Vacation Home Rentals Blog

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Friday is the grand reveal for the host city of the 2016 Summer Olympics, and to call it early, I’m going to say Chicago.

Disclaimer: The author of Check-In, Check-Out is a full-time, almost decade-long resident of the Windy City, and damn proud of it.

Why wouldn’t I want to show off my adopted hometown?

While the games are years off, it’s a sure bet that Chicago vacation rentals will play a big part of housing. In fact, I predict a rush on Chicago vacation condos suddenly populating this site and others, thanks to folks seeking their piece of the rings. Travelers shouldn’t be discouraged if they don’t land a room downtown–our neighborhoods along the glorious Lake Michigan coastline are our best-kept secrets, brimming with any kind of ethnic food you could ever want, legendary sports teams and funky shops.

Wrigleyville. Edgewater. Hyde Park.

Ever heard of it? It’s a certain president’s former zip code.

And he’ll be in Copenhagen to lead the charge. Here’s hoping for gold tomorrow.

It doesn’t surprise me one bit that this week the terms “Chicago vacation rentals” came up high in search results. The city pumped its collective fist since the mercury broke 80 degrees, which wasn’t that long ago. We have a lot of partying to catch up on.

Earlier this month, I saw folks in outerwear. (Trench coats and the like, but it was too chilly to bust out the sundresses.)

But the weather heated up just in time for Grant Park–home to that other ginormous celebration in August, Lollapalooza–to host the Taste of Chicago (June 26-July 5), an annual buffet of the city’s best eats, from giant turkey legs to Eli’s Cheesecake.

Tourists will be struck by how clean Chi-Town is, how friendly its people are and how good it feels here in the summertime. Chicago in June is like that first beer you crack open at a ballgame or the first time you fire up that grill. You can’t be help but smile. After surviving subzero temps, we “earn” the chance to lay out at Oak Street Beach, drink alfresco at numerous neighborhood festivals, have mimosas on the patio of the Kerryman and ride our bikes down to Promontory Point. We suggest you out-of-towners do, too, and quick.

Who knows how long these balmy days will last?

So hurry up and find your vacation home already.

A public shout-out to the first reader to name the ferris wheel above. And no cheating. (Here’s a hint: Drew Barrymore filmed a key scene in “Never Been Kissed” there.)

Ding-ding! Chicago’s Navy Pier.

On a clear, summer day, there’s nothing more perfect than admiring the city’s skyline from the Ferris wheel car. To the west, the curvaceous, sleek Lake Point Tower, to the north, the John Hancock and that windy boulevard we Chicagoans heart: Lake Shore Drive. If you happen to be lucky enough to be staying in a Chicago vacation rental downtown, you may even spot it during your spin. (Another thing to do while buzzed at the Signature Lounge on the 96th floor of the Hancock. Go at night to eyeball the skyscrapers and city blocks that twinkle on the massive, maze-like horizon.)

Ferris wheels bring out the cheesy tourist in all of us, the feeling that you’re 10 again. They’re romantic, too. Just you, your sweetheart and the open air.

I’ll skip the blatant “top of the world” cliche, but you get my drift.

What other cities host these timeless, family-friendly beauties? Book a Santa Monica vacation home, Dallas vacation rental or Anaheim vacation home to find out.

As a parent, I’ve learned many things. Among them: 1) Bring a change of clothes. You never know when the bladder (or stomach) will fail. 2)Nothing makes a kid happier than Chuck E. Cheese. 3)When Chuck E. Cheese isn’t nearby, the promise of an amusement park works, too.

Count the Wisconsin Dells–the so-called water park capital of the universe–on the list of tot-approved distractions.

I’d never heard of the Dells until I moved to Chicago seven years ago, and since then, friends haven’t stopped raving about it. “I couldn’t get my son to leave the indoor water parks,” one pal said, while another couldn’t get over the fact that “it feels like you’re stepping back to the 50s” with its numerous lodge accommodations and deluge of families.

Combined with affordable Wisconsin Dells vacation rentals, the getaway should be more than on my radar. It should be this year’s summer vacation. The two-bedroom, one-bath cottage above is just $349-$699 a week, depending on the time of year.

