How choosing the right place to stay quietly reshaped the way we travel.
☕ QUICK SIP SUMMARY
- We plan trips around character-filled stays rather than packed itineraries.
- Small towns offer the space and quiet that make these stays feel restorative.
- The accommodations themselves often become the most memorable part of the trip.
About five years ago, I had an unexpected shift in how I think about travel. My husband and I were celebrating our second anniversary, and he was in charge of booking the stay. He picked a bed and breakfast in a random town in Pennsylvania Dutch Country. Not somewhere I would have chosen, and definitely not somewhere I had on my radar.
To my surprise, this was not your typical B&B. This place was next level. He has a go-big-or-go-home tendency, so naturally he booked the best room with the best view and access to the rooftop. Yes, a rooftop. In a small town.
That stay changed something for me. It showed me a version of luxury that was not flashy or city-centered, but quieter and just as thoughtful. Since then, we have leaned into spending the bulk of our travel budget on where we stay. When we go somewhere, we usually splurge on a place with a strong sense of character. A cool theme, great views, B&B-style service, or some combination of all three. It is almost always in a small town or quieter setting because that suits us best.
This approach works well for us because, frankly, we are not great planners. We get stressed easily and don’t do well with itineraries. These types of stays have helped remove a lot of pressure. We can fully enjoy the space, rest instead of rush, and explore town only if and when we feel like it. There is no fear of missing out and no feeling like we are doing travel “wrong.”
Why This Travel Style Works for Us
If you remember the couple from National Lampoon’s Christmas Vacation who lived next door, that is who we sometimes feel like, not to sound overly posh. They loved the finer things, and so do we, but without the performance of it all. We like comfort, beauty, and quality, but not at the expense of actually relaxing.
We have found that these kinds of stays allow for exactly that. They give us permission to slow down and fully enjoy the place for what it is, do a few things in town if we want, or do nothing at all. That balance has led to some of our favorite travel moments.
Some of our best discoveries have happened when we had no strict plan. Wandering downtown without an agenda has brought us to local shops, small markets, historic buildings, and viewpoints we never would have found otherwise. Those moments tend to stick with me because they were unplanned. They just happened organically.
And when we head back to where we are staying, it is always nice to return to a place that feels like part of the experience rather than just somewhere to sleep. Over the years, we have stayed in rooms with fireplaces and hot tubs, rooftop access with views and fire pits, and even spaces with grand pianos available to play freely. As musicians, that detail alone has made certain trips unforgettable, especially with a kind of natural reverb you just do not get at home. There is usually plenty to do, or plenty of space to do very little, which is often the goal.
The Quiet Pull of Small Towns
I grew up in a small town with a population of about 7,000, so maybe it makes sense that I am drawn back to places like this as an adult. I have lived in several major cities and loved that phase of my life, but they are no longer where I want to vacation.
Not all small towns are created equal, but the ones we gravitate toward tend to have a few things in common. Charm, a handful of good restaurants, actually good coffee, which is essential for both of us, and some sense of local culture or beautiful surroundings. Most of all, they have a quietness to them. We usually look for towns a couple of hours outside major hubs so we feel removed from the pace of city life without feeling completely isolated.
A Stay That Stayed With Me: Grandma’s Cottage, Wisconsin
One of the most memorable examples of this travel style came during a recent trip to Wisconsin to visit my family. Through a family friend, we heard about Grandma’s Cottage in Muskego. The name alone did not immediately sell me, but the reviews were glowing, and curiosity got the best of us.
About 45 minutes from my parents’ house, in Muskego, Wisconsin, a town of roughly 27,000 people outside the Milwaukee area, we drove down a long driveway lined with trees and bright fall leaves. At the end were three buildings. One had a charming archway and path leading to the cottage. The others looked like old farm structures.
As soon as we stepped inside, we were completely taken by the place. It leaned fully into the grandma theme, and I loved it. Patterned, kitschy curtains, cozy furniture, and an old but functional TV with a DVD player. No streaming services. No shortcuts. Since it was Halloween, we leaned into it completely and made a Walmart run to buy a horror movie on DVD.
Inside the main room was a loft reached by a steep staircase, furnished with a bean bag, books, and a guest book meant for writing love letters, since this was a common destination for anniversaries and romantic getaways. Behind the main room was a spacious bathroom with a spa tub, double sinks, and a shower. Outside, there was a covered fire pit area with chairs and blankets ready to go, along with a fireplace inside.
Later that night, we realized one of the farm buildings was open to guests. Inside was an entire floor dedicated to old-school games like billiards, foosball, and video games. It felt like stepping into another time zone. The property itself was surrounded by animals. We could see horses and llamas nearby, and two sweet-natured cats roamed the grounds, though they never came inside.
The morning made the place even more special. Breakfast was delivered directly to the cottage by the owners themselves. I met the woman who runs the property and her husband as they walked up together, set everything down, and headed back hand in hand. It felt less like a rental and more like being welcomed into someone’s world, even briefly.
I spent time in the loft writing my husband a love letter that I hope we find again someday. As we drove away, the trees lining the driveway were lit, making the whole place feel even more magical.
A Different Kind of Luxury in Oregon’s Countryside
Another stay that stands out in our travels was a standalone cottage located on the grounds of a wedding venue outside Portland. It turned out to be a standalone cottage on the venue grounds, with its own small yard and a sense of privacy that made it feel separate from everything else.
The setting was beautiful. Swan-filled ponds, bridges, and carefully maintained grounds full of flowers and greenery. The cottage itself was beautifully decorated with a modern feel and had everything you would want in a full home, including a living room, kitchen, bathroom, and two bedrooms. It quickly became our home base.
We were free to walk the venue grounds and quickly understood why it was used for weddings. We spent evenings ordering dinner in so we could fully enjoy the space, watching Christmas movies as part of our annual tradition of celebrating our July anniversary with a little Christmas in July. I even brought along a small box of decorations and made us matching sweatshirts, treating the cottage like a temporary home rather than just a place to stay.
I wandered through the wooded areas and found quiet spots near the water, while during the day we were close enough to Portland to explore and visit some must-see specialty coffee shops. It felt like the best of both worlds.
What I’ll Always Remember About These Trips
When I look back on these trips, it is the stays themselves that stay with me most clearly. I remember each one in detail, partly because the schedules were simple and partly because the accommodations were so distinct. Each holds a specific memory tied to rest, discovery, and being fully present.
This way of traveling has reshaped what luxury means to me. It is not about excess or spectacle, but about choosing places that allow time to slow down and the experience to unfold naturally. More often than not, it is the place we stay that ends up shaping the trip long after we have returned home.
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