We're thrilled to welcome Melissa Hessney Masters for the second edition of our Superhost Sessions, where we delve into the strategies, tips, and behind-the-scenes insights from the movers and shakers of the short-term rental world.

Melissa is the host behind Tanglebloom Cabin, a true off-the-grid hideaway in the woods of Brookline, Vermont. Melissa has meticulous crafted the guest experience at Tanglebloom so that her guests can connect to the nature that surrounds them.

Read the interview between InHouse CEO & Co-Founder Jono Schafler and Tanglebloom host Melissa Hessney Masters below. 

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Jono Schafler: Can you walk us through your journey into becoming an Airbnb host?

Melissa Hessney Masters: It was quite accidental, to be honest. I was managing my flower farm and floral design company, Tanglebloom, and we happened to have this little open-air cabin structure on our property that we had built for ourselves a few years before. My husband, Mike, and I would sleep out there in the summer because it's Vermont, so you don't have too many hot days. Air conditioning isn't really a thing. It was a nice place to relax for us.

Fast forward, we had a baby and weren't using the cabin structure much and were trying to think, what could we do with this? We hated that it was so lovely out here and no one was really getting to use it. We had a lot of friends that encouraged us to try it on Airbnb or Hipcamp. We thought it was a crazy idea, way too rustic, that no one would actually come pay to stay here. But long story short, we were wrong. We were very pleasantly surprised. As soon as we listed it, it was booking up like crazy. We had to go in and actually block time off just for us to be able to go out there and enjoy it.

Jono: Wow. Can you tell us a little bit about Tanglebloom Cabin?

Melissa: The cabin is literally open air. The sides are screened. It's small, 10 feet by 10 feet. There's a covered porch that gives about another four feet out. It has a clear roof, so you are completely immersed in the forest. It feels almost like a fairy tale, as many people describe it. There's a full-size bed, some lanterns, a bedside table, and not much else.

It's very minimal, the essentials of what you need to be out in nature and also be able to sleep in a real comfortable bed, not a tent, not on the floor, anything like that. Over the past seven years, we've added to the experience and the property quite a bit. So now we have an outdoor kitchen, an outdoor shower, and a wood-fired hot tub as well.

Jono: It sounds spectacular. Who did you speak with when you first were contemplating putting this out to the guest community to figure out how to set it up, to figure out whether it was going to be viable at all?

Melissa: I didn't have much of anyone to really speak to. I had a couple of friends who rented apartments connected to their home or that would rent spaces when they were not there, but I didn't know anyone that I could talk to that was doing anything like this.

I was drawing on my experience that I had back in 2010, right after Airbnb launched. I stayed in this little off-grid cabin by myself for a few days. Looking back, that experience really imprinted on me. Especially back then when Airbnb was brand new, what the host was doing was very unique. So that's really what I kept thinking back to, like, "what would they have done?" What did they have for the outhouse?"  "What did that look like? That's really what I drew on in the beginning.

Jono: And did guests get it right from the start?

Melissa: They do. We put a lot of work into qualifying our guests, making sure it's going to meet their expectations, that this is the experience they're looking for. We say you need a sense of adventure, which is true, especially if you're coming in spring or fall when it's a bit of a different experience.

So, we try to do a lot of work in that area. If there's ever any hesitation, it's fine. We'll refund you. We don't want anyone here that's not going to have a good time. It's good to stretch yourself, like the people who are on the edge, like, "I've never really been camping before, but my partner loves camping, and this seems like a great middle ground." That's the ideal situation. You have enough curiosity and are willing to put yourself out there a bit. But, someone who is completely freaked out by spiders or noises in the night, it's not a great experience for them.

"That's our thing: pack your clothes and stop at the grocery store if you want to do some cooking, and we take care of the rest."

Jono: Yeah, it seems like you've figured out some very sensible ways to mitigate those issues. And it sounds like you've had some relationship advice you've dispensed in the process. So, running a flower farm, I suppose you had some history in that.

Melissa: Yeah, exactly. Very cool.

Jono: What amenities on your stay that guests seem to be most attracted to?

Melissa: Our top amenity is the wood-fired hot tub, which we added a couple of years ago. That's been a standout. And, honestly, for us, it's been simple things like having an outdoor shower. People came into our house and used the bathroom, which blows my mind to say now, but it was very different.

Jono: And when it comes to food and coffee and things of that nature, do you play any role in helping guests to stock up their spaces?

Melissa: Yeah, for sure. We've always had freshly ground organic coffee ready for people and an assortment of teas. In the cooler months, like in the fall, we did hot chocolate for people. We always have basic pantry supply. So olive oil, salt, pepper, basic spices, pots, and pans, pretty much everything. I don't want you to have to bring anything. That's our thing: pack your clothes and stop at the grocery store if you want to do some cooking, and we take care of the rest.

