




Discover the Oaktagon Tree House, where living with the forest takes on new meaning. Built around a living red oak named Annie, this octagonal tree house invites you up into the canopy on a 14-acre island just half a mile from shore on Annabessacook Lake in Monmouth, Maine. Here, birds provide the soundtrack and the lake glimmers below as you slow down, look outward through leaves and branches, and remember what it feels like to be held by trees.
The Oaktagon features 1 bedroom with 1 comfortable bed and 1 bathroom, accommodating up to 8 guests. Inside, cedar-scented air, a cathedral ceiling, and sunlight filtering through the canopy make the space feel both grounded and magical. Sleep soundly in the queen bed in the sleeping loft, made up with extra blankets and comforter. Two futon couches convert to queen and full size beds in the living room. For a unique lounging experience, clip the indoor hammock right to the tree in the living room. A small woodstove turns cool evenings into cozy ones, perfect for cooking, creating ambiance, or taking the chill off an evening breeze.
Getting here is part of the adventure, made easy with multiple options. Arrive by paddle, ferry, or your own boat, with free parking and island transportation included. Once settled, enjoy private access to the Oaktagon and shared access to the wider island: trails, docks, swimming spots, fishing areas, and canoes or kayaks ready to explore Annabessacook Lake. The island features over a mile of walking paths, benches, rope swing, and hammocks sprinkled throughout. Daytime neighbors may wander through shared areas as island tradition allows, but evenings are quiet and reserved for overnight guests.
Annabessacook Lake serves as your 1400-acre backyard of clear water and world-class bass fishing. The island offers hiking, swimming, cooking over open fires, sunset watching from Sunset Rock, fishing off the dock, and sauna lake plunging. Island transportation, canoes, kayaks, stand-up paddle boards with life vests, unlimited firewood, camp chairs, and dock space are all included.
The Oaktagon is pet-friendly for well-mannered dogs that get along with other pups and humans, remain bite-free, stay on leash during the stay, and whose owners take responsibility for any damages. Pet fees are $30 per night per pet, settled after reservation and screening.
Check-in is from 3:00 PM - 8:00 PM with multiple options: self check-in by bringing your own boat, paddling yourself in provided canoes or kayaks, or using free ferry service at 3pm and 5pm. Check-out is at 10:00 AM. Early arrival and late departure with luggage storage are available.
The Oaktagon welcomes families, groups, and anyone craving a reset rooted in life among the leaves. Come curious, pack light, and settle into canopy living where the trees do the talking and the island takes care of the rest. This is island life that's barely roughing it, even without grid electricity and running water, offering everything you need for a magical escape into nature.
This description is for informational purposes. Please verify all details, including amenities, policies, fees, and availability, on the booking platform before booking.
You’ll be staying in someone’s home, so please treat it with care and respect.

