The Art of Choosing the Perfect Stay

 One of the biggest factors in how your trip goes—whether it’s a weekend getaway or a year-long adventure—is where you stay. We just spent the last few weeks looking at accommodation options for seven weeks in Thailand, and there is a lot to consider even once you’ve decided which city to stay in. Your accommodation can shape your comfort level, your budget, your social life, ease of transportation, and how connected you feel to your destination.

Before we dig too deep into our accommodation options, we make a short list of non‑negotiables and nice‑to‑haves and make sure we’re on the same page. We have different lists of non‑negotiables and nice‑to‑haves depending on if it’s a short‑ or a long‑term stay. Having these priorities in mind makes it much easier to compare options and avoid decision fatigue, especially when you’re looking at accommodations for an entire year.

For us, short‑term and long‑term stays often call for very different types of accommodations.

Short‑Term Stays

For short‑term stays—anything from one to five nights—we typically prioritize convenience. Hotels tend to shine here, offering easy check‑in, daily housekeeping, and on‑site amenities like shuttles, activities, breakfast, and can be very close to airports for easier travel days. For quick trips, these features can save time and reduce stress.

We usually pick rooms with two queen beds, which are widely available, and we try and look for access to a pool and food within walking distance. Our kids also tend to up before the sun and have no volume filter or awareness of how much they’re stomping and jumping around. Due to that, we often book a first‑floor room, so guests under us don’t have to suffer through 5 a.m. noise.

Airbnb’s are doable for short term stays and we have done quite a few, especially when traveling as a larger group. The thing to keep in mind is they tend to include a cleaning fee that can be hundreds of dollars on top of the nightly rate. It’s typically the same cleaning fee whether you’re staying there for two nights or two months so for short duration stays it can make Airbnb’s less economical. 

 Long‑Term Stays

For longer‑term stays, we want something that feels more like home. We look for amenities such as a kitchen, laundry facilities, two bedrooms and separate beds for the kids so we can spread out a bit and get our own space.

We primarily use Airbnb (and VRBO to a lesser extent) to find apartments, condos, or houses to rent. These options make it easier to settle into a routine and can save us a lot of money on dining out. We still like to find a place with a pool—nothing beats it for easy entertainment for the kids and as a break from hot days of exploring.

For our sabbatical, our long‑term stays will be more about relaxing, slowing down, and using the space like a home while we establish a routine. So for these longer stays, location and quality become even more important. If a place is dirty, noisy, poorly maintained, or in a bad part of town, you could be stuck there for weeks. That makes thorough research essential.

Another useful tip: there can be significant savings when booking accommodations for a month or longer. While researching places in Thailand, we found listings with 30% discounts for monthly stays—making it cheaper to stay for 30 days than for 21. Because of this, we always play around with dates and durations to see if there are opportunities for savings.

 The Importance of Reviews

Reviews are one of the most powerful tools travelers have, but they require careful reading. A high star rating is helpful, but the real value is in the details.

We look for patterns rather than isolated complaints. One negative review about noise may not be a dealbreaker, but repeated mentions of cleanliness issues or poor communication should raise red flags. We pay close attention to reviews that mention:

  • Accuracy of the listing or room description
  • Cleanliness and maintenance
  • Host or staff responsiveness
  • Noise levels and neighborhood atmosphere

Also, we make sure to check the dates of reviews. More recent feedback is usually more relevant, especially for properties where management or condition can change over time.

One thing we watch for is places with a mix of very poor reviews and glowing, overly generic ones. In some cases, those positive reviews may be manufactured by friends or family of the host to offset legitimate negative feedback from real guests. Additionally, we always verify house rules, check‑in procedures, and cancellation policies. Communication with the host is key—responsiveness before booking is often a good indicator of how your stay will go.

For our sabbatical, we’re prioritizing places with strong cancellation policies. Even with careful planning, things can go sideways quickly, and having flexible accommodations could make a big difference if they do.

Finding the perfect place to stay from halfway around the world isn’t easy—and honestly, it’s not always possible. Sometimes you find a great layout in a less-than-ideal location, or a place with glowing reviews that just doesn’t quite fit your needs. Sorting through all the options and trying to piece together the best mix from your lists can be frustrating, but starting early and putting in the effort really can pay off. We’ll be sharing what worked well for us (and what didn’t) as we go, and here’s hoping there are more wins than misses along the way.