Vacationland: Maine and the Iconic Summer Rental


Maine’s iconic nickname, “Vacationland,” has always conjured images of the mass migration of leisure hungry tourists, mad and ravenous for the pine scented forests and picturesque lakes, quiet in their solitude,  a lone loon baying off in the distance, its haunting call echoing off the fir lined shores, silhouetted against the stygian night sky, a velvet curtain of the deepest coal, the backdrop for a milky way performance of phosphorescent brilliance played nightly. What is even more iconic is the summer rental. Whether it be sea side cottage or lake home cabin, Maine has always had a  strong history of summer rental homes. In the popular novel penned by Sinclair Lewis, Babbitt, the ordinary, dull, humdrum, George F. Babbitt, finds himself in Maine, vacationing in a cabin by a lake, like so many city-dwellers found themselves in the 1920s, escaping the fast paced city life for only a brief moment of wilderness and rustic charm. In The Seven Year Itch starring Tom Ewell and Marilyn Monroe, the first few minutes of this movie is narrated by a congenially voiced man, describing how droves of urbanites evacuated the city for the cool shores and lakes of Maine, finding a summer cabin or cottage within which to escape the doldrums of the urban island of concrete. This wasn’t just a hollywood invention, or an author’s imaginings, but this was a legitimate past time for many urban dwellers, seeking an escape from the sweltering city streets that were like pools of liquid tar, boiling and sticking to soles of small children’s shoes, as they ran from shadow to shadow, trying to alleviate the oppression of the sun overhead. And this tradition has continued today, as I-95 becomes a congested corridor of automobiles, like salmon swimming upstream, all fighting to get to their destination first.


And then there is my own family who participated in this summertime ritual in the 1940s and 50s. My mother, along with her mother and father, sisters and brother, all stayed at Curtis’ cabins on Graham Lake in Ellsworth, a fifteen mile, muddy, man-made lake, with eery stumps reaching out from the depths of the lakebed, the tops of those trees visible in the murky black waters, left to rot in perpetuity–a watery grave bestowed upon them when the Union River was contained by earthen dam at the south end of the now deep mere. My family fled  the hot steamy labyrinth of steel and glass, stone and mortar, cement and brick, of New York City, more specifically Park Slope in Brooklyn, a five story brownstone, which becomes more of a brick oven for human cooking than a habitable home in the months of July, August, and September. To bring this full circle, it was in 1986 when we ventured back up to Maine from Long Island, New York–Cutchogue to be exact–crossing the Long Island sound on that early morning ferry, our wood-panneled station wagon deep in the recesses of that steel floating beast, like Noah trapped within the belly of that gargantuan whale leviathan, as we plied the waters of the Long Island Sound to the Connecticut shore. We too, like so many others before us in a long standing tradition, booked a cabin in the woods of Maine, our trip bringing us to Brooklin, on the Blue Hill Peninsula at Carter’s Cabins–Naskeag Point only a stone’s throw away–down a long dirt driveway, atop a cliff looking out to Long Island, across the cold waters of Blue Hill Bay.


While serene lakes, rocky jagged coast lines, and picturesque woodland scenes are all facets that create appeal for tourists coming to Maine, so too does the summer rental home, a home away from home, because, like the saying goes, “Maine. It’s The Way Life Should Be.” The cabin, cottage, or home, becomes as much a part of the Maine experience as is Acadia National Park. Vacationers traveling to the Pine Tree State seek an experience that is different from their everyday life, and in doing so, seek out an authenticity of the rustic beauty and living which drew them here in the first place. Whether it is a cabin hidden deep within the woods, a small bungalow nestled against the dunes of the roaring ocean, or a home in the downtown of some fishing village, located distally along some peninsula reaching into the ocean, these are not just places of rest, but they themselves become part of the vacation. I myself, when I travel, search out two different kinds of places. If I am on the go–a fast, quick, cover as much ground as I can type of vacation–then I find cheap hotels, hostels, and transportation that allows me to sleep while moving–whether it is trains, planes, or automobiles–but, if I am staying in one place, exploring a whole area, I prefer homes of which I am then living within the community, not removed in some towering, hulking mess of steel and glass, a destination for the casual observer who chooses luxury over experience, over authenticity.


