Meet the Innkeepers

Four small Vineyard innkeepers bridge the tourist/Islander divide while hosting their visitors from afar, thriving on the conversations and connections.


Stanley Arend, owner + proprietor
Arend’s Beachfront Inn
65 Seaview Ave. • Oak Bluffs. • • 508-693-5148

Tell us about the history of the Beachfront Inn.

Our Victorian-style Oak Bluffs cottage was built in 1873 for the Tillinghast family — prominent merchants and ship owners from Rhode Island and New York — by well-known architect Samuel Freeman Pratt. It is one of six cottages remaining on the Island designed by Pratt. My family rented the house from friends in the 1950s, and later bought the house in 1959. It became our summer residence, as my mother, sister, and I spent all our summers here, wintering in Hanover. In 1982 we converted it to a guesthouse, with my mother running it until 2013. Then I retired a little early, and I took on the tasks of innkeeper.

Any major changes to the house?

We are in the process of adding mini-splits for heat and air. People think I need it, even with ocean breezes from across the road. We usually have one rough week in the summer with high heat and humidity. Customers want private baths and air conditioning. So I’m caving in. Right now we have six rooms and three baths. We’ll be creating at least one more bath. The two rooms up front have a connecting door, so I’m thinking of reorganizing to set that up as a suite.

We are keeping the historic details of the house … modernizing in terms of systems like AC and heat, but not changing any structural elements. Using original hardware when possible. I put in a foundation with a full basement three years ago for storage, a workshop, and possibly a TV room. Also, we are renovating a guest kitchen so I don’t have to prepare food in my own kitchen. Now we serve a continental breakfast.

How is running an inn different from your earlier career?

I was a chief financial officer (CFO) for state, local, and regional governments — including three Native American tribes — in four states: Massachusetts, California, Oregon, and Washington. Actually, I use all my CFO skills here, but on a smaller scale. As an innkeeper, I handle banking, credit cards, the inn’s accounting, taxes, network, website — all those chores come naturally.

What is the fun part?

I love the beach —- the water, the boats, fishing — now I can spend the whole summer here again. We are right across the road from the beach — the stairs are right there — it’s so simple. You don’t need a car. My son was here recently; my daughter is coming soon … my stepdaughter with children comes for Tivoli Day every year, and a lot of other family visit.

How has beach living changed since you were a child summering here?

Lifestyles have changed a bit: Back then, women came to the Island for the whole summer with kids, fathers came down on the weekends after work. I don’t think that practice works so much now.

We grew up across the street in the ’50s and ’60s at what used to be called the “pay beach.” It had lifeguards, a pier, rafts, a lunchroom, running water, toilets — like a summer camp — it was full-service. Summer visitors and Islander parents were comfortable sending their kids there with the dime it cost to get in. Someone would pay the town a certain amount to run it as a concession: They’d hire a lifeguard, staff the lunchroom, and collect the money. One year no one bid on it, and my mother agreed to run it, as she did for the last four years (I have the permit). When it deteriorated, the town did not replace anything. I made lifelong friends there who I see again when I return to the Island each summer. To answer your question, this is my home, this is what I do with my home. Even though we had a year-round house in Hanover, and I moved to the West Coast 20 years ago, this is home — why I come back.

Who are your customers?

A complete mix of 20-somethings to seniors, some with kids, and some bring relatives.

Lately I’ve been getting more long-term rentals: 21 days, 15 days; though we usually book for two, three, or four nights. We do have repeat people over the years; families came with young children. Now those children are coming with their children.

Elise LeBovit, owner
The Duck Inn
10 Duck Pond Way • Aquinnah • • 508-645-9018

How did the Duck Inn get established?

I bought 15 acres in Aquinnah with friends in 1980; we were all transplants from Virginia, and thought we would be living together here as an intentional community. Each person had their own area, and we had different buildings — all this was before the main house became an inn. I came here to do music with friends, to make a record … I sang, played saxophone, and wrote songs. I had that vision. Then one by one people left, and I thought I would do a spa here — a healing center, as I am a massage therapist. I needed to make money, so I started renting rooms; I have an old flyer dated 1986 that reads, “guesthouse, with private beach.”

