Vacation Home Rentals Blog

We’ve all had Martha Stewart envy.

A Hamptons vacation home landscaped with a garden of organic produce, fresh herbs to pepper our from-scratch meals with and a backyard big enough to host an elegant, yet intimate wedding reception. Heck, you’ve paid a mint for the same New York vacation rental for years–why not get in on the game now?

Mortgage rates are at all-time lows. Prices are plummeting. If you wait for them to sink further, will you be missing out on the pastoral paradise?

Perhaps.

Second-home ownership–or any home ownership–is not to be taken lightly. Heed the advice of a realtor who knows the market, and determine what style of vacation home suits your lifestyle, whether it’s a condo, cottage or mansion. Take factors like location, amenities and upkeep into account.  Think about hidden costs. Can you afford to maintain the property yourself or hire a management company to deal with tenant issues?

While that $8,000 first-time homebuyer tax credit doesn’t apply to purchasers who won’t be using the property as their primary residence, by all accounts, now is a good time to strike the MLS.

Landlords: Any more advice for consumers who seek to purchase a vacation home?

From State College, Pa., to Rochester, Minn., the cold has reared her frosty head. Winter has come early, and folks aren’t happy about it.

Well America, it looks like it’s going to be a long, blustery season, so it’s time to think about that warm weather vacation ahead. Counter seasonal affective disorder with thoughts of the other powdery stuff: the sandy, er, rocky beaches of California.

Now is as good a time as any to reserve your California vacation rental.

For you lucky Bostonites, flights on Virgin America are going for as little as $100 each way to Los Angeles if you purchase your ticket by Oct. 27. And why wouldn’t you want to? That white stuff during last week’s Patriots-Titans game wasn’t your TV on its way out–it was a blanket of snow, and the Pats’ earliest snow game on record, according to a FOXNews.com report.

Sure, it’s cool and pretty initially, but come January, when all the holiday lights are down and the roads are left a hard, slippery, grey, slushy mess, a weekend in California will be calling your name. Do it. Your UGG boots will need a rest.

It’s almost time to start making your list and checking it twice, and maybe start nixing the frivolous purchases of the past. (Does every relative require a Hallmark limited edition ormanent? Come on now.)

Besides, experience gifts are all the rage. Haven’t you heard? Presents that will have the recipient asking, “Why did I never do this before?” Like smelling a Colorado Aspen for the first time, and maybe even cutting down his first Christmas tree.

Or heck, why not skip the iPod stocking stuffers and go on vacation together? Let me count the reasons for spending the yule in a Colorado cabin rental.

1. Because cabins mean fireplaces, roasting marshmallows, wearing obnoxious snowmen and reindeer sweaters, and perhaps catching a glimpse of reindeer in real life.

2. Because you’ll likely be skiing, too. You’ll need to after the green bean casserole, sage sausage stuffing and fudge log cakes.

3. Because if you’re going to be stuck with your relatives–all 20 of them–it may as well be in an eight-bedroom house complete with a pool table, hot tub, bar and multiple flatscreens. Just think of all the joy you’ll have when battling over who gets the last Wii control.

4. Because it will most likely be a White Christmas. (Stranger things have happened, but I’d wager my third born that there will be snow somewhere in Colorado in December.)

5. Does a Christmas tree get any more beautiful when lit inside a log cabin?

Actually, lemme take that back, the California beach rental pictured perches over Monterey Bay, one of ForbesTraveler.com’s prettiest towns in the U.S. A total of 20 made the annual  list, including Union, Wash., Annapolis, Md., Sedona, Ariz., and Lake Placid, N.Y.

The feature sparkles with coastal communities, postcard-perfect Main Streets and desert diamonds. What strikes me the most about each of the selections is just how authentic the cities are: There is nothing chintzy or feels-like-a-souvenir shop about them.

Every city is its own distinct haven, a hometown for all to enjoy its hillside houses, charming downtowns, nature walks and breathtaking views of mountains, lakes and surf.

Monterey, a town rooted in the sardine canning industry, ran away with a ranking thanks to its rich marine history and award-winning aquarium. Cannery Row serves as a shopping, dining, lodging and nightlife hub for all who seek to be near the marine sanctuary and perhaps catch a glimpse of the sea lions at play.

What do you think? Are there any glaring omissions from the list? Let’s discuss on Twitter @checkincheckout.

This has to be a joke.

The Poconos house rental above lists for $1 million. That’s rent, people.

