Vacation Home Rentals Blog

The Obamas–Bo included–will be vacationing in a Martha’s Vineyard rental at the end of August. The 28-acre farm rents for $50,000 a week and sports a pool, beach, underground movie theater, golf practice tee and–good thing for Barack–a basketball court.

Am just a wee bit jealous, but aren’t we all?

The president made a good point, though. Just because these are trying times for Americans doesn’t mean he shouldn’t take out quality time to spend with his daughters. In fact, we should all be doing that if we can–slowing down, getting back to each other–and it doesn’t have to involve a $20-million estate.

My vote goes to New York vacation rentals in the Adirondacks. A dip in the database surfaced this  Chateaugay Lake vacation home, which sits right on the water and spoils guests with glimpses of eagles, heron, osprey and moose, lists for a manageable $650 a week through the end of September.

In quiet moments, you’ll sizzle steaks on the grill, drink beer on the deck or fish. Hate sitting down? Get your heart rate going while kayaking or hiking one of the many trails nearby. Another plus: For an additional fee, you’ll be able to take your own pooch on vacation, too.

Just like the Obamas.

See, you’re more like them after all.

No disrepect to my Indiana neighbors, but this Chicagoan, if she had the choice, would be a native Wisconsinite.

Maybe that’s because every since I met my Door County colleague, I’ve secretly wanted to shoot skeet, eat cheese curds, dance polka and down Wisconsin-brewed beers while watching a Badgers game. It’s the kind of pride that refuses to be hidden–just like her accent.

For now, I’d settle for a Wisconsin vacation rental like this Lake Geneva vacation home. It’s a one-tank trip from Chicago (there and back), and easy on the bank account. The Red Cottage rents for $1,200 a week, and is close to Lake Geneva proper, a town brimming with charm, from antique shops to lakefront mansions.

Naturally, the town revolves around the lake so if you like water skiing, boating or fishing, you’ll feel right at home. And if you don’t, well, wander along the 20.6-mile lakeshore trail or catch a ragtime band by the shore (which happens to be this weekend) or sail above the waters on a chartered balloon.

You won’t want to come back down.

Tell us @ checkincheckout on Twitter: What’s the best vacation destination from your hometown for a one-tank trip?

“If there is a heaven on earth, I think I was there today,” wrote a friend on her Facebook status of her stay in St. John, Virgin Islands.

Such cooing has been a daily, sometimes twice-a-day, habit of the girl since she moved to the VI two weeks ago. If I wasn’t writing about paradises all the time, I would probably want to smash her mobile phone’s camera into a thousand little pieces. But today’s update was kinda nice–none of the “Gina is island bound in 10 days” business. It actually had soul. It sounds like her surroundings truly moved her.

Lucky girl.

A Caribbean house rental still ranks No. 1 on my list of vacation destinations. The ease of access (no passport necessary), affordable airfares (I found a trip for $492 roundtrip for next week on Delta.), U.S.  dollar currency and airy, cliffside homes would suit my getaway needs down to a tee.

Homes like the one pictured are commonplace in the VI, decked out with sprawling verandas, open fire pits, wet bars and outdoor/indoor living rooms to enjoy the sea breezes. You, the surf and the sunset. What could be better than that?

I’ll tell you what: Actually being there.

Tell my friend Gina I said hello.

You’ve done Disney at least 10 times, and it’s not the season for snowboarding. Your teens–or tweens–are a hard-to-impress bunch and used to a certain level of stimulation. Remember: This is the generation growing up with the words iPod Touch and Wii in its lexicon.

This year, wow them with a vacation to Tinseltown.

After all, what’s cooler than Hollywood?

From Studio City rentals like the one pictured to Santa Monica beach houses, California vacation rentals strut with style. While in La La Land, you could try to …

Attend a TV show taping
Walk along Robertson Boulevard to stalk celebrities
Have your picture taken by your fave it-girl’s star on the Hollywood Walk of Fame
Taste fro-yo from Pinkberry
Tour studios
Hike up to the Hollywood sign

And most important: Pick up cool back-to-school tees at Ed Hardy

The kids will be the envy of all of their friends and get to say they went to L.A. instead of Concord, Vt. No offense to Vermont of course.

Come the last week of August, the Obamas will be rounding out their summer in a Martha’s Vineyard vacation home, according to an interview with CBS News anchor Katie Couric.

Just where he’ll stay is another story, but if Plan A falls through (whatever that might be), we’ve got a cute “Little House in the Big Meadow,” the nickname coined by the owner for this two-bedroom, two-bathroom Martha’s Vineyard rental. The home is set on three acres hidden after a mile’s drive down a dirt road, the perfect setting for presidential discretion.