I lived in the house, so it became a shared rental, with one bathroom — the house is quite different now, with six bathrooms.

Tell us about this great old house called the Duck Inn.

There are many different spaces here where people can feel at home, as the house is quite spacious. It is set due south, with the whole first level of stone. We had alternative energy specialists help redo the house — making it double-walled and double-insulated to become what is called a natural envelope house, due to the way the air flows. The north side is banked in the ground. The stone level is over 200 years old, and was a barn. This part of the house was the Belain family homestead; it was abandoned for about nine years before we purchased it. There were six rooms, old horsehair walls … deep steps to the basement; we added on an addition, with the house becoming passive solar, and kept the original floors.

Are you the sole innkeeper now?

Yes, I am running the inn alone. With COVID, I had a lot of cancellations last year. Families came with kids, who had been cooped up at home during COVID restrictions — joyful to run free with abandonment when they first arrived. Often during COVID I’ve been renting the whole house. The renters do their own breakfast. I leave the two shoulder seasons for my regulars, who have been coming here for years. I like the shoulder season because I get to know people, as I have more time, and I’m not run ragged.

Have you found it difficult to get help at the inn this summer?

It’s so hard to get help. Every innkeeper is saying that. The lucky part is that I’m small enough that I can run it myself if I have to.

What is the hardest part?

The hardest thing for me is to see my house abused … it’s nothing intentional, but people are on vacation, and may not be as careful as they could be. The screen door is left open, insects fly in. I like sharing my treasures, but am saddened when special things get broken.

Everybody is on vacation, and I’m working! They see you buzzing around, you are trying to help them relax … I’m like the duck floating on the surface, but underneath, my feet are moving fast … Just being graceful through that can be challenging.

Any future plans?

I love doing what I do. I’m way past my burnout time — I’ve been an innkeeper for over 30, 40 years. I tried to move to Portugal — I was going to leave the Island, as I had enough of local politics — then COVID happened. I dropped out of politics, and I’m much happier. I’m so lucky to have what I have, and I love sharing my vision … It lifts me up when guests appreciate the house and the visit. I’m single and live by myself, so I enjoy having people around, having great conversations. I really look forward to seeing my returning guests each year. I like having children stay at the inn, as I’m a big kid and animal person — we are kind of unique in that way.

Why the name Duck Inn?

When the stairs were here, when you walked upstairs you had to duck, and when you walked downstairs you had to duck. We are the ducks — me and my friends.

Freddy Rundlet + Catherine Keller, Innkeepers
The Look Inn
13 Look St. • Vineyard Haven. • • 508-693-6893

How long have you been an Innkeeper at the Look Inn?

My wife Catherine Keller and I opened the Look Inn 30 years ago on Oct. 1. My wife is also a therapist in town, so for the past three or four years, I’ve managed it by myself.

It’s been a lodging house since 1920.

I bought the house in 1980. I was living in Colorado from 1969 to ’88, where I raised my five kids and was a hospital administrator. I taught graduate college courses in marketing, gerontology, strategic planning, and organizational behavior. We moved here full-time in 1988–89. In 1991, we decided to get licensed as a B and B lodging house. I had opened Zapotec restaurant in Oak Bluffs in 1989, and we found that the ferry would get closed, and people would get stuck at the restaurant with no place to go … so they stayed here for the night. At the time it was against the zoning to have a business in a residential area. We had to go before the town board of appeals, explaining that sisters had run it as a lodging house since 1920, so we were grandfathered in.

What do you enjoy about being an innkeeper?

I quite enjoy meeting people — sharing with people the wonderful history of the Island and providing them with the opportunity to stay here at a reasonable cost. The New York Times noted in an article, “Freddy is the sandwich board of information for Martha’s Vineyard.” One thing I do differently from other innkeepers is I sit with each visitor, and help them determine what they would like to do while here: What are their interests? So I can advise them. I’m available by cell phone 24/7. I recommend restaurants, places of interest; on a rainy day, I may suggest a visit to the Martha’s Vineyard Museum, or one of our libraries. About half of our guests have been here before … People appreciate that they did have a good visit, and leave with a smile on their face. I do island tours occasionally, which are an enjoyable experience overall … The Vineyard really is a special place.

