items and free shipping with the code FREE4USPS.

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What’s the overview of this place?
Hotel Commonwealth’s combination of Colonial style and modern design feels distinctly Boston, and its proximity to Boston University, Fenway Park, and the Museum of Fine Arts makes it a no-brainer for visitors.

What’s the crowd like?
Kenmore Square is one of the busiest parts of Boston, so you’ll see a mixed crowd: B.U. parents, Red Sox fans, and business travelers looking to take advantage of the neighborhood’s exceptional dining.

Tell us about the rooms.
The design ethos here is a modern take on classic New England. There are wood accents and neutral colors, as well as dramatic upholstered headboards and houndstooth pillows. The rooms are quite spacious by Boston standards, and feel totally livable, especially with the comfy Serta Perfect Sleeper pillow-top beds.

How about the little things, like the mini bar, or the shower goodies?
Google Chromecasts are a nice touch, and the Italian linens and plush down comforters are especially cozy. Make sure to ask for extra Apotheke bath amenities so you can bring them home.

Can we eat here, or are we better off venturing out?
With Eastern Standard, Island Creek Oyster Bar, and The Hawthorne all on the premises, there’s no shortage of excellent options, even if all you can muster is ordering room service.

How about the staff? Was there anyone who really impressed you?
The valet staff make check-in seamless. Someone will grab your bags from the front door and deliver them to your room before you’ve even finished at the front desk.

Anything stand out about other services and features?
Hotel Commonwealth is extremely pet friendly, offering walking, grooming, and sitting services. The hotel has a great gym and valet parking, too—although the latter comes at a price.

Bottom line: Why are we booking here?
This hotel has exceptional service, elegant (yet not too precious) accommodations, and some of the best food and booze in Boston.

Hotel Commonwealth, Boston

We love this 2020 Reader’s Choice Award winner for its Colonial style and modern design feel, which just about sums up Boston. This year they are welcoming all guests to a stay safe, stay longer, staycation promotion. The rate per night will be $106, including overnight accommodations in a spacious guest room, complimentary on-site parking ($58 value), and a 6 p.m. late check out. The booking link opened at 6 a.m. on Friday, November 27, and closes at 6 p.m. on Monday, November 30. Make sure to use the code Cyber6 at checkout.

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The James New York, NoMad

Located near the iconic Madison Square Park and steps away from the Flatiron district lies this quintessential four-star hotel. This year they have launched their biggest savings promotions, which includes up to 50 percent off their best rates. Book now until December 7, 2020, for stays from November 23, 2020, through December 31, 2021. 

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Terry Peak Lodge, South Dakota

South Dakota has become a trendy destination thanks to being home to numerous National Park Service units and endless historical sites like Mount Rushmore and the Badlands. So you’ll want to take advantage of this Terry Peak Lodge deal. From private cabins to ski resorts and hot tubs, it’s a real paradise for ski lovers. Get 30 percent off two-night stays between now and until March 15, 2021. This promotion went live Friday, November 27. To secure a spot, you must call a Black Hills Travel specialist at 800-229-9019.

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The Setting Inn Napa Valley, California

This three-star hotel is a boutique, historic landmark that sits in the heart of the California wine country. Guests can enjoy wine tastings, spacious rooms, and a serene landscape filled with lavender and maple nut trees around the one-acre property. Book three nights and receive 30 percent off your entire stay. If you book a cottage, you will also receive a $100 credit at Bottega and a $100 transportation credit with Beau Wine Tours. Rooms will be available to book starting Friday, November 27 and running through Monday, November 30.

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Encore Resort at Reunion, Florida

The Encore resort is one of the best places to stay in Central Florida when vacationing with family and friends. From all types of vacation homes, experiences (including free transportation to and from Walt Disney World), you’ll find something best suited for everyone’s needs. You can receive up to 30 percent off all booking rates and a one-time $100 resort credit. And since all travel plans can be a bit stressful during these unprecedented times, all cancellation fees will be waived. Use the code THANKFUL2020 at checkout.

