The Cheapest Weekend Getaways Now are the Ones Booked for the Future

Changes in the environment require a change in tactics and that’s certainly true in the world of travel planning. As conditions change, what worked before may not work now. Finding the cheapest weekend getaways means looking at different strategies now for couples and families. You’re better off making solid plans for the future now than trying to throw together a quick vacation at the last minute. 

Grand Hyatt Baha Mar weekend getaways

Plan a weekend getaway for later in the Bahamas

When travel ground to a halt worldwide in April of 2020, a whole lot of people assumed we would lock down for a little while and then get back to normal a few months later. When it became clear that travel during Covid would be complicated for quite a while, American and Canadian vacationers found a way to get away on vacation whatever way they could. A few flew to Mexican beaches or visited one of the other open countries in Latin America,  but they were the exceptions. Most chose to take a road trip, to rent a cabin, rent an RV if they didn’t own one, or get an isolated house far from other people through Airbnb or Vrbo

Meanwhile, most hotels sat half-empty at best, especially the ones in big cities. While there have been a few bright spots in the lodging industry (mostly Cancun, hot southern states, and towns near national parks), resorts kept rolling out deals that few were willing to take. Then when they did book a hotel or resort, those couples getaway packages were ones for the coming weekend, giving management no clue as to how busy they would be until a few days before. 

Millions of people per month search “last-minute vacation deals” or “hotel deals this weekend,” but almost nobody is searching terms related to deals in the far-flung future, six months or more from now. This was true even before the travel restrictions hit, but it has only been amplified since things went south in 2020. Some hotel managers are telling us that 90% of their bookings are coming in a week or less before the stay.

As books on contrarian travel will tell you, the best way to consistently get a great deal on your travels is to take the left fork in the road when everyone else is going right, to do what you can to avoid the herd mentality. If 90% of people are trying to book their cheap weekend getaways a few days before departure, you’re naturally going to do better if you plan far ahead instead.

Yes, it feels a little riskier when the future is so unknown, but on the other hand, with vaccines rolling out as I write this and the weather at its coldest in much of the USA, you know deep down that the travel outlook is going to improve quite a bit from this low point as the months roll on. It’s just a matter of how fast that will happen.

Here are a few strategies to consider to get discounted travel on your next few vacations. Remember that nearly all vacation packages are refundable vacation packages now. Hotels have generous cancellation plans in place and  even most of the fee-loving U.S. airlines will now allow you to change your flight plans later if needed. Most of the risk is out of the equation now when you make a commitment for three, six, or nine months in the future. 

Book Trips for Places That Aren’t Open Yet

I’m starting out with what feels like the riskiest move because this is also the strategy that has the biggest potential rewards. Even if you wanted to right now, you couldn’t make a last-minute booking for Italy, or Argentina, or most of Asia. When the floodgates open again, however, and people feel safe to travel again, how long do you think it will take for people to start rushing back? 

a future vacation in Paris

I’m guessing not very long, so if you’ve always wanted to visit Paris but were put off by the prices and the crowds, start looking at options for the future and pencil in some dates. As I was writing this article, round-trip flights from Toronto to Amsterdam were going for $310, round-trip flights from the USA to Colombia or Peru were available for under $500, and I found 200+ hotels and apartments in Florence in September for under $100. 

As of summer 2021, the EU countries are open to vaccinated travelers, but visitor numbers are still low. So you can duplicate this process for Amsterdam, Barcelona, Venice, Siem Reap, or any of the other cities that haven’t had to utter the word “overtourism” for quite a while now. They’ll be very happy to have your business. 

Or is there some place on your bucket list that you’d love to see without the huge crowds? Make a bold travel resolution for the year! You could get in a plane and see Machu Picchu, the wonders of Egypt, or glorious Petra in Jordan right now, but almost nobody is taking those countries up on the open borders offer. Some nationalities can’t leave their country to travel, most others don’t feel safe doing so. Once more people are vaccinated, the numbers–and hotel prices–will start creeping up again.

Right now though, they’re a bargain. In some cases, rooms booked for late 2021 are half the price or less the rates of 2019. 

Yes I know, you don’t go to Egypt on a weekend getaway, but you can apply the same principles to places closer to home. The busiest places in 2020 were the popular drive-to destinations in the USA and Canada, so look beyond those to ones that are harder to get to in a car. Go see the wonders of Tikal, Uxmal, or Teotihuacan. Visit a Canadian national park that’s not as crowded as the southern counterparts. Fly to Liberia in Costa Rica and be on the beach or in the jungle an hour later. Stay at a luxury all-inclusive that’s discounting and throwing in extra perks, like Le Blanc or Live Aqua Cancun

View from Live Aqua Cancun resort

Or consider a city in the USA: New York hotel rates are lower than they’ve been for a decade, even six months out, as are ones from San Francisco to Miami. Every week there are lots of domestic flights for $100 or less in the USA. 

If you’re already in Europe, the cheap weekend getaways available will eventually include the great cities of Europe again. You’ll be able to hop a cheap flight or train to Prague, Venice, or Istanbul before the crowds start driving up prices again–if you lock it down soon.

Look for Future Deals on Weekend Getaways

It’s a massive understatement to say that hotels really want your business. They’ve been dangling enticing offers out there for 10 months now as I write this, so finding discounted travel has been as easy as picking your place. As long as that place wasn’t where everyone else was going, that is. It has been much tougher finding a deal in Clearwater Beach or Pigeon Forge than it has in places further from big cities and RV parks. 