In the same posting, the owners of Lustgarten-On-The-Lake talk about how you can stay in their spacious Poconos Pine property for “peanuts,” which could mean just that. Will the landlords of this gem hit me on Twitter @checkincheckout? I’m impressed with your marketing tactic.

Because in a sea of listings, you still have to make your vacation home stand out.

Whether it’s a deck with sunset views, an outdoor kitchen next to a grotto pool or a location within the hottest neighborhood in San Francisco, you have to showcase your vacation rental just as aggressively as if it was listed for sale. Internet users are a savvy bunch who are willing to spend countless hours of “research” on the Web.

The Poconos house has a lot going for it already: a backyard lake with fishing rock, hot tub, fireplace, community pools and access to three ski areas nearby.

Would you pay $1 million for it? And if not, what would you pay?

Talk to me on Twitter.

Six winters in Chicago has definitely thickened my skin, but that doesn’t mean the sudden deep in temperatures doesn’t feel cruel and uncomfortable every time. Three weeks ago, I was wearing a denim mini-skirt. This week, I’m busting out the winter coat–and gloves.

A friend of mine, a victim of the recession who moved up from Florida, plans to head back home next weekend. No work in three months. Part of me felt sorry for her, the other thought, You lucky girl. Back to purple pink skies and 90-degrees and sunshine every day. How could that be so bad?

Collectively my city is moaning (and bracing itself) for what’s to come. A few of us, dreading that first attempt to shovel our cars from the snow, have pre-booked vacations to warmer climates starting in January to Virgin Islands vacation homes and Florida vacation rentals. The deals are out there, from last-minute deals to Tampa Bay to contemporary condos in South Beach.

Because regardless of where we live: We all know that sunkissed skin is like being on the receiving end of a warm hug from a long lost friend.

A drive through the New England countryside may be your fall ritual, but this year, why not shake things up a bit? After all, how many times have you seen brown leaves? (Every time you have to rake them, no doubt.)

Wander through Taos, N.M. and you’ll feel as if you walked into an Ansel Adams image.  The Sangre de Christo Mountains, Spanish for blood of Christ, stand majestically above this gorgeous city, where travelers plan getaways around hiking, biking and collecting art. In fact, the city reportedly tempts with more than 100 galleries just in case you’re looking for that perfect landscape painting to hang in your living room or turquoise pendant to wear with next summer’s peasant dress.

New Mexico vacation rentals are every bit as enchanting with their adobe-style construction. The one pictured, which rents for $1,200 a week through the end of the year, is a beauty with high ceilings, sizeable windows for mountain viewing and a kiva fireplace. Some homes bear the vigas(beams) common in many Indian villages.

So while this may not be Martha Stewart’s idea of a fall vacation, it could be yours.

Don’t forget the camera.

VacationHomeRentals.com is wealthy in choices for Seattle vacation rentals, but the contemporary cabin above had me at the deck.

The two-bedroom, two-bathroom chalet (just $1,000 a week through Dec. 31, 2010) isn’t too large or too small, and easily blends rustic charm (look at that woodwork and wall of windows in the living room) with modern trappings. Read: It’s the perfect vacation home for those who appreciate Mother Nature, but don’t care to pitch a tent for two weeks.

For travelers like me, that could mean taking a boat out on Lake Kachess, where we’d spend the day angling for trout, but returning to the lovely confines of a stainless steel kitchen to grill it.

A rougher I’m not.

You feel me?

My best friend’s husband has a dream: To own 40 acres on a rustic Montana ranch–complete with a John Deere, a babbling brook to skip rocks over and plenty of sticks for their sons to fence with.

Their current scenario forces them to live in a purgatory of sorts: Not the city, not the rural sprawl they so desire, but a Virginia subdivision complete with prefab, one-style-fits-all homes where the home owners association levies fees for discolored siding.

So to move away from the nosy neighbors is a respectable dream.

Big Sky Country, Mt., home to a ski resort of the same name, delivers some of the most fantastic scenery in the West, a peaceful area blessed with summits, trails, falls and log cabins with roomy porches. Big Sky vacation rentals inspire travelers to throw on a pair of Chap and a gallon hat and herd them doggies down the pasture.  OK, so maybe that’s an exaggeration, but beneath the wild blue yonder and at the foot of Lone Mountain, you’ll feel like anything is possible.

While 22-degree weather (the actual temperature today) is more winter than fall, if you’re game, the chilly weather is worth it for the endless picture taking opportunities. Tamarack and aspen trees pop in golds and yellows. Moose roam.

The scenes are enough to make you want your own, real life John Deere.

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.