Vacation rentals in Bear Island

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Top-rated vacation rentals in Bear Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A rustic wooden cabin is nestled among snow-covered trees, with a clear path leading to its entrance. An American flag is displayed by the window, and fallen leaves around the cabin contrast against the fresh snow.
Place to stay in Moultonborough
4.97 out of 5 average rating, 141 reviews

The "Bear's Den" A secluded cabin

If your looking for a place to get away from it all and just relax this is the place for you! Located in the Northern Lakes Region on a major wildlife corridor this rustic hunting cabin has off the grid accessories including battery powered lights, outside cold shower with an outside sink and a outhouse. There are walking trails and abundant wildlife from deer, bear, moose and coyotes all of which you may encounter. The peepers will lull you to sleep at night. Pristine beach and hiking close by.

Superhost
An aerial view captures a serene lakeside setting, featuring a sandy beach lined with lounge chairs. Several boats are docked along the shore, while trees and buildings provide a natural backdrop, creating an inviting space for outdoor relaxation and activities.
Condo in Gilford
4.9 out of 5 average rating, 248 reviews

Great Condo near Gunstock, Lake Access & Concerts

Location and Amenities! We are the closest condo to the concert path on Misty Harbor!! 10 min from Gunstock, couple hundred yards from the Lake, 50 yards from Gilford concert stage back entrance. Access to Barefoot Beach, Lake Winnipesaukee, outdoor pool, tennis courts, grill high speed WiFi and more. 1 Bedroom studio and a pull out couch, sleeps 4 comfortably. Large bathroom and shower. Ski 10 min away or ice fish 150 yards away. Laconia Bike week only Minutes away! 1 Free parking spot

Top guest favorite
Cabin in Alexandria
4.98 out of 5 average rating, 175 reviews

Handcrafted A-Frame near Newfound Lake & Hiking

Unplug at Millmoon A-Frame Cabin just 2 hours from Boston - Recharge under the stars by the fire pit - Relax or grill on the back deck w/ forest views - Enjoy our pet-friendly working homestead - Ski at nearby Ragged & Tenney Mountain resorts - Explore hiking, biking & snowshoeing nearby at Wellington and 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.

Top guest favorite
A two-story home is set against a backdrop of lush greenery. The structure features a covered porch with large windows, and a well-maintained lawn leads up to the entrance. A driveway is visible, along with a garage at the base of the house.
Home in Gilford
4.92 out of 5 average rating, 133 reviews

5-Stars!! Cozy Home near the lake

Please answer our questions when requesting to book. If they are not answers, your request will be declined. Cozy home near the lake is a peaceful place to relax or adventure in the lakes region.The house is located right next to the Glendale Yacht Club and 0.3 miles or a 6 min walk (based on Google) to the Breeze Restaurant and water access at the Glendale Public Docks (no swim area). The house comes with a fully stocked kitchen, a grill, relatively fast internet and a 55" TV (no cable)

Top guest favorite
A spacious room showcases a unique sleeping area with adult bunk beds and a king-size bed on the opposite side. Decorative sliding doors feature a mountain design, while wooden flooring complements the light-colored walls and ceiling.
Barn in Laconia
5 out of 5 average rating, 105 reviews

Weirs Barn

This ain't your mama's barn loft apartment! We have spent years building one of the best places to stay in the Weirs. We aren't on the lake but we are near everything you want to do. Walking distance to bars, restaurants and Funspot! The Experience hits you the second you open your own private door. Floating barnwood king size bed, Adult Bunk Beds, Custom Full Murphy Bed, A bathroom staight out of HGTV, 81" TV, Custom Mini Kitchen, Laundry Room, Eat in Area Coffee/Tea Bar too much to list

Top guest favorite
A charming red schoolhouse, dating back to 1866, is surrounded by tall trees and a well-kept grassy area. The structure features white trim, large entrance doors, and a bell tower, evoking a sense of history and nostalgia.
Place to stay in Shapleigh
5 out of 5 average rating, 109 reviews

Romantic New England Historic Schoolhouse c1866

Winner of Maine Homes Small Space Design Award 2023 We are located on the private 80-acre Shapleigh Pond in the Southern Maine, an hour from Portland and two hours from Boston. Experience a bygone era in this restored Schoolhouse circa 1866 with many original details such as oversized glass-paned windows, wood plank floors, chalkboards, tin ceiling and more. Modern amenities such as fireplace, private hot tub, fire pit, gas BBQ and access to our pool (June-Sept), pond and tennis court.