Jono: How long have you been doing this? How long have you been a host of this space?

Melissa: We just finished our seventh season.

Jono: And have you thought about opening additional properties, or are you set with just this one?

Melissa: Absolutely. We're working on a new property. The hardest thing that's been for us with how popular the stay is and how compressed our season is, we're only renting about four and a half months of the year typically because it's outside, and we live in Vermont. Ski season is huge here, and we're located a mile off the main road to two major ski resorts. So, we are working on what will be a year-round stay, and I'm hoping that maybe by next year. But we'll see. We're doing most of the work ourselves, and it's really a labor of love. 

Jono: That sounds great. And it sounds like there's going to be a big reveal, so I won't try and get too much more information about that now. Is it going to be thematic in some regard?

Melissa: I will say there's going to be a lot of similarities. Still the focus on nature, connecting to nature. We're still trying to decide about our primary amenity, whether it be a hot tub again or we'll do a sauna, but something like that, something where you can really come and unplug. It's a similar forested setting really close to some wonderful hiking. So, it's going to be good. Another nature immersion retreat.

Jono: I saw that you won a number of awards for your property. Can you share with us how those came to be?

Melissa: Yeah. So, a couple of things in play. I honestly think, and this is just how I am and how I approach everything in my work, is to always be constantly trying to improve and do better and make things the best that they can possibly be. And then, I think we got the word out there from having a lot of positive reviews, hiring really great photographers to help us capture and share the space was really huge. So that people and places like Airbnb as a company - they knew that we even existed.

And then, really, when 2020 happened and people weren't traveling internationally and rural places suddenly became really attractive and places where you could have space and be outside, part of it was a function of being in the right place at the right time.

Jono: Have you had any outreach from other hosts looking for advice?

Melissa: Yeah, absolutely. I started offering consulting services on my website a couple of years ago, and I work one-on-one with both new hosts and hosts who have been doing this for a while and are really trying to optimize whether their calendars are a little sluggish, their bookings are down. They're trying to see what they should do for an amenity.

Markets are more saturated now, so how can they stand out? It definitely requires a little more intention and a little more work than it did say five years ago. Hosts also always reach out to me with questions via DM on Tanglebloom’s Instagram and I’m always happy to help out. 

"I honestly think, and this is just how I am and how I approach everything in my work, is to always be constantly trying to improve and do better and make things the best that they can possibly be."

Jono: What would you say are some of the most impactful things you as a host can do to drive additional bookings?

Melissa: The first one, which is just non-negotiable anymore, is having professional photography and even some videography. 

Keeping your listing optimized for SEO, and doing those updates seasonally - seasonally is something that affects a lot of the hosts that I work with. 

Doing your own marketing. Creating a website, having a social media presence, having a Google business listing - being out there so guests can discover your stay.

Jono: Are you still operating the flower farm as a business in conjunction with hosting?

Melissa: We are. It has changed a little bit over the years. We used to be a full-on production farm that served grocery stores and a CSA and a farm stand and weddings. We've really pared that down and focused a lot more on perennial flowers. Our main crop is peonies. And then we also do a lot of other sorts of perennial cutting gardens where guests can actually visit the gardens and cut a bouquet to take home with them. 

Jono: Sounds amazing. Is that an experience add-on you offer guests before the stay, on the stay? And if so, how do you actually conduct that transaction?

Melissa: A little bit of both. In the communication that goes to guests after they've booked, we mention that this is an experience we offer. We also have a few local products that they can buy, like a great locally made insect repellent. We tell guests something like “don't buy the junky stuff at the store on the way, we got the good stuff for you here.” [Laughs] 

Picking your flowers is an experience that's self-guided - guests they can choose to sign up for beforehand, which some folks do, or it's something once they get here, they decide they want to do. We also host a number of workshops during peony season, which is in June, that are open to the public that our guests can also jump in on those as well during their stay.

Jono: Last question for you, do you list the property outside of Airbnb with either any of the other sites or direct?

Melissa: We do Hipcamp as well. I would love to do direct bookings. The thing that we run into, which is common for hosts with similar stays, is getting enough insurance coverage to be able to do just direct booking. But I can't wait to do direct booking, and it'll definitely be part of our plan with our new property.

Jono: Ok actually last question. Do you have fun being a host?

Melissa: 100%. Yes. So much fun that a lot of times it doesn't feel like work, which I think is what we're all going for.

Barr Balamuth

Barr Balmuth is a staff writer at InHouse specializing in STRs.

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