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Miraval Resorts, Texas

Miraval Resorts and Spas are secluded and private luxury destinations that work to replenish your spiritual health and promote wellness experiences. They are offering savings at their three properties in Arizona, Austin, and their newest location in the Berkshires for the holidays. Starting from November 30 to December 7, guests who book a stay will receive $275 nightly resort credit per person. The credit can be used on your choice of spa services, activities, and private sessions. Best part? There are no room type restrictions, so you can even splurge on a private luxury villa.

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Shop Expedia’s nine days of deals now through December 1 to get up to 50 percent off select hotel stays. You have until September 21, 2021, to travel, and there are plenty of domestic hotels available, including Traveler-reviewed spots like Arthouse Hotel in New York, The Huntley Hotel in Los Angeles, and Monarch Beach Resort in Dana Point, California.

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International hotel deals

Kimpton Hotels

Kimpton’s many hotels are a regular in our annual Readers’ Choice Awards, whether they’re situated in Phoenix, Arizona, or Amsterdam. Through December 7, the hotel group is giving travelers the chance to take up to 25 percent off its Best Flexible Rate, and donating $5 from every booking to No Kid Hungry. Stays can take place from November 25, 2020, to September 7, 2021, with dozens of locations participating (Key West, Santa Barbara, and San Diego included).

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Radisson Hotels

As a part of the ‘Deal Days: Super Sale’ promotion, Radisson Hotels will offer all guests who book two or more nights 25 percent off (non-Radisson Rewards members) or 30 percent off (Radisson Rewards members) their stay at participating locations throughout the United States, Canada, Latin America, or the Caribbean. The sale will last through December 2, 2020. Best part? The deal is also valid for holiday stays between December 14, 2020, and December 31, 2021.

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Hilton Aruba Caribbean Resort & Casino

Book five nights or more at the Hilton Aruba Caribbean Resort & Casino, and you will receive a complimentary breakfast. The Hilton Aruba will also donate $25 per night of the room rate to a local organization your choice through the Give Back Aruba initiative. Offer dates are valid now through June 30, 2021, with a 14-day advance booking required. 

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Karisma Hotels & Resorts, Mexico

If you’re planning a trip to Mexico soon, you’re in luck. Karisma Hotels and Resorts has launched their biggest mystery Mexico sale with 80 percent off all-inclusive rates that start at $99 per person per night. The sale lasts through December 5, 2020.

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Hamilton Princess & Beach Club, Bermuda

Dubbed the “Pink Palace” for its rose-colored hue exterior, we love the Hamilton Princess & Beach Club, and so do our readers who have kept it on our Readers Choice Awards list for four consecutive years. If you are looking for a getaway to the Caribbean, now’s a great time to take advantage of this promotion—the hotel offers 40 percent off all stays booked between now and December 31, 2021. Be sure to use the code PBLK when booking. 

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Secret Bay, Dominica

We love this 2020 Readers Choice Awards winner because who wouldn’t want the chance to live out their castaway fantasies (with outstanding accommodations)? If you book a stay by December 2, you’ll receive 40 percent off the best available rates. The offer also includes a local rum nightcap delivered to the guest’s villa each evening, 60-minute couples signature massage, private roundtrip airport transfers, a daily organic breakfast basket, and a dedicated villa host. Rates start at $710 US/night, inclusive of taxes. Send an email to [email protected] to book.

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Rosewood Hotels & Resorts

The Rosewood Hotels and Resorts just launched a brand-wide Black Friday promotion and will offer 40 percent off bookings through December 1, 2020 at 11:59 p.m. EST. This offer will also be valid across all of the hotel group’s properties throughout Europe, Asia, the Middle East, and the Americas. These offers will only be applicable for trips booked now until June 30, 2021.

