I Wish I Knew About These 7 Red Flags Before I Bought a Rental Cottage

When I bought a cottage in a coastal tourist town on the Rappahannock River in Virginia three years ago, I was buying into a dream I’d had for years. I grew up coming to this region. I have family in the area. My parents are five minutes away. All I had were nostalgic memories of smelling the brackish water, picking crabs and slurping oysters, and exploring the antique shops sprinkled throughout the region. 

Renting out the cottage I found was part of the equation of making the second home purchase affordable for me, but it’s not something I fully understood before jumping in headfirst. All of the wonderful times spent in the area didn’t include as much as a passing thought about running a business there. And, trust me, your perspective on a town and region starts to shift when you see it as a business owner and not just an occasional tourist. 

Here are seven things I wish I’d known before buying a rental cottage in a tourist destination.

We’re on the water with a pool so I knew, of course, that summer would be our high season. But I didn’t account for how different it would be season-to-season. Some months I expected to be busy are painfully slow. For example, May, which I thought would be a busy month, with beautiful weather and pre-summer prices, is always a struggle to book. It’s that lull between spring break and kids getting out for the summer, and people generally stay close to home. 

Similarly, while March often starts off with a flurry of inquiries, the potential guests are often in-state guests looking for an easy spring break destination. They often don’t realize that driving an hour towards the coast isn’t going to lead them to have a vacation where they can enjoy temperatures soaring into the 90s, so March tends to be slow as well.

There’s no way around the ups and downs, but I wish I’d done more research into understanding the rates and patterns rather than trying to figure it out by throwing darts at a board throughout the first year.

When it comes to things that neither my husband nor I thought we’d ever be doing, attending county board meetings would be at the top of the list. But if you’re in a tourist destination and you rent out your home, regulations on rentals will constantly be up for debate — even when the county depends on their revenue. 

There are absolutely bad actors that cause these discussions to happen, but the vacation rental industry in most tourist towns, including ours, isn’t anything new. Previously, many small tourist towns ran rentals as a cottage industry, operating primarily under the table. Airbnb has pushed it more into the limelight. Now we have to fight for our right to operate each time a new potential regulation comes up.

When one successful business launches, others will follow. We were one of the first cottages on Airbnb in our area, but, within a year, the map started to fill out — including several purchased by guests who’d stayed at our house (which actually makes me so happy!). 

The competition becomes self-selective quickly (it’s a harder process to run a vacation rental than most people realize!). However, it’s important to know that, even if you’re the first, you won’t be a runaway hit for long. Figuring out early how to differentiate your experience and hospitality is key.

Depending on where you’re located and whether you’re used to city or suburban living, it’s important to realize that the services you need to run your rental might not be readily available. We had the choice of two cleaners, zero pool services, and one electrician. If an emergency were to happen, we’re probably going to have to drive down to fix it ourselves. 

In the same vein, running a vacation rental means having your phone on all the time. Knock on wood, I’ve never gotten a 4 a.m. call, but my phone is always on, just in case someone gets locked out at an odd hour or something worse. If I’m going to be truly unreachable, I have to let the guests know, “Hey, I’ll be totally offline from 2 p.m. to 4 p.m. today.”

I looked at multiple cottages where it was clear the water was quickly approaching the house and, unfortunately, that is the reality of looking for property in many tourist towns. If it seems like too good of a deal, check the flood map. No amount of rental income can make up for your property being washed away in a few years. 

Consider everything from the climate and sea level rise implications on your own property to those within the nearest town — you don’t want to buy in a place that’s facing possible disaster.

Because I love being at the cottage, I’m there anytime it’s open for two nights or more year-round. But that doesn’t often happen in the summer, so I’m driving down on weekend days between bookings just to check things out. This is because I’ve realized that from June to September, I have to be on the property every two weeks at the very least, even when I can’t stay the night. Summer groups are rough on the house in a way that other seasons’ guests are not, and it’s mortifying to see something amiss and wonder how many guests also witnessed it that way.

Everyone’s cadence is going to be different. We self-manage our property (there’s no way I would turn over communication and branding to someone else!), but, even if you do have a property manager, you’re still going to have to go there yourself to get eyes on it occasionally. At the end of the day, it’s your home, and you’re the only one responsible for keeping it up to your standards.