The Dells counts more than 20 indoor and outdoor water parks in its repertoire, plus golf and ski options and the nearby Wollersheim Winery for mom and dad.

Hey, nobody said you have to play all day in the pool.

I definitely risk bodily harm by making the following statement: Last baseball season, one set of fans showed just as much heart as those in my adopted hometown of Chicago: The Tampa Bay Rays’. But I’ll have to give it to ‘em, the Rays made a go in 2008, and it was refreshing to see the youngins reach the playoffs–despite the fact that some of the food at Tropicana Field leaves much to be desired. (Bloomin’ Onions, really?)

Because baseball is so personal and to reduce my exposure to any more fallout, I limited these picks to three. That, and because I’m not all that into sports. Now the people watching and hot dogs and beer I love.

Here are my pitches in no particular order.

1. Tampa Bay
It is spring in Florida, which means some of the best weather in Tampa Bay. 80s during the day, 60s at night. Who could argue with that? Plus, from a St. Petersburg vacation home, you can watch the sun set into the purply pink horizon. Baseball in true warm weather is great, but being able to dip your toes into the pool afterward is heaven.

2. San Francisco
Boston may have its Green Monster, but AT&T Park won the 2008 Sports Facility of the Year by Sports Business Journal and Sports Business Daily. Makes sense. The home of the Giants spoils fans with views of the Bay Bridge. Just lovely.

3. New York
It’s easy and cliche to hate on the Yankees, but this year marks the momentous opening of a new stadium on April 16. (Not to leave you Mets’ fans out either. I know you’re also getting a fantastic park on April 17.) Either way, a trip to New York is not time wasted, especially if you have spring wardrobe shopping to do. Park yourself in a Manhattan vacation rental, then drop dad off at the game so you can focus on your favorite pasttime: scooping up new labels. Think of it as your own fantasy league, trading old labels for newer, more expensive ones for a look that wins.

Let’s play ball!

It’s OK. We wanted to be there, too.

While you may not see history in the making when Barack Obama gets sworn in as the 44th president of the United States, you can experience Chicago, the loveable metropolis he just left. Stay in this vacation condo to still be downtown but not pay downtown prices or any one of the many Chicago vacation homes available on our site.

The 45th-floor apartment is close to Grant Park, where Obama gave hundreds of thousands of people in this city a lump in their throats when he emerged victorious on Nov. 4. When you’re done getting a photo of that famous venue, hop in a cab to Manny’s, one of his old haunts, or if you like fine dining, Blackbird, for stylized eats.

At the end of the nights, sit by the floor-to-ceiling windows to enjoy the twinkling skyline that makes Chicago a world-class destination.

But we’re biased.

We live here.

And so did Obama.

America, you have a huge decision to make tomorrow. Think of it this way, politics aside, who would be more fun to rent a vacation home with: McCain or Obama?

And the bigger question: Which candidate’s state would make the best getaway: Alaska, Arizona, Delaware or Illinois?

Let’s take a straw poll using properties listed on VacationHomeRentals.com. These are in no particular order, but since Sen. Joe Biden’s home state of Delaware has never been featured on the blog, we’ll start there.

Delaware vacation home
During this campaign, Biden has been painted as a man who never forgot his modest roots. Well then he would certainly appreciate this purpose-built condo on Bethany Beach. The fifth-floor unit is steps from the pool and the Atlantic with patio chairs on a 25-foot balcony. There, you and Joe the Senator could swap ideas on clean coal technology and health care reform.

Alaska vacation rental
Gov. Sarah Palin would feel right at home at this log chalet thanks to luxe touches like a spa tub with glass mosaic tile, standup shower, gorgeous bedding and furniture. Maybe you and she could chat over hot cocoa by the fire about how she went toe-to-toe with the oil companies and prevailed, and also if she ever braved nearby Mt. McKinley herself.

Chicago vacation condo
The Obamas are city cats for sure, dining at foodie staples like Aigre Doux, Blackbird and Schwa. We’d bet Barack and Michelle would love this 23rd-floor penthouse suite for the very reasons all Chicagoans heart their city: Views of the skyline and access to world-class dining, nightlife and more.

