
Holiday rentals in Bear Island
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Top-rated holiday rentals in Bear Island
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Tiny Riverfront A-Frame w/ Mountain Views, Hot Tub
Welcome to 'The Alexander' @ Casa de Moraga! This tiny A-frame is nestled on the bank of Baker River w/ breathtaking views of the river & White Mountains. Full kitchen, bathroom w/ shower & living/dining area. Wake up in the loft bedroom & see the mountains & river from bed. Read on the couch & enjoy the gel fuel fireplace, take a swim or fish in the river - relax in your private hot tub on the deck overlooking the river! 10 min to Tenney MTN. 35 min to Ice Castles, Franconia, Loon & Waterville!

Trailside Stays - Tiny House in the Woods-Escape to Nature. Snow Owl
This charming and elegant little cabin will transport you into nature. The feeling of camping outdoors with indoor amenities. Part of the brand-new campsite, Trailside Stays that is conveniently located alongside the ski and mountain bike trails at Green Woodlands. This tiny house features 1 high quality queen-size bed, linens, kitchenette, large picture windows, bathroom with shower, heating and A/C, outdoor seating and grill top fire pit. Don't see your dates available? Check the other cabins!

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
Cliff House 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.

Log Home Meredith NH Pet Friendly Custom Fire-Pit
Log home getaway in Meredith NH, near Lake Winnipesaukee! 4-night minimum in July & August 3-night minimum on holiday weekends 2-night minimum in the off-season Enjoy a peaceful stay in our cozy custom log home —just down the road from Lake Winnipesaukee! Our home offers a wraparound deck, outdoor fire pit, and is pet-friendly for up to two dogs. Only 3 miles to downtown Meredith, close to beaches, hiking, restaurants, spas, and breweries. Perfect for a relaxing escape with family and friends.

Secluded Mountain View Cabin • Private Sauna
A real cabin in the North Woods secluded, private, and surrounded by open sky and sweeping mountain views that remind you why you came. This log-style retreat sits deep in the woods above Tamworth, fully equipped for comfort without sacrificing the rugged feel. Hike local trails, stargaze in near-zero light pollution, or sit by the fire pit with the mountains in front of you. The optional wood-fired sauna steps from the door is the perfect end to the day. Sauna available as a one-time add-on.

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.

Lovely Private Apartment Two Bedrooms
Private entrance & space. French doors large windows bright and airy. Lg living rm. Bed Rm w/queen. bed rm W/ king (two twins made up as king)all the time. Small kitchen w/micro coffee maker & fridge. NO STOVE only a single NuWave burner. Come & go as you please. This apartment is the lower level of our entire home. Very private and separate space. Enjoy 25 Acres of wooded land. Only 2 miles to town. Age 21 or older to book. We do not take children under 12 No parties NoPets No smoking.

Waterfront w Kayaks, Pool table, Pergola, Firepit
Waterfront location nestled in the heart of Laconia. Located on a river connected to Lake Opechee.. Less than 5 minute walk the lake, beaches and downtown. A beautiful 7 mile walking trail “wow trail” right near the property. 2 water facing decks, 1 front porch, 2 grills, fire pit under the pergola, Sundeck on the river, and 2 kayaks are provided with the home. Close to lake Winni, Weirs beach, Bank of NH Pavilion, Gunstock ski and many more local attractions all 10 minutes away

The Cottage on Paugus Bay- Lake Winnipesaukee
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!

Big Blue Chalet - A Mountain View Getaway
This large, private home located in Thornton, NH, was built in 2023 with sweeping 180° views overlooking the White Mountains. Just minutes off I-93, the home remains quiet and secluded thanks to its elevated mountainside setting. Popular local destinations include: Owl's Nest Resort - 10 min Franconia Notch - 20 min Ice Castles - 20 min Loon Mt - 20 min Waterville Valley Ski Mt - 25 min Cannon Ski Mt - 30 min Squam Lake - 25 min

Amazing Lake & Mountain views Gunstock Ski Chalet
Rustic Mountaintop Chalet nestled among the pine trees. Beautiful views of Gunstock Mountain Ski Area and of Lake Winnipesaukee from the large deck. Just minutes to the ski slopes in the Winter or to the lake in the Summer. A glass front wood stove for chilly nights, and an outdoor fire pit for roasting marshmallows. Board games, a foosball table, and an air hockey table for family fun. Quiet & peaceful!
Popular amenities for Bear Island holiday rentals
Other great holiday rentals in Bear Island

Winni Retreat Steps from the Lake!

Beautiful Lake Winnipesaukee w/ Dock!

Winnipesaukee Lakefront Cabin w/ Private Dock Slip

“Evergreen” 50 Acre Private Mountain Chalet

Lake Access | Prime Location | Designer Cabin

Flying Fish

9N Mountainside Cabin with Stunning Views!

Tiny Pine Lakefront Cabin, Dock, Kayaks & Fire Pit
Destinations to explore
- Plainview Holiday rentals
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- Long Island Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Pocono Mountains Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- White Mountain National Forest
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Story Land
- Squam Lake
- Weirs Beach
- Pats Peak Ski Area
- Loon Mountain Resort
- Mount Washington Cog Railway
- Tenney Mountain Resort
- Franconia Notch State Park
- Omni Mount Washington Resort
- King Pine Ski Area
- Snhu Arena
- Cranmore Mountain Resort
- Gunstock Mountain Resort
- Footbridge Beach
- Waterville Valley Resort
- Conway Scenic Railroad
- Cannon Mountain Ski Resort
- Ragged Mountain Resort
- Diana's Baths
- Funtown Splashtown USA





