How to Choose Where to Stay
Where you stay can completely change how a trip feels.
You can book a beautiful hotel, but if it’s far from everything you actually want to do, you may spend half the trip in traffic.
You can also save money on a cheaper stay and then spend the difference on Ubers, trains, or rental cars just trying to get around.
For me, choosing where to stay is less about finding the “best hotel” and more about finding the right base for the trip.
Start With the Neighborhood
Before I even start comparing hotels, I look at the neighborhood.
I want to know:
What the area is like during the day
What it feels like at night
How walkable it is
What restaurants and cafés are nearby
How close it is to the things I actually want to do
What transportation looks like
Whether I would feel comfortable getting back there late
A great property in the wrong neighborhood is still the wrong stay.
Map Out What You Actually Want to Do
This is one of the easiest ways to narrow things down.
I look at the places I already know I want to visit and see where they cluster.
If most of my itinerary is happening on one side of the city, I probably do not want to stay 45 minutes away just because the hotel is cheaper.
For me, convenience has value.
Especially on shorter trips.
Think About the Type of Trip You’re Taking
Where I stay depends heavily on the trip.
A weekend city trip is different from a beach vacation.
A birthday trip with friends is different from a solo trip.
A work trip is different from somewhere I plan to barely leave the resort.
I ask myself:
Am I going to be out exploring all day?
Do I want nightlife nearby?
Is this a relaxing trip?
Am I renting a car?
Will I be using public transportation?
Do I care about being near the airport?
Am I planning to spend significant time at the property?
The answers usually make the location decision much easier.
Decide What You Actually Need From the Stay
Not every trip needs the same kind of property.
Sometimes I care about:
A really good gym
A pool
A great view
A balcony
A kitchen
Laundry
A desk for work
Free breakfast
Parking
A lounge
A strong restaurant or bar
A nice lobby or common space
Enough room for a group
Other times I just need somewhere clean, comfortable, and well located because I know I’ll barely be there.
I try not to pay for amenities I’m not actually going to use.
Hotel vs. Airbnb vs. Resort
There is no one answer here.
It depends on the trip.
Hotel
I usually lean hotel when I want:
Daily housekeeping
Front desk support
Amenities
Easier check-in
Security
Loyalty benefits
A more consistent experience
Hotels also make sense to me for short city trips where convenience matters.
Airbnb or Vacation Rental
I’m more likely to consider a rental when:
I’m traveling with a group
I want multiple bedrooms
I need a kitchen
I want laundry
I’m staying longer
The group wants shared living space
But I always compare the full cost because cleaning fees, service fees, and other charges can change the value quickly.
Resort
A resort makes the most sense when the property itself is a big part of the trip.
If I’m planning to spend most of the time at the pool, beach, spa, restaurants, or property activities, I care much more about the resort experience than being in the middle of a city.
Look at the Total Cost, Not Just the Nightly Rate
A $180 hotel is not necessarily cheaper than a $220 hotel.
The cheaper hotel might have:
Resort fees
Parking charges
Expensive transportation
No breakfast
No airport shuttle
Extra fees for amenities
Meanwhile, the more expensive hotel might include things I was going to pay for anyway.
I compare the actual trip cost, not just the number that appears first in search results.
Read the Recent Reviews
I care much more about recent reviews than a glowing review from four years ago.
I look for patterns.
If one person says the room was noisy, that may be a one-off.
If 30 people mention:
Bad Wi-Fi
Thin walls
Dirty rooms
Poor service
Construction
Mold
Bad air conditioning
Sketchy surroundings
I’m paying attention.
I also check what people say specifically about the neighborhood and location.
Check the Most Recent Photos
Professional hotel photography can make almost anything look good.
I like looking at recent traveler photos too.
That gives me a better sense of:
Actual room size
Condition of the property
Pool size
Views
Bathrooms
Common areas
How dated or updated the place feels
If the traveler photos and the official photos look like two different hotels, that tells me something.
Pay Attention to Transportation
I always think about how I’ll actually get around from the property.
I check:
Distance to major attractions
Nearest public transportation
Rideshare availability
Taxi access
Parking
Rental car needs
Airport distance
Traffic patterns
A hotel can look close on a map and still be a pain to reach.
Safety Matters
I do not need a neighborhood to be luxury or touristy.
But I do want to feel comfortable coming and going.
I research the area before booking and pay attention to:
Recent traveler reviews
Local safety guidance
Transportation options at night
How active the area is after dark
Whether the property has controlled access or front desk coverage
I also avoid relying on one random TikTok saying an entire neighborhood is either “completely safe” or “dangerous.”
I want a broader picture.
Consider the Airport, But Don’t Automatically Stay Near It
Airport hotels can make sense for:
Very early flights
Late arrivals
Overnight connections
Short business trips
But if I’m spending several days exploring the city, I usually would not stay near the airport just because it looks convenient on the map.
I’d rather stay where I’ll actually spend my time.
For Short Trips, Location Matters Even More
If I only have two or three days somewhere, I care a lot about location.
I do not want to spend an hour each way getting to everything.
On a short trip, I may willingly pay more to stay somewhere central because I’m essentially buying back time.
And vacation time is valuable.
For Longer Trips, You Can Be More Flexible
If I’m staying somewhere for a week or more, I may care about:
More space
Laundry
Kitchen access
A residential neighborhood
Better value
Feeling less touristy
On longer trips, staying a little farther out can make more sense because I’m not trying to maximize every hour.
Don’t Choose Based on the Hotel Alone
This is probably the biggest thing.
A beautiful hotel can absolutely make a trip better.
But I would not choose the hotel first and then build the entire trip around wherever it happens to be.
I start with the trip.
Then I find the property that supports it.
💡 SHANE’S TIP
Before I book, I pull up the property on a map and search directions to three or four places I already know I want to visit.
That usually tells me more about whether the location works than the hotel description ever will.
The Bottom Line
The best place to stay is not always the most expensive hotel, the trendiest neighborhood, or the place with the prettiest pool.
It’s the place that makes your specific trip easier and better.
Start with the neighborhood.
Look at your itinerary.
Figure out what amenities you’ll actually use.
Compare the total cost.
Then choose the property.
Because sometimes paying a little more for the right location can make the entire trip feel better.
Go somewhere. Make it worth it.