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Expert Tips for Your Next Vacation Rental


Vacation rentals are hot right now, thanks largely to accompanying perks that meet traveler’s demands: affordability, convenience, and amenities like kitchens, more space (for both small and large groups), and accessibility. The value of a vacation rental versus a hotel room is significant: rather than paying for two hotel rooms at a steep rate, a family of four can stay in a multi-bedroom rental that not only reduces the cost per guest but gives the family greater control over spending and amenities. They can cook their own breakfast, do their own laundry, and, depending on location and season, have their own swimming pool.

"The best part," says Bob Milne, President of Wyndham Vacation Rentals, North America, "is that travelers still have many of the hotel-like services with the convenience of a rental. Since our rentals are professionally managed, we have 24/7 customer service, and many properties have on-site offices and concierge programs."

While vacation rentals have been dominant in Europe, their popularity is beginning to rise in the US. To maximize your winter (and spring and summer) getaways, we compiled some expert tips on getting the best vacation rental.

How to Book a Vacation Rental

Just like booking engines for hotels, plenty of web sites offer the convenience of booking their vacation rental online. Sites include managed by and owned by, though Wyndham Vacation Rentals has the motherload, offering more than 95,000 vacation properties in over 500 destinations. Wyndham is unique as the company works closely with property owners so you don’t have to. offers diverse accommodations and allows renters and visitors to work directly with each other on rentals (though they do charge a fee per booking).

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When you finally arrive at your rental, make sure you know beforehand how to receive keys. Most rentals will handle keys in a pre-arranged location, whether a drop box, management office, or in-person.

What to Look For

Every site allows visitors to filter through searches. It’s best to decide your destination and date, then let the web sites do the grunt work for you. All the sites offer a breakdown of vacation rental options with detailed amenities, traveler reviews, and, often, the option to compare with another rental.

After you’ve chosen your destination and date, then you can have fun narrowing down your wants while keeping in mind your needs. If you have a small child in a stroller, you’ll want to make sure that condo has an elevator, or if you’ll need to check in on work at least once on your trip you’ll want to make sure that cute beach bungalow has WiFi. Likewise, take a look at nearby services—your chosen rental has a great kitchen but the nearest grocery story is…how far away?

What You Can Expect to Pay

The prices of vacation rentals depend on the size, location, and amenities offered. For instance, a rental with a private pool or hot tub will likely be more costly than one without. The more amenities offered, including the rental’s location to shops, restaurants, and attractions, the higher the cost. But those are obvious. The real key is to look into the market and season.

Tennessee’s Great Smoky Mountains National Park, America’s busiest national park, has more vacation rentals than it does hotels (Wyndham alone offers more than 400 cabins and condos) but the destination is perfect year-round, so prices reflect that. Vail is popular during ski months, so expect to pay a little more than during summer. There’s high demand in Charleston, consistently voted one of the top destinations in the US, so expect higher prices than, say, Sun Valley, Idaho.

Many sites offer deals and special offers for popular destinations, whether for non-peak seasons or popular destinations where rentals have yet to be booked.

When to Book

Like hotels, prices of vacation rentals will increase with demand and reflect seasonal and holiday rates. It’s best to book as early as you know your dates of travel, often months in advance. Ski season is upon us in Vail, Park City, and Stowe, while sun-worshippers are already counting the days until their Florida trips. Those are the places you’ll pay a premium for now, but book ahead for spring now and you’ll save.

Jimmy Im is a freelance travel writer based in NYC. He’s hosted programs on the Travel Channel and LOGO, and makes regular appearances on morning news shows as a "travel expert." He teaches travel writing courses and is also cofounder of

Photo credit: Winter cabin via Shutterstock

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