25 Travel Deals to Book on Black Friday, Cyber Monday, and Beyond

Pack you bags.

Westin Los Cabos

With Black Friday and Cyber Monday upon us, ’tis the season for amazing deals…and not just on clothes, housewares, and electronics. Now is the perfect time to book your next vacation, so check out these 25 awesome travel deals that’ll take you around the U.S., Mexico, Europe, and beyond. 

1. Generator

(Photo: Generator)

With 14 properties across Europe and the United States, Generator has both private suites and hostel-style shared rooms, making for an affordable and luxurious vacation. 

The Deal: Generator is offering 25 percent off when you book two nights or more across all 14 properties, and the deal is valid for stays between November 2018 and March 2019.

Visit Generator’s website to book.

2. CheapCaribbean


As the name implies, CheapCaribbean is a travel agency specializing in the Caribbean, Mexico and Central America.

The Deal: Up to 70% off the projected top five destinations for 2019 – Dominican Republic, Jamaica, Bahamas, Los Cabos, and Cancun/Riviera Maya.

To get the deal, book a trip between November 13th and November 26th, and the deal is valid for stays now through May 2019.

Visit CheapCaribbean to book.

3. Sea Island | Georgia

(Photo: Sea Island Resort)

On the coast of Georgia, January and February temperatures average 71 degrees, and 71 percent of those days are sunny. So, Sea Island resort is having a “71” sale.

(Photo: Sea Island Resort)

The Deal: Book two or more nights for stays during the months of January and February and get 71 percent off the third night, and get complimentary offers like free breakfast for two and “golf with a pro.” 

How to Book: Visit SeaIsland.com.

4. Intrepid Travel


The Deal: Small group adventure tour operator Intrepid Travel is offering 20% off over 1,000 trips worldwide for 2019 departures. To get the deal, book a trip from November 20-28 for tours departing January 15, 2019 to December 15, 2019. 

How to Book: Visit IntrepidTravel.com/Cyber-Sale

5. The Curtain Hotel & Members Club | London


The Deal: From November 22-26, The Curtain is offering 20 percent off all room types booked for December 20 -25 and January 1 – April 22, 2019.

How to Book: Visit TheCurtain.com.

6. Hotel Commonwealth | Boston, MA

(Photo: Hotel Commonwealth)

The Deal: Boston’s Red Sox-loving Hotel Commonwealth is offering rooms for $108 starting Monday, November 26 at 1:08 p.m., for exactly 108 minutes. 

How to Book: Visit HotelCommonwealth.com.

7. San Francisco Proper Hotel

San Francisco Proper Hotel

The Deal: The property is offering a “Cyber Monday Weekend Special” through November 27 with up to 40 percent off rates on weekend stays (Friday, Saturday, or Sunday nights) for travel through February 28, 2019. 

How to Book: Visit the website – https://www.properhotel.com/hotels/san-francisco – and use the code “CYBER.”

8. Peregrine Adventures

(Photo: Peregrine Adventures/Intrepid)

Peregrine Adventures is Intrepid Group’s adventure tour operator, and they’re having a BOGO deal on three of their Asia Adventure Cruises: Cruising the Thai Islands from Phuket, Cruising Thailand & Malaysia: Phuket to Penang or Cruising Thailand & Malaysia: Phuket to Penang.

(Photo: Peregrine Adventures)

The Deal: From now until November 30th, book one of the aforementioned cruises departing December 2018 through February 2019, and you’ll get one free ticket for a travel companion (to share the same cabin).

How to Book: Call 1-800-663-5132 or chat with the Peregrine Adventures team on https://www.peregrineadventures.com/cyber-sale-bogo.

9. Hamilton Princess & Beach Club | Bermuda


Bermuda’s Hamilton Princess & Beach Club has been around since 1885, just underwent a $100 million renovation in 2016, and is only a 90-minute flight from major cities in the Northeast like NYC and Boston, so it’s perfect for a weekend getaway.

The Deal: From Black Friday through Cyber Monday, get 50 percent off on stays through March 31, 2019. Stays must include a Friday or Saturday night, though.

How to Book: Visit TheHamiltonPrincess.com.

10. Rhode Island

Go on a winter getaway or book a summer trip at these Rhode Island deals: 

Gurney’s Newport Resort & Marina 


Thirty percent off all rooms when booked between November 21 and November 25, and on Cyber Monday, get 50 percent off suites on stays between December 1 to April 30, 2019.

HillTop Inn

Book 1 night and get the second night free on stays between January 1 through March 31.

The National Hotel and Tap and Grille


For every $100 spent on gift certificates, get a $25 gift card to the Tap & Grille.

The Blue Dory and Avonlea


Get fifteen percent off gift certificates under $500, and 20 percent off gift certificates $500 or more when you purchase between November 23 and December 25th.

Spring House Hotel


Buy a $1,000 gift card and get $200 free, plus a complimentary night stay.

11. Breezes Bahamas


The Deal: Black Friday and Cyber Monday rates start at $119 per person per night at this all-inclusive resort with $10 room upgrades from now through December 31, 2019.

How to Book: Online at www.breezes.com or call 877-Breezes.

12. The Asbury Hotel | Asbury Park, NJ

(Photo: Asbury Hotel)

The Deal: Get 50 percent off all stays through May 23, 2019. The deal is available when you book between November 16 to the 25th.

How to Book: Visit TheAsburyHotel.com and use the code CYBERSTAY.

