Seven Cheap Romantic Getaways

With the thick of winter upon us and Valentine’s Day right around the corner, you might be dreaming of an impromptu getaway with the one you love. But where will you go?

Perhaps you’re craving a relaxing weekend at the beach. Or, maybe you’d rather do something active and exciting. Either way, the world is your oyster – provided you can afford it.

If you’re on a budget, planning something over-the-top probably seems out of reach. But dig a little deeper and you’ll find a ton of cheap and easy options that are both romantic and budget-friendly. Depending on where you live, you might want to give these ideas a whirl. Just remember that taxes and additional fees may apply, and that you should always read the fine print.

In this article

    The Cheap Beach Retreat

    Is there anything more romantic than the waves crashing at your feet? Or sitting on a beach balcony sipping champagne by moonlight? Sounds like it would be expensive, but it doesn’t have to be. If you want to save, get creative.

    Instead of going for the traditional hotel experience, browse Airbnb or HomeAway for a vacant condo, bungalow, or apartment you can rent on or near the beach. Not only will you get more room and character than you would from a hotel, but you’ll also have a kitchen at your disposal — so you can save money by preparing a few meals at home instead of dining out for every meal.

    For example, check out this oceanfront Marco Island, Florida condo, complete with amazing sunset views, and for $129 per night. This charming beach condo in San Diego is also a winner, not only because it’s just 50 steps from the sand, but because it has a living room, dining room, and kitchen in addition to a cozy bedroom.

    The key to choosing a cheap beach retreat is (hopefully) finding a destination within driving distance so you don’t have to splurge for flights. For that reason, make sure to check out lakefront and riverfront properties if you don’t live near the ocean. This lakefront rental RV in Minnesota may not have lapping waves, but it comes with gorgeous water views and it’s only $90 per night.

    Off-Season Culture

    During the cold winter months, most folks are hitting the ski slopes or packing up for warmer climates. Going against the grain can help you score great prices in popular cold-weather cities such as New York, Boston, or Chicago. After all, while the cold temperatures will keep the crowds away, the world-class restaurants, theaters, and museums in these cities don’t shut down just because it’s chilly out.

    • New York: A night in the Big Apple can make you feel like you’re living in a movie. Check out for epic deals at a wide range of New York properties — rooms in Times Square can go for as little as $85 per night.
    • Chicago: offers the best deals at hotels in downtown Chicago, with rooms on the magnificent mile and right downtown starting at just $100 per night
    • Boston: Groupon has plenty of hot (and romantic) deals on hotels in downtown Boston, including a stay at the Boston Park Plaza Hotel for just $99 per night. Meanwhile, rates at the historic Omni Parker House in the heart of downtown Boston, where John F. Kennedy held his bachelor party, start at just $109 per night.
    • Toronto: What’s more romantic than whisking your partner away and out of the country? lists a ton of Toronto hotels featuring hot deals for these cold weather months. For example, rooms at the Holiday Inn Tortonto Downtown Centre start at just $87 per night. What’s more, the favorable exchange rate means everything is priced at a built-in discount.
    • Miami: Cultural hub Miami boasts an array of deals that are good for winter months. Check out for Miami hotels that start at $44 per night.

    The Caribbean Without a Passport

    If you’re itching for something tropical but don’t yet have a passport, consider a cheap romantic getaway to the U.S. territories of St. Thomas or St. John. While both suffered some damage from hurricanes Irma and Maria, they are reopened for business and eager to get tourists back on their shores.

    Fortunately, visiting either U.S. territory can be fairly affordable and rather convenient. Not only will you save an average of $125 per person by not splurging for a passport, but you’ll avoid the hassle of customs and find affordable (often nonstop) flights from many East Coast airports.

    St. Thomas is a haven for both lovebirds and adventure-seekers. The island features gorgeous beaches, a great cruise port perfect for shopping, and plenty of recreational opportunities. You can see amazing wildlife at Coral World Ocean Park, rent kayaks or snorkel gear, or sign up for one of the many romantic sunset cruises offered on the island. St. John, on the other hand, is ideal for nature lovers. Made up mostly of protected park land, the island offers a feeling of seclusion you can’t get elsewhere in the Caribbean.

    While there are tons of hotels to rent in both St. Thomas and St. John, one of the least expensive ways to plan this getaway is to rent a condo. On gorgeous Sapphire Beach, you can get a beachfront, walk-out condo for just $144 per night, for example. While you’ll have to pay cleaning fees and potentially a booking fee, you can save money by cooking your own meals in your beachfront kitchen.

    The All-Inclusive Couples Getaway

    If you already have your passport in hand, an all-inclusive trip to the Caribbean is just a plane ride away. All-inclusive resorts are like other resorts, except for one huge detail: Your meals, drinks (usually even alcohol), tips, snacks, and entertainment are all included for one price. This can lead to huge savings if you take advantage of everything an all-inclusive resort has to offer, and it certainly makes your trip easier to budget for.

