What You Need to Know About Holiday Rental Houses

NEW YORK (MainStreet) — Many families might still go over the river and through the woods to grandma’s house for the holidays, but as more and more families become transient and grandma and grandpa decide to downsize for a more carefree lifestyle, more families are opting to rent large vacation homes, condos and cabins for their holiday gatherings.

Sharing a vacation rental with extended family has its perks, but if you don’t prepare you might experience a holiday fiasco.

T.J. Mahony, co-founder and CEO of FlipKey, a service based in Boston that lists more than 170,000 rental homes around the world, says the first thing you need to do for your Thanksgiving is choose a place to go and a home, condo or resort cabin to rent. Mahony says not to get anxious and think there aren’t any rentals left for this year. “Lake Tahoe, for example, is very popular, but it has a tremendous amount of inventory,” Mahony says. (Typically you need only four to six weeks to book.) “Just remember that the larger the space you need, the smaller the inventory choices.”

Chuck McCarter, general manager and managing partner for Oak Haven Resort and Spa in Sevierville, Tenn., says they have 22 rentals of 3,000 to 4,000 square feet, but those book one to two years in advance. “Thanksgiving is definitely our most popular time,” McCarty says. “Christmas doesn’t book up as early.”

Even if your pick is already booked, Mahony says not to despair. “If your first pick is rented, ask the owner or manager if they have other recommendations, they can be a tremendous resource for you,” Mahony says.

Once you’ve found the place you want to stay, it is time to discuss the particulars with family members. McCarter says that while his resort, as well as many others, separate bills, the easiest thing to do is to have one or two family members put the charges on their card and collect the money from among the relatives.

“Most of the time it is one or two ladies, such as sisters, who organize the event,” McCarty says. “They will usually even make a list of which cabins what family members will take and we can put those into our computer and have it all ready for them.

Once the property is booked and rooms are assigned and paid for, it comes down to telling people what they should bring. “The overall success of the trip can sometimes be defined in the first two hours,” Mahony says. “If you get to your destination and it doesn’t have toilet paper, paper towels or shampoo, then someone is going to have to leave again to pick those items up.”

Most properties have full-service kitchens. McCarter says the holidays are so important for his business that they conduct full inventory checks before the holidays to ensure families have everything they need to prepare a full holiday meal.

Some resorts, such as Big Cedar Lodge in Ridgedale, Mo., a resort near Branson with lodge-style rooms and cabins, will even provide catered meals and come back to clean up afterward.

Decorations are a big consideration for families as well. Big Cedar and Oak Haven decorate their cabins for Christmas, and Big Cedar has a large Christmas tree adorning its main lodge area. For a fee, managers will dispatch elves to the cabins to read to children and send Santa to deliver gifts on Christmas morning.

If you’re renting a home, it may or may not come decorated. That’s something you should discuss with the owner or manager, Mahony says.

Some people are going to a location for more than quality cabin time with the extended family. If you’re booking a holiday rental for the skiing, ice fishing or other outdoor activities, you might put someone in the family in charge of finding out what else is available to do in the area, Mahony says.

The average booking for a holiday or winter rental is 6.5 nights. “Very few people can ski for six days straight,” Mahony says. “Ask the manager or owner about other activities in the area and plan on doing those activities too.”

Sydney Friar, PR manager for Big Cedar, says people should remember to bring casual wear for those outdoor activities. “Outdoor activities are a great way to connect with family, and we have a lot of activities during the holidays,” Friar says.

The most important thing, McCarter says, is to choose a resort or rental that is accommodating to your needs and has customer service people who will listen. “That’s why we don’t take online reservations – we want to speak to our customers so we understand what they’re looking for,” McCarter says. “Any good resort will have people who don’t mind speaking to you and answering your questions.”

Other tips from McCarter:

  • Make sure to tell the resort if you have aging or ill relatives coming. Cabins in mountainous terrain may have steep walkways or driveways or multifloor plans that may not be appropriate.
  • It’s always a good idea to check the local medical facilities and their locations just in case.
  • McCarter recommends that families leave expensive electronic gadgets and jewelry at home. “We have found everything imaginable left in the cabins,” McCarter says. “We even once located a $10,000 ring someone had taken off to cook. You’re in a strange place and away from your usual routines, it’s easy to lose or leave items.”
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