Top guest favorite
The studio apartment features a queen size bed with a striped duvet and two large leather chairs. A wooden desk is positioned near a window, while the warm wooden floor adds to the inviting feel of the space.
Apartment in Wakefield
4.98 out of 5 average rating, 113 reviews

Clean, quaint studio apartment on small farm

Enjoy the Old Farm cottage, a studio apartment on our small homestead in the beautiful Lakes Region. It’s a perfect spot for couples, small families, or traveling nurses. We are within 20 minutes to many beaches, including Lake Winnipesaukee, and provide easy access to head south to the ocean or north to the mountains. You will have your own separate parking/entrance, but are welcome to enjoy our cozy fire pit, stylish treehouse, and backyard access to the network of snowmobile trails.

Top guest favorite
A wide view captures the expansive landscape, showcasing frozen bodies of water and distant mountain ranges. The snow-covered ground is visible, along with patches of greenery and trees. A clear sky dominates above, highlighting the serenity of the winter scenery.
Home in Meredith
4.93 out of 5 average rating, 249 reviews

Fall/Ski Fun: Spacious Home near downtown Meredith

My place is close to Mills Falls in Meredith, close to skiing, casual and fine dining, art shops, wineries, art and antique shops, just minutes to 2 - 4 hour hikes with great views of White Mountains and Lake Winnepesaukee, a beautiful Association Beach, and family-friendly activities. You’ll love my place because of the comfy bed, the kitchen, the high ceilings, its cleanliness, and coziness. My place is good for couples, solo adventurers, business travelers, and families (with kids).

Guest favorite
The custom log home is surrounded by lush greenery, showcasing a wrap-around deck with multiple seating areas. A hammock is positioned in the foreground, inviting relaxation. The sloped driveway leads to the entrance, enhancing the natural, tranquil setting.
Cottage in Meredith
4.86 out of 5 average rating, 208 reviews

Log Home Meredith NH Pet Friendly Custom Fire-Pit

I AM BACK MANAGING BOTH PROPERTIES 2025! :) FOUR NIGHT MIN STAY July and August! Holiday weekends 3 night minimum. Down the road from Lake Winnipesaukee in Meredith NH! COZY 1300 foot custom log home, pet friendly up to two dogs, custom outside fire-pit, wrap around deck, 3 miles to downtown Meredith NH, Near restaurants, Hiking, beaches, Spa's, breweries, etc. Enjoy a relaxing getaway with your family and friends. local town beach. No smoking in the home, no fireworks, no parties

Top guest favorite
A queen bed is centered against a warm brown wall, adorned with two modern pendant lamps above. Each side of the bed features a small, round nightstand. Natural light filters through the double windows, which are dressed with dark curtains, enhancing the room's cozy ambiance.
Guest suite in Meredith
4.91 out of 5 average rating, 331 reviews

Downtown! Studio w 3/4 Bathroom. Private Entrance!

This is one room with a queen bed and a 3/4 bathroom. Breakfast nook, mini-fridge, microwave, coffee maker. This room comes with it's own seperate entrance, private bathroom, and private patio (Patio is not open in the winter). Also we have off street parking for one or two cars. I am new to hosting, so for now please a two person max. Walking distance to downtown. Less than 100 yards and you are in the middle of downtown Meredith.

Guest favorite
The exterior view of a two-story cottage showcases a modern design with light-colored siding and multiple windows. A welcoming front staircase leads to the entrance, complemented by landscaped grounds and stone details. Nearby, similar cottages form a cozy community atmosphere.
Home in Laconia
4.87 out of 5 average rating, 127 reviews

The Cottage on Paugus Bay- Near I-93 and Skiing

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!

Guest favorite
A scenic view of the lake is framed by tall pine trees, with clear blue water visible in the background. The smooth pavement leads toward the shore, where neighboring properties are seen along the waterfront.
Home in Laconia
4.97 out of 5 average rating, 115 reviews

Lakeside Getaway~EV Charger~15mns to Gunstock

Discover Your Lakeside Escape at Lake Winnipesaukee! Welcome to your perfect home away from home in beautiful Laconia, NH! This brand-new, luxury 2-bedroom condo in the heart of Paugus Bay offers the ideal retreat for couples, small families, and outdoor enthusiasts alike. With stunning lake views, access to a day dock, and modern comforts throughout, it’s the perfect base to experience the very best of New Hampshire’s Lakes Region.

Popular amenities for Bear Island vacation rentals

  1. Airbnb
  2. United States
  3. New Hampshire
  4. Belknap County
  5. Meredith
  6. Bear Island