How did you acquire so much local knowledge?

For the first nine years of my life, I grew up with my aunts and uncles and cousins on the Forbes estate and farm in Milton. We also lived on Naushon, where we would shear sheep. My family rented a summer house in Oak Bluffs or Vineyard Haven each year — so essentially, I’ve been coming here for 72 years. Over that time, I have been interested in history. Four of my five kids are history majors.

Do you discover new things about the Island every year?

I make it a habit to go to yard sales: It gives me a chance to see homes and habitats all over the Island. I used to teach marketing at the University of Colorado Graduate School, so I find it interesting to see what people sell, what is disposable … what is desirable. It is a good release for me to go off Saturday morning to sales, sometimes with guests.

The other thing I’ve learned over time is that for the guests who come here, change is inevitable. It is interesting to see how people respond to change, whether it is due to COVID, or politics … it reaffirms my gratitude for living on Martha’s Vineyard. Visitors come to recognize they are caught up in day-to-day activities, and are not having much fun. Here on the Island, you are in a better position to be who you are: It’s diverse, and it’s safe here. In 30 years, after hundreds of guests to the inn, I’ve only had a situation once or twice that I’d prefer not to have. On the whole, people are good people.

Any surprises?

One surprise was that in the summer of 2015, without our knowledge, the New York Times began publishing an online series — cities and towns around the U.S. and world — and they included the Island: “36 Hours on Martha’s Vineyard.” We were one of two lodgings that were mentioned. Then in the fall of 2015, and for the next two seasons, we got a lot of inquiries and bookings from around the world. That opened it up for more visitors.

Who are your guests?

We’ve had some incredible guests who I’ve learned a lot from, listening to their stories and what they have to say. One in particular was a gentleman who was head of linguistics at Columbia University; he was having a boat built by Gannon & Benjamin, so he stayed with us for a couple of months. A fascinating character, hearing him speak to his colleague Noam Chomsky up at MIT. Another guest was a young cinema director and her photographer from public TV in France, who were working on a one-hour documentary on the history of African Americans on Martha’s Vineyard. Being a supporter of the African American Film Festival, it’s been enjoyable to have people of color stay here who come to attend the film festival on the Island. On a personal note, two of my kids are Black kids I adopted when they were a few months old; their lives have been enriched by being here and part of the Black community over the years and now.

All these experiences have made my life much more enriched, as well as my wife’s, doing what we are doing.

Biking and buses

We encourage guests not to bring a car, as we have an excellent bus system, and an excellent bike trail system we’d like to see expanded. We cater to a lot of bicycle people. Visitors can get a three-day bus pass, and we encourage them to hitchhike.

Any changes over time?

There have been some new challenges that are of concern: the advent of short-term rentals not only in Vineyard Haven, but across the whole Island. In years past we had neighborhood barbecues, and now we don’t know two-thirds of the people in the area, as new buyers may be investors rather than residents. There is increased traffic, increased noise, more landscapers and garbage trucks, parties, and lots of comings and goings. It used to be a quiet town; it’s no longer the case. This is a growing concern as the quality of life has significantly changed on this Island. And these short-term rentals also decrease the availability of year-round housing.

We need to call a time-out. It’s a shame that one of our largest businesses is landscaping. I’m all for change, but what we’ve seen with COVID and local politics is how fast things can change on a grand scale. COVID has had an impact, to the extent that people realized that they could hang out here for a while, many deciding to stay here year-round. And with vaccinations, people who were hemmed up in their houses are now coming to Martha’s Vineyard.

Any thoughts for the future?

I just celebrated my 75th birthday, and I still enjoy what I’m doing. I do all the beds, the food, the whole enchilada. I look forward to continuing, as it keeps me active and engaged, physically and mentally. I quite enjoy it … we’ll see what happens.