Maine has always been a tourist destination, viewed as the wild, vast frontier of Northern New England. I remember as a child sitting in class, my friends gathered around, asking me questions about my summer trips to Maine. It struck me as odd when they posed queries such as, “Do you have running water?; Do you see bears all the time?; Have you seen a Moose?; and, are there grocery stores?” Maine had become such a common, known part of my life since I was four years old, that I was more confused on how people could think these utterly ludicrous notions. It was as if the world stopped at the New Hampshire border–and for the majority I am sure it was Massachusetts–and for many it was a mystical land, shrouded in mist, a fog of imaginary looming over this territory of northern woodland pine forest. But for me, Maine was no different than any other place I had ever visited. Yes, it was wooded, but it had paved roads–for the most part in 1986–and we had running water, electricity. And there were even grocery stores, better than the one we frequented on Long Island. The radio still captured stations–the music outdated at times–and although our cabin did not have a television, we knew they existed in Maine, as we had stayed at a hotel in Ellsworth which had a color set in our room. The way people imagined Maine as a frontier stuck with me all those years, and now I wonder if that isn’t the draw of the cabin, the home rental, to be part of that wilderness, to have the full experience of authenticity.


Sitting outside the Redcup Coffee Shop, on a cool, breezy morning in Boothbay Harbor, the smell of the ocean wafted along the crisp air while our cups of coffee steamed, swirling like acrobats high above three rings below. The onyx liquid like a piece of obsidian, polished brightly, and formed to follow the curves of the paper cup, invigorated me, a comforting and societally accepted form of addiction. Enjoying the morning, and observing my surroundings, I couldn’t help notice Boothbay is still a quaint fishing village. Although touristy shops and restaurants dot  the waterfront, the community has struck a happy balance between the visitors wants and the residents who reside there. Although one could argue that Boothbay does not have the mountains of Acadia, the draw of a national park, at the same time, it is a popular tourist destination which has attracted in the past Princess Diana and other dignitaries and celebrities to its charismatic, yet tranquil locale. But on this day, sitting outside in the crisp air, enjoying my cup of steaming java, I noticed that it was not crowded, but instead there was a pleasant, steady trickle of tourists, enjoying the seaside town.

In contrast to  another tourist hotspot in Maine, like Bar Harbor, Boothbay Harbor is tranquil, quiet, yet has a pulse that comes out when the mood strikes. So it was fitting that I met with Jason Schlosser here on this quiet street. A business development representative for Vacasa–a vacation rental management company with 2400 rentals in eleven states, including locales in Belize, Panama, and Mexico– Jason manages the operations within the Downeast region of Maine. Vacasa, a vacation rental management group which takes all the work out and hassle out of the rental process for the homeowner, manages all aspects of rentals from booking reservations, adjusting prices, and hiring housekeepers who maintain and clean the residence. Essentially the homeowner owns the residence, and Vacasa does the rest. I met with Jason to discuss summer rentals in Maine, and what this represents for the Pine Tree State’s tourism economy.

According to Vacasa’s data on average vacation rentals, the average cost per night for a home that can sleep twelve is $196.51 per night, while the average cost per hotel room in the state of Maine in 2014 was $116.00; and from personal experience, if you are staying around downtown Portland, it is more. Schlosser noted that many tourists that book through Vacasa are searching for an authentic experience, and want their domicile to be more than just a place to sleep, but one where their vacation blends with the rental they choose. Their company encourages homeowners to inject a little bit of themselves into their homes, giving the renter a fleeting glimpse into the lives that these walls encompass. He warns the homeowner looking to rent, this does not mean decorating the house with pictures of the grandkids and family heirlooms, but if you are a musician, let them know it, and leave some tasteful pieces that represent you and your musical inclinations. If you have books on shelves, leave them. Decorate your home so it is representative of you, and the area they are visiting. Make it warm and comforting, make it quirky and interesting, but don’t make it out to be fake and austere. The most important bit of advice Jason has for any resident who would considering renting their home for a vacation rental–whether through online sites, a rental company, or on their own–is decorate the home so it is an authentic experience. Make it part of the vacation, instead of just a place to sleep. Think about what would attract someone to your home, and why it reflects a different experience, because those looking for a vacation rental have done the hotels, and said no thank you.



