Hitting the Road: Where to Stay?

One of my favorite things to do – outside of actual travel – is travel planning. Everything about it is fun to me: searching for flights, planning routes, and finding a good place to stay. I even love planning trips for friends and family (hit me up if you’re interested!).

One of the more labor intensive parts of planning a trip is deciding where to stay, and the choice is very personal. Many travelers prefer the convenience of a hotel with its daily maid and room service, and other concierge-type conveniences, however, Dave and I are fans of vacation rentals if we’re staying longer than two nights. Often with a vacation rental, you get a lot more space for about the same cost of a hotel. The downside to vacation rentals is there is less certainty with what you’ll get, and the check-in process is not always as easy as a hotel, particularly if you are arriving late at night. My experience is that with a vacation rental you frequently get a more personalized experience with your host.

After many hits and a few misses, I’ve developed a good process for picking winners when it comes to vacation rentals.

When searching for rentals across multiple platforms, I see all the same listings. At the end of the day, the platform can make the difference in your experience. I prefer Airbnb for a couple reasons, but the main reason is that Airbnb posts automatic “reviews” on the guests’ behalf if the host cancels the reservation. This alerts potential guests if the host has a history of cancelling, which could be a major trip downer if your reservation is canceled days before your arrival, leaving you scrambling for new accommodations. VRBO doesn’t do this. Airbnb also shows the total rental price, with fees etc. Don’t be surprised to see two listings at $100/night but vastly different total rental price. Sometimes a more expensive nightly rental is cheaper over the length of stay because of lower service fees and cleaning charges.

Another reason I like Airbnb is that they don’t allow hotels to advertise on their site (VRBO does), and I’ve found Airbnb hosts are more responsive, and their calendars more up to date. Regardless of the site you use, below are my tips for finding the perfect vacation rental:

  1. Finding the right location for your accommodation is the first and most important criteria. Dave and I like to stay in the center of town within easy walking distance to attractions, transportation and restaurants. I’m also partial to “Old Towns” with cobblestone pedestrian streets and architecture, so I always start my search by locating the historic district of my destination. I then search the area for restaurants – wherever there is a good cluster is usually where I focus. You should also consider parking options if you’ll have a car, and transportation options to attractions (are you able to walk or take public transportation, or a taxi? How far is the walk to public transportation?).
  2. Once you’ve narrowed down your neighborhood(s) and created the criteria for your search (budget, number of beds, bathrooms, washer/dryer, etc.), you’ll want to pay very close attention to the pictures in the listings. There are deal-breakers for me, but you may have different expectations and criteria. My deal-breakers:
    • Dark rooms lacking natural light. Even if the rooms are well-lit with lamps, etc. if you don’t see windows, you could be renting a basement apartment that might be damp or stuffy.
    • Listings that don’t show every room and every bed. Be aware of pictures that show what appear to be the same room with different bedding, making the rooms look different. Look for pictures on the walls, the placement of windows, etc. to ensure you’re actually looking at every bedroom. If a listing describes two bedrooms but only shows one, I will avoid that property.
    • Dingy or worn bedding. I want assurance that the bedding is high quality and clean. If the bed is rumpled or the linens look cheap or faded, I pass.
    • Same goes for the furniture – a beat up sofa or one that’s covered in an ill fitting sofa cover or blanket is a turn off and might indicate a dirty apartment.
    • Listings that don’t show the bathroom, or specifically, don’t show the shower. If you don’t see the shower, don’t rent. We’ve ended up in places with bathtubs and a handheld shower nozzle which is not ideal. We had one apartment that didn’t have a shower curtain, which we ended up buying for the duration of our stay.
    • Personal items in the bathroom and around the apartment. If there is a toothbrush, personal grooming items in the photos, or a lot of personal clutter, I steer clear.
  3. Read the reviews. If there are no reviews, or no recent reviews, I skip the property no matter how nice it looks (the exception is if there are no other decent options I might take a chance on a unit without a review for a short stay). Pay attention to reviews about noise, cleanliness, the check-in and communication process with the host, the comfort of the beds, odors, non-working appliances, etc. If there is an unfavorable review that was posted years ago, and all reviews since have been good, I will assume the issue was rectified and consider the property. But if you see a theme, you may want to move on. We rented a lovely apartment in Dubrovnik, but I didn’t pay attention to the reviews, much to my group’s detriment. The apartment was above a VERY loud nightclub, and we were assaulted with loud club music and bottles rolling down the stone steps every night until 2:00 AM. For a week. Needless to say, after that experience, I now pay close attention to reviews!
  4. Before you book, establish communication with the host to clearly understand the location of the rental (are there a lot of steps, is there a lift/elevator, is there parking, etc..) but don’t drive the host crazy with questions. As the owner of a vacation rental property, I’m wary of renters who ask a lot of questions because they tend to be difficult guests. You’re probably not a difficult guest so don’t send any signals to the contrary before you’ve even decided on your rental.
  5. Pay attention to the cancellation policy before you book. I try to select properties that allow a full refund if cancelling within 7 to 30 days of arrival. Even after I’ve booked, I continue to search for new rentals that might be more appealing, and it’s good to have the option to switch without a penalty.

My last suggestion is to never, ever, select a vacation rental from Craigslist or any other classified service, and beware of hosts who want you to send them money via wire transfer vs. the payment system on the site, which is secure and provides protection should something go wrong with your rental.

I hope this helps in your travel planning…. Please feel free to ask questions or submit your own tips in the comments section.

Until next time!




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