Keith Bassett, owner
The West Tisbury Inn
1070 State Road • West Tisbury • • 774-259-7271

How did you become an innkeeper?

When my mother retired from her real estate firm [Linda Bassett Real Estate], she purchased this property with my stepfather, rebuilt it, and ran it as Noah’s Ark B and B. More recently, just pre-COVID, she decided to put the house on the market, with no takers. I made her an offer, with the idea to rebrand the inn. She and my stepfather are elderly now, and I wanted them to have a chance to fully retire and live on the property. So I moved ahead to create the West Tisbury Inn — rebranded and upscaled.

I‘m a computer tech, founder and manager of Vineyard CompuTech for more than 20 years. I was doing well with that — I never thought I’d be an Innkeeper — but this was an opportunity that came to me, a win-win situation to preserve my parents’ legacy and to provide a chance for them to enjoy their golden years. They live in a cottage on the property.

I grew up on the Island, attended the University of New Hampshire, moved away for about 10 years; then moved back and raised a family. Now, here I am as an innkeeper. I have two daughters: My eldest is 21, living on the Vineyard, the younger is a student at Boston Conservatory for dance.

Have you given up your computer work?

People desperately need IT help, so I still help out when I can. Honestly, I wanted to do something completely different — do things my way, the new way. Everything is digital: on the computer, my booking engine, and the calendar. I want the business to be in the 21st century, with less paperwork. I got the website up quickly, and will be redoing it this winter. I was one of the first webmasters here on the Vineyard, back in the day.

Did you have help to open the inn at the beginning?

I consulted friends who own inns and other businesses here, and they gave me good advice, but no one warned me about the work! This is my first season — I’ve another month to get through, and then take some time to re-evaluate how to improve things. The busy pace is keeping me on my toes! I have never done so much laundry and still have dirty clothes! Running the inn is more than a full-time job. The popularity of the Vineyard has exploded, and there’s a shortage of beds out there. We’ve been very busy and full all summer. It’s never-ending, but luckily I do have some help. A Jamaican couple live here, and are like family, and we employ a great cleaning crew.

Any major changes to the house?

I did a lot of upgrades with the house, which dates back to the late 1700s and was the original rectory for the First Congregational Church of West Tisbury. It was moved to its present site from the original location near the graveyard off State Road. The front section was existing, nonconforming, but we expanded the back part. I started off with a spartan space, and built from there. We officially have six bedrooms, and have a license for five. Hopefully next season we will have six, when I take it to the next level of licensing. I wanted everything to comply with current town laws, as we are part of the historical district, and the town has been great to work with.

The new sign of the swallow?

I’m happy with the new sign and logo, which shows a barn swallow. My grandfather was a Micmac Native American of the Algonquin tribe. The swallow on the sign is from the Native American culture: When they saw swallows flying, it meant there was magic in the air.

What has been the biggest challenge?

I’ve been working with plants and computers all my life, so that part of the business is easy. Working with people has been challenging, but a blessing. I’ve found that one of the things keeping me going is the great people that I’ve been meeting. From all over the world — a lot of international travelers. I feel blessed, but it is a job that is never-ending. I’m married to the place now, also taking care of my mom and stepdad, so that’s keeping me close to home.

Any changes for the winter?

I’m looking forward to providing housing for some working people this winter, considering the housing shortage we have on the Island. We will only be offering winter housing, but it’s a beautiful property for someone to spend the winter.

During this off-season, I’ll re-evaluate, see what works, and decide on upgrades to be done. I need to do some exterior landscaping. I grow my own flowers and vegetables, and will do my winter planting. In season, I pick fresh flowers from my garden and put them in all the rooms.

Any ideas for the future?

I may get a license to provide breakfast next year. I’ve been in the food and wine industry as well, and was the wine director at Garde East in Vineyard Haven. On weekends, I get pastries from the Grey Barn farm — I jump in line early, brew some coffee, and let everyone know there are treats in the kitchen.

The people are what give me the fortitude to move forward and continue. These days, too, with so much fear out there, it means a lot to me to provide a piece of heaven here — a place for people to relax and forget the troubles of the world.