A few block away from the downtown section of Boothbay Harbor, in a quaint little neighborhood sits a beautiful white house, resplendent in its stark white edifice, with flat rock stacked walls surrounding simple seaside cottage gardens. This home, “Fleur de Lis,” is a radiant abode which made me envious as I wended my way around the property. The homeowner, having renovated this simple cape, has taken the care to pay attention to detail, and has made this home an experience that I envisioned myself sitting out back by the garden, reading a book, glass of scotch in hand, as the cool afternoon fog rolled in off the harbor, a buoy bell tolling far off in the distance, as seagulls called out for their kin through the enshrouding mist. Jason pointed out that they encouraged the homeowner to keep her books on the shelves, and decorate with the many other trinkets that she would not worry about leaving behind. This house was captivating, and as I explored the nooks of this house, I found confederate currency tucked inside an old tobacco tin, a beautiful antique kitchen table, and a beautiful secret that is not advertised on the site–I cannot ruin the surprise on here, only those that rent will find this out. This homeowner, working with an employee of Vacasa to maximize the experience for the renter, found a niche for this home, and in fact, has been featured in prestigious home magazines. What Jason pointed out to me, your house doesn’t have to be perfect, or so well decorated it graces the pages of a periodical, but instead, have a flare that creates an environment that is the vacation.




Vacasa is not the only rental company on the market, and to name a few I know of, VRBO and Airbnb are both steeped in this industry as well. I have used airbnb with stellar success, and have browsed VRBO many times. This article is not an endorsement for Vacasa, but illustrates there are many options for the home owner when deciding whether or not to rent their home as a vacation rental. Jason noted that many homeowners enter into rentals with a romanticism, such as the ownership of B&Bs, which speak to certain people. The problem is, sometimes people get in over their heads, not realizing how much time just fielding emails, queries, and booking reservations takes out of their day. This does not take into account any trouble shooting and repairs that must be accomplished while the residence is rented, and then accounting for a cleaning crew to come in and turn over that rental immediately for the next incoming group. Also, as if always a fearful option, what happens if someone trashes the home. As a self-renting homeowner, how do you solve this problem? Vacasa takes credit card information and will charge the renters for any damages, and also, has proprietary computer technology that will screen guests and will cancel reservations if they find a party scheduled at that residence–which has happened due to a posting on Facebook which the software picked up before it occurred.



Overall, the promise of renting one’s home to tourists can be very appealing in a state that touts itself as Vacationland. On the television show, Vacation House for Free, Matt Blashaw is sought out by couples who wish to purchase a vacation home, but rent it out during the peak season, paying their mortgage and taxes down, keeping it available for other times of the year to visit. This is the same philosophy  Jason emphasizes to his clients. Having a vacation home which is only used at certain times, can be rented at others, deferring the cost of owning the home, and in essence, stimulates the local economy. Can this philosophy work in all locations, probably not. The obvious factor to take into account would be geographic location.

So remember if you are ok with someone sleeping in your home or vacation house, and decide to take the next step–either on your own or with Jason’s help–modernize, yet keep the old elements, make the home an authentic experience. When deciding how to decorate, think to yourself, would I want to spend my time here? Does this home represent where I am visiting? People travel to areas for a certain experience, to be immersed in a certain aesthetic, always keep that in the back of your mind. You wouldn’t build an igloo in the desert, would you?

Disclaimer:  I was not paid, or work for Vacasa. Jason Schlosser and Kalli Bean, were both generous enough to take the time to communicate with me through personal interview and email on this topic.





David Jester

About David Jester

David Jester lives in the Midcoast region of Maine. He received a masters degree in American and New England Studies from the University of Maine. David is a full-time firefighter/paramedic and writer, who maintains another blog He travels the world, but chooses locales that many would never consider for vacation. The world is full of many different and unique places, why not see them all?