There, he, Michelle and the kids could play Clue in the sun-drenched living room, make lasagna in the kitchen, then take a dip in the solar-powered pool. (Yes, double brownie points for the “green” energy source, a key component of Obama’s campaign.)

The haven, made even more picturesque by the visiting deer and Harrier Hawk, is centrally located next to all six towns and beaches, yet away from the summer crowds.

Because even the First Family need a little privacy sometimes.

Perched in a cloak of trees away from eavesdropping, judgmental strangers, this Washington vacation rental is exactly the kind of place Edward Cullen and Bella might call their love nest.

It has that Twilight feel, doesn’t it? An air of seclusion.

The one-bedroom cottage is priced a mere $99 a night, one of many last minute vacation rentals on our site. And while it’s not the modern chalet that the Cullen family has decked out with expensive art and designer furniture, it’s not shabby either. Check out the cathedral windows and deck.

You could have your morning coffee out there, grill steaks or read the latest installment of the popular Stephenie Meyer’s series.

Or you could do what two humans do while alone in the woods. Hint: It has nothing to do with singing campfire songs.

A year and 218 posts ago, I promised to spill vacationhomerental.com’s secrets on the best travel deals, from Florida vacation homes to Hawaii vacation rentals and everywhere in between–and beyond.

We’ve been to Oregon, the Philippines, Thailand and Maine. We’ve talked log cabins in Wisconsin, ski chalets in Colorado, thatched cottages in Ireland and ooh-la-la flats in Paris. Every single property–even the budget ones–has stirred wanderlust in me, and perhaps in you, too.

And while it’s been a trying year in so many ways for the nation, the urge to dive off a cliff in Greece and play flag football on a lawn in New England hasn’t waned. To want to be on vacation is only human.

I know, I know: If I only had the money. If I only had the time.

Well hopefully the blog has helped you make it happen with last-minute deals and value-priced condos and estates. I look forward to surfacing more.

Loyal readers and newbies to the site, is there anything you’d like to see more on Check In, Check Out? Hit me on Twitter @ checkincheckout. And thanks for celebrating today with us.

Let’s go find another pearly white beach to twinkle our toes in.

This beauty, one of many tempting Hawaii vacation rentals on our site, goes on my bucket list.

Blame it on my mama, but I tend to look at the cost first before even pondering any purchase. Why flirt with hurt if you can’t afford it? But with the way fares are going, come next August, I might be able to swing this trip to this Big Island two-bedroom, two-bath condo for just $899 a week.

The property owner describes the setting as 1880s Hawaiian village complete with lush landscaping, multiple barbecue grills to host your own luau and thatched huts. The kids won’t be bored–like they could be in this tropical oasis–with all the extracurriculars like lei and jewelry making, canoe crafting, plus a sarong demonstration to properly tie one for yourself. Because a tropical outfit isn’t complete without an orchid in your hair and a bright-colored sarong.

On Aloha Tuesdays, the host offers complimentary PUPUS (snacks), live entertainment and hula lessons. The units have indoor kitchens and are conveniently located near a grocery store and Walmart just in case Junior runs out of Pull-Ups.

Now, let’s just pray that the fares continue their downward trend. I can hear the ukuleles now …

I’m in a Kennedy frame of mind, what, with JFK Jr. having passed 10 years ago today. The beloved Prince of Camelot met his fate when he crashed his plane–with his wife and sister-in-law in it–off Martha’s Vineyard.

The Cape Cod locals continue to memorialize his life and his father’s. At the John F. Kennedy Hyannis Museum, some 20 million visitors toured exhibits featuring more than 80 photographs depicting the famous family’s ties to Cape Cod from 1934 to 1963, according to the Cape Cod Times.  As much as they were American royalty, they were part of the Cape Cod community.

And no doubt: The mystique of the Kennedys builds the appeal of the Cape as a desirable vacation destination.

If you’re a history buff, why wouldn’t you want to tour the playgrounds of John-John and family and stay in a Cape Cod house rental? The home above affords peace, quiet with its wraparound porch, large guestroom and access to woodlands, bike trails and a private residents’ beach.

You don’t have to be a Kennedy to appreciate all that.

Let me qualify: All vacation home owners are hot for renters, but apparently the owners of Wisconsin vacation home rentals and Michigan vacation rentals are having an especially challenging time selling those homes, according to Crain’s Chicago Business. What that could mean for you: Great deals on getaways.

And in a twist of irony, folks are turning to the bustling Midwest metropolis–Chicago–to purchase their second homes, The New York Times reports.

A vast supply of condos priced just right plus a cultural explosion in the Windy City equals buyers.

Makes sense. But personally–and take this with a grain of sand because I’m a Chicagoan–I’d rather be spending my vacation in a log cabin or on a crescent-shaped beach in Hawaii.

But heck, I’d take Wisconsin any day.