



An idyllic space to live, rest, write, read, make art, and discover the magic of an island winter.
A full month to create.
This winter, give yourself the gift of serenity and inspiration in historic Hilltop Haven on Martha’s Vineyard - a curated winter residence for writers and creatives, where solitude, community, and creativity can comfortably coexist.
Imagine having an idyllic space to live, work, write, read, make art, rest and create - with interesting people nearby when you want to interact with them, and plenty of room to disappear into your own world when you don’t.
You’ll have your own private space - what you do with your time is completely up to you. The idea is to create a home with room for quiet and room for connection, creativity, joy and life.

Some days might be spent writing or curling up somewhere with a book. Other days you might wander into the kitchen and find someone making tea, share a long dinner, sit around a bonfire - or end up dancing in the living room.

We’ll have plenty of quiet time for reading, writing, and creating, with a natural rhythm toward more conversation, music, laughter, and gathering at other times.
Some shared spaces will stay quiet and unplugged - cozy places to read, write, think, or simply be without our phones.
There’s never an expectation to participate. Join everything, nothing, or anything in between.

Maybe you’re writing a book, working on essays, making art, or simply longing for space to create. Or maybe you just want a beautiful place to spend the winter on the Vineyard - a home where you can retreat when you crave quiet, share space when you crave connection, and be yourself in both.
Sharon Strimling · Host
Hilltop Haven is a beautiful, beloved, historic four-bedroom, three-bath home near the village, beach & ferry.



With generous shared spaces, a wood-pellet fireplace, large deck, two private yards and a fire-pit, it’s the perfect balance of spacious and intimate.
There’s also a separate detached studio - another beautiful space for writing, reading, making art, yoga, sound baths, and other creative pursuits.
Walking trails and gyms are nearby - and the water is just down the hill, with the beauty of the island right outside your door.

A full month on Martha’s Vineyard to settle into your creative life.
We’ve kept the price accessible, as our intention is to give you something that a weekend retreat can’t: time.
32 days • Sliding Scale • Scholarships available
$2450–$3450 all inclusive ($77–$109/night)
Inquire for shorter stays.
A writer, artist, or maker who wants a month away to settle deeply into their project - or simply into themselves. Someone for whom a long weekend retreat isn't enough to create the momentum and spaciousness their creativity craves.
Perhaps someone for whom writing or creating can sometimes feel a little too solitary, who loves the idea of having someone genuinely interested in what they're creating on their sunrise walk or tucked into the window nook.
This is the person who wants deep, unhurried time in a beautiful place,
with just enough of a container and just the right opportunities
for both connection and alone time.
Your stay includes sound baths, campfires, community gatherings, and cozy dinners, with opportunities to share whatever you’re creating, if you’d like.
Throughout the winter, we’ll also welcome guest speakers and creatives, along with a changing mix of optional activities and special offerings - from creative workshops and yoga to salsa evenings and more.
Anna is our Artist in Residence, a sound artist, writer, and community event organizer. She facilitates meditative sound baths, “Sonic Flow” creative workshops, community sound healing, peer support, and other intentional gatherings.
Justen is an author, poet, photographer, musician, father, and husband who has lived a rich, creative life. His life's service is in helping others find their voice and awaken creatively through writing.
Moira Convey Silva is a writing instructor, consultant and award-winning writer. Moira's writing focuses on features and essays, especially ones that relate to sustainability, and appears in the Boston Globe, Women’s Running, and Taproot.
Tsering is a Chaplain, Buddhist Lama
& Meditation Teacher, sharing teachings passed down through generations of Buddhist masters and students, supporting people of all backgrounds to cultivate resilience, clarity, and compassion.

Sometimes space is exactly what we need, and sometimes it helps to have great conversations, guidance, and inspiration along the way.
We have an extraordinary network of world-class coaches, writing mentors, and creative guides who are delighted to join us for conversations and talks throughout the winter - and some are also available for private sessions if you’d like someone alongside you to help bring your ideas more fully to life.