Sedona vacation home
Sen. John McCain owns a home in the Sedona area, where this charming pueblo, which is located in an area of custom horse properties, hosts guests looking for a little bit of Southwestern flair. It mimics the style with Spanish-influenced furnishings, arched doorways and alcoves and 10-foot ceilings. John is reportedly a grill master so you could put him to work on those cowboy steaks.

And while you’re at it, ask him how he’ll bail us out of this crisis, will you?

The carol “Silver Bells” surely must have been referring to Chicago–no offense Manhattan–in its lyric, “It’s Christmastime in the city.”

No big city does it better when it comes to holiday style.

And I’d like to see the economic slowdown as a plus for hardcore shoppers to take advantage of all the deals on the Magnificent Mile, what has to be the most sparkly, elegant thoroughfare during the season in the U.S. While the street is mostly mainstream stores that you would find in other American cities–everything from Saks to Eddie Bauer–its beauty is unmatched.

This Chicago vacation condo is within walking distance from Michigan Avenue, Navy Pier, Millenium Park and a free trolley that takes tourists to all the downtown landmarks.

This two-bedroom, two-bath vacation rental peeps out to the lake and the architechural gems that make the Second City an incredible getaway year-round.

Not what you’re looking for? Check out other Chicago vacation rentals for your holiday spree.

We’re in that window of the year where if you’re not paying attention, you could blink and miss those leaves turning from green to gorgeous hues of amber, gold and brown. Before it’s too late, isn’t a road trip in order to catch Mother Nature go from green to redhead?

1. Washington, D.C. vacation rentals
This million-dollar Washington, D.C. vacation home is emblematic of our nation’s capital’s elegance and history. The four-bedroom, two-bath Queen Anne sits on Capitol Hill and is only two blocks from the Metro. Take a long weekend through the neighborhood to soak in the irresistible fall foliage, landmarks like the U.S. Supreme Court and the Smithsonian, then retire the covered porches to enjoy the flower garden.

2. Williamsburg vacation rentals
A little further south, find the town that will always mean fall to me, from field trips with my seventh grade class to Jamestown to outlet shopping and sightseeing in Colonial Williamsburg. Tree-lined streets and 18th-century architecture abound, guaranteeing that memory card will be loaded with photos from your stroll into our country’s past. Can’t afford that $400-a-night B&B? Try this vacation condo, reasonably priced at $89 a night.

3. Colorado vacation rentals
Colorado’s vast mountain ranges, sparkling lakes, diverse wildlife and rustic lodges would tempt any Floridian or other resident on mostly flat land to consider relocation. These Divide vacation cabins offer prime access to leaf watching, where the Aspens deepen to shades of gold.

4. Maine vacation rentals
The road up to this Belgrade Lakes vacation cabin is hugged by woods and ends next to a placid lake. Get there before the end of September to enjoy that one last meal alfresco or kayaking outing, and don’t forget to tote the camera to snap images of all those beautiful New England leaves.

5. Missouri vacation rentals
What a picturesque Midwest escape. This turn-of-the-century stone house near Branson, anchored on 35 acres surrounded by trees, boasts a yard for that impromptu game of touch football and a firepit for roasting marshmallows. Did we mention the hiking trails? It doesn’t get any more autumn than that.

I have a few friends who went away to their Michigan or Wisconsin vacation homes this weekend, or shall I say, vacation homes their parents own. I’m in love with the romance of that–vacationing at the same lake house every summer–and frankly, I’m also a little bit jealous.

Once again, Crain’s Chicago Business validated the story that’s become all too common in 2008: People are staying closer to home and taking shorter vacations to curb costs and protect their job security.

As a result, Harbor County, Michigan vacation homes like this one have enjoyed a boom in bookings this summer, and I’d bet they could continue during fall, winter and spring if property owners play their cards right.

Whether it’s a huge backyard for kids (and adults) to throw the ball around, a gourmet kitchen for cooking up that anniversary dinner or a stone fireplace to huddle around when temps do a freefall, your homes’ best assets should be showcased on your listings. It might even be worth it to adjust your photos and property amenities according to the season to promote your home during the off season.

Because now that the economy is hurting, would-be renters will be looking for reasons to justify giving up those hard-earned dollars.