
Vacation rentals in Bear Island
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Top-rated vacation rentals in Bear Island
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Cozy A Frame Cabin
Discover Your Dream Getaway at Our Enchanting A-Frame Cabin in Danbury, NH! Hike lush forest trails, paddle across sparkling lakes, or hit the nearby slopes for seasonal adventure. After a day outdoors, kick back on the spacious deck, fire up the grill, and dine under the stars. Whether you're planning a romantic escape or a fun-filled family getaway, this hidden gem offers the perfect blend of comfort, charm, and natural beauty. Escape the ordinary—book your unforgettable Danbury retreat today!

Luxury Year-round Treehouse with private hot tub
The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

Amazing Lake/ Mountain View’s Gunstock Ski Chalet
Rustic mountaintop chalet nestled among pine trees with beautiful views of Gunstock Mountain Ski Area and Lake Winnipesaukee from the deck. Minutes to Gunstock for winter skiing/tubing and summer zip lining/ mountain coaster, and to Lake Winnipesaukee. Cozy glass-front wood stove for chilly nights, outdoor fire pit for marshmallows, a grill for summer cookouts. Includes board games, foosball, and air hockey for family fun. Quiet, peaceful, and surrounded by nature—perfect year-round getaway!

Modern Chalet by Mt. Sunapee with Spa
Just 4 minutes from Mount Sunapee Resort and Lake Sunapee beach, our newly rebuilt luxury cabin offers a clean, modern escape with high ceilings, a stunning window wall, and a spacious backyard with a hot tub. Unwind in two cozy queen bedrooms, a spa-like bathroom with heated floors, a fully equipped kitchen, and fast Wi-Fi. It’s perfect for romantic getaways or relaxing retreats. This is the second luxurious cabin crafted by us with love & care. Photos by Chris & Pam Daniele / @dirtandglass

Peaceful Lakefront Retreat
Rest, relax and recharge at this tranquil waterfront getaway on stunning Mirror Lake. Unplug from the hurry and enjoy this entire lakefront home in the privacy of a quiet street just minutes from downtown Wolfboro. Dining area, living space, kitchen and two bedrooms offer all the comforts you need with stunning lake views. Cozy cabin-like downstairs den has entertainment space, tables and seating for movies and games. Perfect spot for a quiet getaway to connect with friends, family and self.

Mountain Lodge with Private Sauna
Escape to Darkfrost Mountain Lodge, less than 2 hours from Boston - Gather under the stars by the fire pit & garden - Relax or grill on patio with woodland views - Enjoy a pet-friendly working homestead - Ski at nearby Ragged & Tenney Mountain - Explore hiking, biking & snowshoeing nearby at Wellington, Cardigan Mountain State Parks, AMC Cardigan Lodge Looking for options? Visit my Airbnb Host Profile to explore our 3 available cabins: Millmoon A-Frame, Black Dog Cabin, Darkfrost Lodge.

Beautiful Lake Winnipesaukee w/ Dock!
Beautiful Home On Lake Winnipesaukee right in the heart of Paugus Bay. Included in your rental, our dock will accommodate a boat up to 30ft & upon request we have availability for one jetski lift! Lake Winnipesaukee Is the largest lake in the state. Enjoy the sunsets, mountain views, waterfront restaurants, live music, sand bars, homemade ice cream, shopping & more. Ski or snowboard at Gunstock Mountain, explore nearby snowmobile routes. Our home offers year round endless adventure.

Cedar Hideaway: Walk to Pond, 15m N. Conway
Sip coffee on the screened porch listening to the wind in the pine grove. This modern cedar cabin is your sanctuary from the summer crowds, yet only 15 mins to the bustle of North Conway. Walk to the pond for a dip or read a book in the hammock. Equipped with fast WiFi and a fully stocked kitchen and charcoal grill. Cathedral Ledge and many hikes a short drive away. A tranquil, shady escape for those looking to slow down and breathe or your launchpad for White Mountain adventures.

G-Frame Off-Grid Cabin Retreat + Sauna
Located atop a ravine, centered on a 24 acre estate, in rural NH, this spot is a cozy retreat in nature with a few present day necessities. Our Cabin is a unique A-frame/Salt box combo that we call the “G-Frame” (designed and built by us). The interior space is open and airy. There are a few large windows allowing nature to be part of your experience indoors. In the cooler months bring firewood for the woodstove and sauna.Plenty of land for outdoor activities.

Luxury Glamping NH - Geodome Sanctuary
Escape to a private luxury sanctuary retreat tucked behind a small family owned Christmas tree farm in Sutton, New Hampshire. This adults-only geodome features a private hot tub, wood-fired cedar sauna, cold plunge, hammock and fire pit beneath a sky full of stars. Created for couples seeking rest, connection, and renewal, it’s the perfect place to slow down, reconnect, and experience the beauty of New Hampshire. Just 80 minutes from Boston, yet a world away.

Serene Garden Private entrance, room, bath & patio
Beautiful guest suite with private entrance and patio overlooking peaceful garden views. One queen bed, bathroom with walk in shower. Small Refrigerator/freezer with, Keurig coffee maker and a variety of coffees available. 2 GUESTS ONLY - No Air Mattresses 14.5 miles to Gunstock Resort, 1.2 miles to bay, shopping, restaurants, movie theater, & grocery. 5 min. (1.8 miles) to Church Landing, 18 min (9.6 miles) to Bank of NH Pavilion.

Fall Foliage HQ- The Cottage on Paugus Bay
Enjoy peace and tranquility along the shores of Winnipesaukee's Paugus Bay. This Brand New waterfront Cottage is one of the most popular in Lakes Region and is central to all the Lakes Region has to offer. Along the western tip of the lake, easy access to I-93. The community comes with a day dock and easy access to boating and other lake activities. Come back year after year. We love repeat guests and offer discounts for second stays!
Popular amenities for Bear Island vacation rentals
Other great vacation rentals in Bear Island

Camp Looney: Lake Access & Pet Friendly

Winnipesaukee All Season Getaway

Snowy Acres

Lake Access | Prime Location | Designer Cabin

Winnipesaukee Lakefront Luxury unit #4 w Hot tub

Lake Winnipesaukee/9min to Gunstock Mtn. Alton Bay

Ridge Retreat • Skiing + Hiking • Hot Tub + Sauna

Luxury Tiny Home Getaway-LILAC Home
Destinations to explore
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- Sebago Lake
- White Mountain National Forest
- Ogunquit Beach
- Wells Beach
- Squam Lake
- Story Land
- Weirs Beach
- Pats Peak Ski Area
- Loon Mountain Resort
- Mount Washington Cog Railway
- Footbridge Beach
- Dartmouth College
- Tenney Mountain Resort
- Snhu Arena
- Franconia Notch State Park
- Cranmore Mountain Resort
- Omni Mount Washington Resort
- King Pine Ski Area
- Gunstock Mountain Resort
- Ragged Mountain Resort
- Conway Scenic Railroad
- Pleasant Mountain Ski Area
- Waterville Valley Resort
- Diana's Baths