13. Angad Arts Hotel | St Louis, MO


This brand-new hotel just opened in early November and allows guests to pick a room to fit their mood, with a passionate red, tranquil blue, happy yellow, and rejuvenating green. 

The Deal: Book the “Suite Satisfaction Package” Black Friday through Cyber Monday, and get 25 percent off on stays through March 2019. 

How to Book: Visit AngadArtsHotel.com.

14. Kimpton Taconic | Manchester, VT

(Photo: Kimpton Taconic)

This boutique hotel in Manchester, Vermont, has a Cyber Monday sale that’s only going to last 112 minutes and 6 seconds.

The Deal: On November 26th from 11:26 am EST until 1:17 pm EST, Cyber Monday shoppers can book a Buy One Get One Free deal: Book one night in a deluxe room for $201.80 (a nod to the current year), and get the second night free. Valid for stays November 27, 2018, through April 30, 2019.

Plus, a separate “Cyber Monday & Giving Tuesday” deal booked from November 19 through the 30th on stays through March offers a 30 percent discount and donates $5 per night to the charities No Kid Hungry and the Trevor Project.

How to Book: Visit TaconicHotel.com.

15. Borgata Hotel Casino & Spa | Atlantic City, New Jersey


The Deal: On Monday, November 26 and Tuesday, November 27, the resort is offering special rates for Classic Rooms ($79/night) and Fiore Suites ($109/night) with no additional fee, for stays through November 26, 2018 through February 28, 2019. The offer is only valid for arrivals from Sunday through Thursday.

How to Book: Visit TheBorgata.com.

16. Refinery Hotel | NYC

(Photo: Refinery Hotel)

The Deal: From Cyber Monday until November 30, get 30 percent off rates on select dates as well as a complimentary candle and glass of wine at check-in.

How to Book: Visit https://refineryhotelnewyork.reztrip.com/classic/offers.

17. Westin Los Cabos Resort Villas & Spa | Los Cabos, Mexico

(Photo: Westin Los Cabos)

The Deal: Book a trip now through November 26 and get 35 percent off plus $50 resort credit on stays 3 nights or longer through June 30, 2019.

How to Book: Visit the website or call 877-782-0108 and ask for special rate TRVLDEAL.

18. Hotel Vermont | Burlington, VT

(Photo: Hotel Vermont)

The Deal: On November 26 only, rooms will go for $139 per night for stays from January 2 to April 30, 2019.

How to Book: Visit HotelVT.com.

19. The Cove, Eleuthera | Eleuthera Island, Bahamas


Travel + Leisure calls the island of Eleuthera “The Best Secret Island on Earth,” where this intimate 57-room resort offers tons of rest and relaxation, as well as snorkeling, paddle boarding, kayaking, and bicycling.

The Deal: Get the fourth night free and $100 resort credit when you book November 26 through November 30. The deal is available on stays between November 26, 2018, and December 31, 2019.

How to Book: Visit thecoveeleuthera.com and use the promo code CYBER.

20. The Tides Inn | Irvington, VA


This coastal Virginia inn sits on its own private peninsula on the Chesapeake Bay Wine Trail, Virginia Oyster Trail, and Virginia Artisan Trail.

The Deal: Get a third night free and $100 resort credit on stays between November 26, 2018, through December 31, 2019, when you book November 26 through November 30.

How to Book: Visit thetidesinn.com and use the promo code CYBER.

21. Enchantment Resort and Mii amo Spa | Sedona, AZ


This Southwestern resort is perfect for anyone who loves canyons, spas, and rocks. Speaking of spas, on the grounds of Enchantment Resort lies Mii amo, which was declared the “World’s Best Spa” by Travel + Leisure. 


The Deal: Get a third night free and $100 resort credit when you book November 26 – November 30. The offer is available on stays between November 26, 2018, and March 1, 2019. 

At the Mii amo spa, receive a free 60-minute treatment when you book a 4-night stay, or a complimentary 90-minute treatment when you book a 7-night stay from November 26 through November 30. This offer is available on stays between November 26, 2018, and February 28, 2019. 


How to Book: Visit EnchantmentResort.com / Miiamo.com and use the promo code CYBER.

22. Turquoize Tower at Hyatt Ziva Cancun, Mexico


Located within the Hyatt Ziva Cancun, the Turquoize tower is an adults-only section of the resort, where guests get an exclusive VIP check-in and reception area, personalized butler services, and access to the private Punta Vista rooftop bar and the tower’s gorgeous rooftop infinity pool.

The Deal: Save up to 60 percent on stays between April 29 and December 20, 2019.

How to Book: Visit https://www.resortsbyhyatt.com/turquoize-ziva-cancun.

23. Hyatt Ziva Puerto Vallarta


The Deal: Save up to 65 percent on stays between February 1st and April 2, 2019. and December 20, 2019.

How to Book: Visit https://www.hyatt.com/en-US/hotel/mexico/hyatt-ziva-puerto-vallarta/pvrif.

24. The Hilton Playa del Carmen


The Deal: Another adults-only option, save up to 65 percent on trips between January 1st and April 28, 2019.

How to Book: Visit https://www.playaresorts.com/the-royal-playa-del-carmen.

25. Panama Jack Resorts Playa del Carmen


The Deal: Save up to 60 percent on trips between February 1 and December 20, 2019.

How to Book: Visit https://panamajackresorts.com/playa-del-carmen.