Bigger is better when it comes to deep discounts, however. Country inns have had an easier time than convention hotels, for obvious reasons, beach and mountain hotels have done better than urban ones. When it gets safe to be around other people again, including ones who don’t know how to wear a mask properly, these larger properties and B&Bs will be pulling out the stops to get your business. In fact, most of them already are. 

If you think about who has been hurting the most during this travel slump, that tells you where you’ll find the hotels and resorts that really need your business. For example, many of the best cheap hotel chains in the USA rely on business travelers or attraction visitors. So do big city hotels. The giant resorts of Orlando and Las Vegas rely on conventions and masses of theme park visitors. Casino hotels rely on a steady stream of gamblers. Bahamas resorts depend on fly-in guests, Fort Lauderdale hotels depend on cruise ship passengers.

Any place where supply far exceeds demand is going to have a long list of hotels offering big discounts.  

Here are a few mid-month weekend rate examples just to give you an idea of what’s out there for hotel deals and vacation packages:

South Beach Miami in May: Hyatt Centric $180 per night double, SLS South Beach $270 with ocean view, Albion Hotel $110 per night on

Las Vegas in June: $292 per person with airfare from Chicago and 3 nights at the Golden Nugget or $332 p.p. at MGM Grand (plus annoying resort fees) on Expedia

Montreal in July: $95 double per night at Candlewood Suites Montreal, $156 at Hotel Epik, $50 at Gite du Survenant at

Amsterdam in August: $491 per person with airfare from NYC and 3 nights at Holiday Inn Amsterdam, $553 p.p. at Apollo First (4-star), or $583 p.p. at Kimpton Witt (4.5-star) at

Florence in September: Hotel Giglio $99 per night double, Palazzo Graziani $98, San Giuliano Inn $147.

Florence hotel deals

And on it goes for the rest of the year, whether it’s cheap all-inclusive vacations in the Riviera Maya, dream trips to romantic places in Europe, or a quick jaunt to Quebec City when the borders are open again. If you look now, you won’t have any problem finding weekend getaway specials, as long as you’re not going where everyone else is, like Glacier National Park or Yellowstone

This is a case, however, where investing a little research time you’d otherwise be spending watching TV can really pay off. Whether you’re looking for a cheap Caribbean all-inclusive vacation, cheap Mexican vacation packages, or a one-price deal for your whole stay in Florida, you’ll need to shop around on various sites. All of the online travel agency websites are desperate to get your business now and so are the lodging companies they serve, so they’re all trying to outdo each other to provide whatever will get you to hit the “book now” button.

If you’re not looking for a vacation package deal, use Google Flights or Skyscanner to find the best flight deals from your own airport, then search the lodging options. 

Rack Up Hotel Loyalty Points for Free Stays

While this pandemic has been raging, my accounts have been getting richer–and I’m not talking about my retirement funds. I’m talking about my point balances with the hotel chains. I belong to most of the hotel loyalty programs since that gets me free WiFi at the corporate hotels, but for three of them, I earn points through credit card spending as well. I can transfer points to Marriot Bonvoy via my American Express card, I have another Amex card for Hilton, and I have a Chase Mastercard tied in to IHG Hotels

I’ve expanded my balance with all three programs since the lockdowns started, despite limited travel. I put recurring bills on them for a start. Then they’ve all been offering big bonuses to anyone paying attention to their e-mails. I’ve gotten 5X points on gas and groceries, bonuses on points transfers, bonuses for ordering food from the right local businesses, and a 1,000-point bonus for using my new version of the card that I can tap on store’s processing machine instead of inserting or swiping. IHG even offered a 10,000 point bonus for one stay at any of their properties in December, so I booked a one-night stay near where I live and earned more than 12,000 in the end—easily enough for a free night’s stay in the future. 

Some of these cards give you a free night’s stay in your bank each year upon renewal as well, so if you pay an annual fee, you’re actually getting something out of the deal. Before you know it, you’ve got enough points for a weekend getaway saved up. Or if you’re getting a sign-up bonus at the beginning, you might earn enough for a whole week! 

save hotel loyalty points to cash in later

If you’re banking points now while you’re not traveling, you’ll have a lot to cash in when you are. 

The Cheapest Weekend Getaways for Procrastinators (or the Spontaneous) 

If you’re not comfortable making long-term plans right now, you should at least read this article about how just planning a vacation can elevate your mood and give you something to look forward to. Maybe it will change your mind. 

If not, you can still book that last-minute all-inclusive vacation or that romantic Colorado weekend getaway in the mountains. The booking sites will still be ready to serve up something tempting for you. Here are a few links to start with to find nearby deals you can drive to or ones to open places where you can fly. 

Last-minute deals from Travelocity

Weekend package deals from Expedia

Based in Europe? Try the appropriately named

Hotwire is the long-running champ for last-minute hotel deals, as long as your plans are solid. 

last-minute hotel deals for cheapest weekend getaways

Keep in mind that if you do travel abroad and you’re American, you now have to get a Covid-19 test with negative results before you head home. Most of the international hotels are on the case with this though, so you can probably get it done without even leaving the resort. Otherwise, since a rapid test is accepted on the return, you can get tested at the airport for a fee. Just arrive earlier than usual. 

When you’re ready to take off again, don’t wait too long to commit. Five years from now, we’ll be looking back at this time and saying, “Remember when you could find great travel deals to almost anywhere on the planet?” This is a strange event that happens once in a lifetime. We’ve suffered greatly from the dark side of it, so be sure to take advantage of the silver lining: historic weekend getaway bargains. 

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