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15 Can’t-Miss Columbus Day Weekend Travel Deals You Need to Book

Whether you're looking for the last gasp of sun and surf before winter starts, a fun city getaway, a steamy desert weekend by the pool, or hiking in the crisp, cool mountains, we've got the travel deals for you.

Every editorial product is independently selected, though we may be compensated or receive an affiliate commission if you buy something through our links.

the-naples-beach-hotelvia tripadvisor.com

Naples Beach Hotel & Golf Club

If you’re looking to head down to Florida for Columbus Day weekend, The Naples Beach Hotel & Golf Club is offering a special fall savings deal from October 1 through December 21. The AAA Four-Diamond resort is giving its customers a 20% discount off accommodations for stays of one or two nights and 30% off for stays of three or more nights. During your visit, you’ll get to enjoy the lush 125-acre resort which sits directly on the beach, the in-site championship golf course, world-class spa, and tennis center.

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restaurantvia tripadvisor.com

 Renaissance Denver Downtown City Center Hotel

This historic hotel in the heart of downtown Denver is offering a way to stay Columbus Day for free. Since the hotel is located in Denver’s former Colorado National Bank Building they offer a free night on all banking holidays—Columbus Day being one of them. Rates start at $189 and if you book their Coming Up Daisies Anniversary Package, to celebrate their five year anniversary, you’ll get a few extra perks such as Columbus Day free, in-room daisies, valet parking, a complimentary cocktail, and a historic tour of the building. You won’t be able to pass up these secret travel deals.

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roof-garden-terrace-fugavia tripadvisor.com

Casa Delphine in Mexico

If you want to squeeze in a quick tropical trip before winter starts up this boutique hotel right outside the heart of San Miguel de Allende is the perfect place to visit. Their spacious suites feature Cantera fireplaces hand-designed furniture from local artists, warm accents, eclectic textures and colors and balconies that overlook the private courtyard and more. If you book two nights you’ll get the third at a 30% discount. This offer is valid until the end of October and rates start at $265 per night.

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frolik-kitchen-cocktailsvia tripadvisor.com

MOTIF Seattle, a Destination Hotel

Guests staying at the MOTIF Seattle can enjoy newly renovated rooms with views of the city skyline, Olympic Mountains, and more. It sits at a crossroads between shopping, stunning landmarks, Seattle sports teams, and music from past and present. The best part, if you book two weeks in advance you can save up to 20% off rooms.

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othervia tripadvisor.com

Wailea Ekolu Village, by Destination Residences Hawaii

Use promo code COUNTDOWN to save up to 34% on a one-bedroom villa that features a plush king-sized bed and enviable views of the Big Island at this Maui hotel. The 18-acre resort features villas and panoramic views of the beautiful Pacific Ocean and Kahoʻolawe Island. Also, book these last-minute winter travel deals for 2019.

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receptionvia tripadvisor.com

Conrad New York Downtown

Travelers can take advantage of the Long Weekender deal and can save up to 50% off if they stay Sunday night after also booking a stay for Friday and Saturday nights. The contemporary-style hotel offers views of the Hudson River, and downtown Manhattan. Guests can also enjoy the one of a kind seasonal rooftop bar and lush garden.

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recreationvia tripadvisor.com

Marriott Marquis Houston

If you’re traveling to Houston for college football over Columbus Day weekend you’ll want to stay at the Marriott Marquis. They’re offering the perfect package to help you cheer on the University of Houston Cougars during their home game. The UH Coogs package includes an overnight stay at the hotel, reserved seats for two at elevated, bi-level sports bar, Biggio’s to watch the game, a bucket of five domestic beers, and a party platter of wings, nachos, and pretzels. Package rates begin at just $209.

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breezes-resort-spa-bahamasvia tripadvisor.com

Breezes in the Bahamas

Since tourism is the backbone of the Bahamas, Breezes Bahama is offering rates at a 53% discount to help rebuild the islands after being hit by hurricane Dorian. Located in Nassau, Breezes wasn’t hit as bad. Travelers can score rooms for as low as $168 per night from October 1 through November 6. At the only super-inclusive resort in the Bahamas, guests can enjoy a number of land and water activities along the white sand beaches.

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suite-2via tripadvisor.com

Loews Philadelphia Hotel

Loews is offering a special Visit Philly Package that you can enjoy over Columbus Day weekend. Book your stay between September 12 and November 30 to get free overnight parking, free tickets to The National Constitution Center and the Museum of American Revolution, a Garces restaurant card, and free all-day passes for the Philadelphia PHLASH Downtown Loop. These off-season travel deals will save you big bucks.

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allegro-playacarvia tripadvisor.com

Allegro Playacar in Playa del Carmen, Mexico

At Allegro Playacar guests can relax by the pool or ocean and enjoy unlimited meals, snacks, and beverages from three restaurants and three bars, along with sports, water activities and a disco. If you book for travel between now and January 1, 2020, you can get up to 49% off all bookings. Rates start at $282.

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hopkins-bay-resortvia tripadvisor.com

Muy’Ono Resorts’ in Belize

Two of Muy-Ono Resorts’ properties—The Placencia and Hopkins Bay Resort—are offering 20% off rates and complimentary breakfast during the month of October. The perfect excuse to travel over Columbus Day weekend. If you’re traveling with family, Hopkins Bay is a good fit. You and your family can climb ancient Maya ruins, canoe or kayak on Belize’s jungle rivers, go birding through the rainforest, or just unwind and relax under the tropical sun.

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ogunquit-resort-outdoorvia tripadvisor.com

Meadowmere Resort in Ogunquit, Maine

Take in gorgeous fall foliage and crisp New England air on the coast of Maine over Columbus Day weekend. If you’re staying for two nights, you can get a rate of $186 per night with breakfast included with booking code VALUE. If you’re staying for three nights, you can get the dining package which includes a  wine and cheese welcome, breakfast, dinner at your choice of Ogunquit’s best restaurants, and a late check out for $193 a night with booking code HOLIDAY. Here’s how you can take your dream vacation on the cheap.

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lobby--v17854823via tripadvisor.com

Hotel Chimayo in Santa Fe, New Mexico

In Santa Fe, they refer to the holiday as Indigenous Peoples Day and they celebrate the Native American Pueblo people and cultures of New Mexico in lieu of Christopher Columbus. Over the holiday weekend, they are offering a Palace of the Governors package and a Getaway Before the Holidays package that can get you up to 30% off your stay.

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desoto-beach-hotelvia tripadvisor.com

Desoto Beach Hotel on Tybee Island

The Desoto Beach Hotel on Tybee Island in Georgia has some great deals running over Columbus Day weekend. To get 15% off per night use the code “Vtyb15f19.” The cost for a two-night stay depends on the type of room but averages between $570-$580. This hotel allows for easy access to downtown and direct access to the beach.

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suitevia tripadvisor.com

The Confidante Miami Beach

This playful oceanfront oasis is offering a third-night free fall promotion for Columbus Day weekend. Guests will love getting away for the weekend in this 1950s-inspired designed hotel. When guests book three nights, they receive their third night free for stays between now and October 31—more than 30% savings! To help you book your trip for other months, check out the best weekend getaways in every state.

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Morgan Cutolo
Morgan is the Assistant Digital Managing Editor at Reader’s Digest. She graduated from the University of New Hampshire in 2016 where she received her Bachelor of Arts in Journalism. When she’s not writing for rd.com or keeping the 650+ pieces of content our team produces every month organized, she likes watching HGTV, going on Target runs, and searching through Instagram to find new corgi accounts to follow.