Bear Island Retreat | Dock + Kayaks | Winni

Escape to a private retreat on Bear Island, where peaceful lake living meets classic New Hampshire charm. Surrounded by water and nature, this lakefront home offers direct access to Lake Winnipesaukee, beautiful open views, and a rare sense of calm that makes it easy to truly unplug.

Days here move at a different pace. Mornings begin with the soft glow of sunrise reflecting across the lake, coffee in hand as the water stays perfectly still. Afternoons invite you outside—swimming from the shore, paddling along the island’s edge, kayaking, or simply relaxing and listening to the quiet that only island living provides. With no road noise and no rush, the lake becomes the focus of each day.

Inside, the home offers a comfortable, welcoming space designed for easy lake life. It’s a place to gather after time on the water, share meals, play games, and wind down as the evening light fades. Whether you’re traveling as a couple, family, or small group, the home provides everything you need for a relaxed and memorable stay.

Although Bear Island feels wonderfully removed, you’re still close to the best of the Lakes Region. A short boat ride brings you to Meredith, where you’ll find local restaurants, shops, ice cream stands, and seasonal events. It’s the perfect balance—true island privacy paired with easy access to town.

From warm summer swims to crisp fall foliage reflected on the lake, this Bear Island retreat offers a one-of-a-kind experience guests remember long after they leave. Quiet, scenic, and deeply peaceful, it’s lake living at its finest.

Please Note: Bear Island is only accessible by boat. Guests must arrange their own transportation to and from the island.If you need to arrange a boat ride to and from the island, we’re your direct point of contact. We’ll handle the logistics so all you have to do is arrive, exhale, and let island time take over.

🐾 Dog-Friendly Property
This is a dog-friendly home, we love hosting well-behaved pups! To keep the space comfortable for all guests, only dogs are permitted (no cats or other pets).
Please let us know in advance if you’ll be bringing your furry friend, and be sure to add your dog to the reservation, as a pet fee applies.
✅ 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.