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Casa De Campo Resort & Villas, Dominican Republic

Another winner on our 2020 Readers Choice Awards list, this hotel lives up to its reputation as a millionaires paradise and frequently hosts VIP guests. Guests who book an Ocean Front Villa for three nights or more (starting at $2,499 a night) will receive a $1,000 resort gift card as well as exclusive experiences. These include a private dinner prepared in-villa for up to 10 people, private golf lessons, private shooting lessons for two, and more. Additionally, guests can save up to 50 percent off of rooms & villas with an additional $100 resort credit on stays of three nights or more when they book directly with the resort. Reservations can be made online or by calling (888) 567-1355.

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Train, Flight, Car, and Tour Deals


Amtrak’s Track Friday Sale returns this year with up to 50 percent off select routes, including one-way Acela tickets between New York City and Boston for as low as $49. For more on Amtrak’s sales, head here.

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Starting today and throughout the entire weekend (and into Monday), Priceline will have more than 60 deals active across hotels, flights, and rental cars. There will be a combination of discounts available to all customers with exclusive deals for Priceline VIP members and Email Insiders. You can expect flight deals for up to 50 percent off and hotel coupons for up to 60 percent off savings.

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Expedia, cars

Through December 1, Expedia is also offering deep discounts on car rentals. Top deals come from Avis and Budget rentals, both up to 30 percent off, followed by Dollar car rental with up to 20 percent off. If your plans are tentative, you can rest easy thanks to free cancellations across the board.

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Lion World Travel, safari

If you’ve ever dreamed of taking a safari trip to Africa, now’s your chance. Lion World Travel has released early Black Friday promotions you can book directly in Tanzania and Kenya. The Classic Tanzania safari has a savings of $1,000 per couple ($500 per person on specific dates between March and May 2021). There will also be no single supplement fee, including international airfare, meals, and private experiences. Travelers must book by December 17 for exclusive pricing and airfare.

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Book safaris in Tanzania now:

Trafalgar, vacation packages

Trafalgar is offering savings up to $1,000 for guests traveling worldwide and up to $300 off flights. Guests can choose from various Trafalgar’s ‘Best Of’ worldwide trips, including Best of Italy–a sojourn through the region’s cities, lakes, and coastlines. Travelers will get to learn the delicate art of glassblowing in Venice, ascend a private Vatican spiral staircase, and dine with locals on Isola Madre Island—all at a reduced price. The itinerary includes transportation, accommodations, a Travel Director, local specialists, local-focused meals, and more. Visit their site for a complete list of applicable trips.

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Cruise deals


MSC Cruises is a Swiss-based European company that has become known for its year-round Caribbean and Mediterranean itineraries. This year cruisers booking the Black Friday deal will get to save up to $600 off cruise fares, up to $200 onboard credit, and up to $600 extra savings with Kids Sail Free on 2021 cruises in the Bahamas, Caribbean, Mediterranean, or Northern Europe. These deals will be available for booking starting Wednesday, November 25 until Tuesday, December 1.

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Azamara is launching its first ‘Thank You Sale’ this year. Guests can enjoy up to $1,000 onboard credit and complimentary two-category stateroom upgrades when they book between November 19 through December 5. You can choose from endless experiences like exploring Dublin’s Celtic history and making your way through Norway’s beautiful Fjords. 

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Virgin Voyages

The Virgin Voyages Thanksgiving promotion is one you won’t want to miss. From now through November 30, every person who books a trip will receive up to $400 in onboard credit (which can be used on pretty much anything). The offer will go live starting Wednesday, November 26, and will be available to use on all new bookings, including the Sailors and First Mates tiers.

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Norwegian Cruise Line

It’s that time of year again when Norwegian Cruise fans will get the chance to take advantage of the brand’s biggest deal of the year. The Black Friday sale includes 30 percent off of voyages on any ship visiting more than 300 destinations worldwide. Plus, if you book during the promotion, guests will be entitled to all five free at Sea offers, which include all the following; open bar, specialty dining, shore excursions, Wi-Fi, and discounted rates for friends and family. This offer applies to all departures and itineraries with dates in 2021 through the newly released 2023 itineraries (Bermuda, the Mediterranean, and Europe).

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For more Black Friday/Cyber Monday cruise deals, head here.

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