    What really surprises people is just how affordable all-inclusive resorts can be. If you’re willing to book in the Dominican Republic, Jamaica, or Mexico, for example, you might see prices as low as $900 per week per person –including the cost of your flight. is an excellent place to shop around for the best price, as is For an example of the deals that are out there, consider this four-night trip with air to the Riu Montego Bay for $809 per person. That rate includes airfare from a number of U.S. cities, plus on-site entertainment and all you can eat and drink. Heck, it even includes supervised daycare at the on-site kid’s club.

    Also keep in mind that there are plenty of all-inclusive hotels you can book with points if you have them. If you have the Hyatt Credit Card or a premier Chase travel credit card, for example, you can book an all-inclusive stay at an adults-only Hyatt Zilara property in Mexico or Jamaica for just 20,000 – 25,000 points per night.

    A Romantic Cruise

    Cruises are one of the most affordable getaway options out there, and some of the shorter itineraries can be both affordable and romantic.

    For example, a seven-night Caribbean cruise out of Miami starts at just $499 per person on MSC Cruises. When you consider the fact that cruises include most or all of your lodging, food, and entertainment, that’s one heck of a value.

    Just picture yourself on the deck of the gorgeous new MSC Seaside, which had its inaugural launch in December of 2017. For just $499 per person, you’ll cruise seven days and six nights with stops in destinations like Nassau, St. Thomas, and Antigua. On days when you’re not at port, you can relax on the pool deck, catch some rays, and finally dive into that pile of books you’ve been collecting.

    Since most of your expenses are included, cruises offer a great way to enjoy your loved one without breaking the bank — or going over budget. But if you’re looking for the best deals, make sure to shop around. In addition to other online booking sites, offers huge discounts on dozens of cruises that haven’t sold out. You can even save up to 82% on last-minute cruises with the 90-day ticker.

    Prices vary depending on where you live – and which cruise port is closest to your home. The good news is, the vast majority of Americans live close enough to a cruise port to drive, and that could mean additional savings on airfare.

    The Winery Weekend

    You can find wineries in all corners of the U.S., including some unlikely places like Upstate New York or Michigan. For example, Finger Lakes Wine Country in New York offers several packages that include lodging, breakfast or lunch, and access to an area winery. Prices start at $200, and discounts increase steadily the more nights you stay.

    Meanwhile, Chateau Chantal in Northern Michigan offers several wine-themed getaway packages for couples for as little as $30 on top of the standard room rate.

    If you live near the West Coast and want to try something different, the Napa Valley Wine Train offers all-inclusive overnight stays to a number of the region’s wineries. For example, its Hilton Garden Inn “Wine, Dine and Dream” vacation package includes one- or two-night stays at the Hilton Garden Inn, a gourmet lunch on the train, and two-for-one tastings at select wineries with the “Taste of the Valley” pass. Prices start at $349 per night per couple.

    The Outdoor Escape

    You may live near a state or national park, but that doesn’t mean you’ve ever been. A cheap weekend in a cabin, camper, or tent may not invoke the idea of romance to you, but it will definitely get you away from the distracting hustle and bustle of everyday life. And if you’re looking for a cheap romantic getaway, well, getting away on the cheap is two-thirds of the goal. There’s no reason you can’t add the romance part yourself.

    If you or your spouse are the outdoorsy type, look for winter deals in the mountains. Sure, the big ski resorts are expensive, but there are less pricey ways to have fun in the snow.

    For example, the Appalachian Mountain Club in New England offers winter deals in their mountain lodges, where you can enjoy free winter sports like cross-country skiing or snowshoeing; they also offer lodging and skiing packages. Minnesota’s Lutsen Mountains area offers “Ski and Stay” packages for as little as $139 per person for two nights.

    If you live out west, a trip to skier’s paradise Jackson Hole, Wyo. may even be in order. Jackson Hole Mountain Resort is now offering “Ski Free, Stay Free” packages that include free lift tickets, discounts on lodging, and even savings on airfare if you need it. If you want to check out the weather and ski conditions first, check out one of the resort’s live webcams for a nonstop view.

    What is your favorite cheap romantic getaway?

    Holly Johnson

    Contributing Writer

    Holly Johnson is a frugality expert and award-winning writer who is obsessed with personal finance and getting the most out of life. A lifelong resident of Indiana, she enjoys gardening, reading, and traveling the world with her husband and two children. In addition to The Simple Dollar, Holly writes for well-known publications such as U.S. News & World Report Travel, PolicyGenius, Travel Pulse, and Frugal Travel Guy. Holly also owns Club Thrifty.