Island Escape, Views + Kayak, Winnipesaukee

Imagine waking to the best sunrise on Lake Winnipesaukee, arriving by boat to a quiet, rustic, minimalist island retreat where life slows down. A shaded front yard leads to your private dock for sunbathing, paddleboarding, kayaking, and peaceful days in a calm cove. Roast s’mores by the fire, grill under the stars, hear the loons, explore island hiking trails, and enjoy the simple magic of true island living.
Morning begins with soft lake light spilling across the water. The stillness of a quiet cove. Coffee in hand. Loons calling in the distance. The dock waits just outside your door, and the lake feels like it belongs only to you.
Welcome to your private Bear Island retreat. A place where days unfold slowly, shoes stay forgotten, and the rhythm of the water sets the pace.
This warm, inviting cabin is made for connection. Inside, the open living space invites movie nights on the couch, laughter over card games, and delicious BBQ dinners that stretch into stories and stargazing. The kitchen is equipped for lakeside breakfasts and sunset feasts, and the outdoor dining table becomes the gathering place, framed by glowing water views.
Cozy sleeping spaces offer deep rest after long lake days:
Two quaint, peaceful bedrooms with queen beds, and a loft space for the adventurous island goers.
Outside is where the magic truly unfolds. Your private dock becomes your front porch to the lake. Mornings start with paddleboards gliding across glassy water. Afternoons drift by in kayaks and island hiking adventures. Evenings belong to the deck, the grill, and golden-hour skies that feel painted just for you. The Blackstone flattop and charcoal grill set the stage for lakeside dinners while the sun melts behind the island.
Wander the island trails, explore quiet coves, float under the sky, or simply sit still and let the world slow down.

This isn’t just a cabin.
It’s sunrise rituals.
Dockside coffee.
Barefoot dinners.
Lake-quiet nights.
Island time.
Come write your Bear Island story.
Lake Winnipesaukee is waiting.
No shoes in the cabin, guests must leave cabin how they found it, no loud music to respect neighbors.

Good News! Your stay includes coverage for accidental damage and mishaps. We take your safety and security seriously, and this property has special local compliance requirements of a signed rental agreement and ID verification. To make this easy for you, we use a secure and very simple, app-free platform called Happy Guest. It is not an app, and you do not have to sign up for an account — it’s a safe and secure website. It also gives you a guest portal with all the info about the home and all of my favorite local spots.