
Vacation rentals in Bear Island
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Top-rated vacation rentals in Bear Island
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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

Harolds Camp: Lake Winnipesaukee Waterfront w/dock
Cute, clean and cared for 1900's cottage literally on the shores of Lake Winnipesaukee offering you the chance to relax and get away. This 934 sq ft waterfront camp is located in the quaint town of Alton Bay, NH and offers an open concept living/dining w/ fireplace insert for heat/ambiance, kitchen, 2 bedrooms, bath and an amazing screen porch. Our guests have said it is truly something special and that view! This is lakeside living the way it was meant to be. Host is a licensed NH Realtor.

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

Stickney Hill Cottage
Stickney Hill Cottage is nestled up and away from the hustle of daily life. A quiet get-away for you to reconnect and make new treasured memories with a loved one. Located close to amenities in Campton, NH at the base of the White Mountains, this unique handcrafted cottage has been lovingly built using local wood , much of it from the property it is built on! Whether this is your base for adventure or you plan to stay in the entire visit, Stickney Hill is your special get-away location!

Winnipesaukee Lakeside Retreat W/Dock
Our summer schedule is now live! This chic, three-bedroom, 2.5-bath waterfront home provides a serene retreat to unwind and enjoy all that the Lakes Region has to offer. With breathtaking lake views from almost every room, you'll feel inspired and at peace! PLUS A DOCK FOR YOUR BOAT AND JETSKI! The prime location is minutes away from fantastic restaurants, shopping, skiing, and entertainment. With endless exciting activities just a stone's throw away, your perfect getaway awaits

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

The Back Haus! Dock space available.
The Back Haus, 2 stories; filled with character; 3 AC bedrooms ; 1 queen, 1 full, a bunk room w/ 3 single & a pullout single. Large LR with 70" TV & pool table. Galley kitchen. Washer/dryer. Separate work space. 2 BR; 1 newly renovated w/walk in shower, 2nd w/Victorian bathtub. Private beach, walk to dock, outdoor seating & firepit. Docking/Jet ski lift at additional cost. Ellie Mae & Jethro are your concierges. Bank of NH Pavilion 1 mile away. Gunstock 7 min away.

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!

The NEST Haven awaits you.
You found your ultimate relaxation spot, sandy beaches on Rock Haven Lake (only 800' from your front door) infrared Sauna (accessible through the secret door) , 3 person hot tub, outdoor (seasonal) shower, luscious king seize bed, 6' TIPI daybed, firepit, outdoor tipi swing, a balcony and deck to enjoy the peaceful neighborhood. Round shower and deep claw foot soaker tub. Enjoy, relax and let your soul ponder.

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!

The Lakes Region Log Cabin
The Lakes Region Log Cabin is located near Lake Winnipesaukee, Lake Winnisquam, Gunstock Mountain, Tanger shopping outlets, NH Bank Pavilion and more, for fun in every season! Relax at the house or enjoy one of the many activities in the Lakes Region. We do full cleaning turnovers between guests and all linens are laundered professionally; if you have any questions, please reach out!

A-Frame in Gilford
Our cozy A-Frame home is just minutes from Gunstock Mountain Resort and the Gilford town beach at Lake Winnipesaukee. Three bedrooms can accommodate up to 6 guests, with 2 queens, and 1 full, and 1.5 bathrooms. Outdoor area includes a hot tub, fire pit, brand new large deck with dining table/seating, and a gas grill. 1 mile from Bank NH Pavillion and 5 miles from Weirs Beach.
Popular amenities for Bear Island vacation rentals
Other great vacation rentals in Bear Island

Waterfront Chalk Pond | Fireplace | Kayaks

Misty Harbor - Learn 2 Ski!

Bear Island Retreat! Best Sunrise on the Lake!

Lakefront Piece of Heaven! Weirs Beach

The Vista, of the White Mountains

Cozy 2-Bed Lakefront Weirs Beach

Cheerful 4-bedroom home with private beach access

Relaxing hidden gem in Wolfeboro
Destinations to explore
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- White Mountain National Forest
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Squam Lake
- Story Land
- Pats Peak Ski Area
- Weirs Beach
- Loon Mountain Resort
- Mount Washington Cog Railway
- Cranmore Mountain Resort
- Tenney Mountain Resort
- King Pine Ski Area
- Franconia Notch State Park
- Gunstock Mountain Resort
- Omni Mount Washington Resort
- Cannon Mountain Ski Resort
- Ragged Mountain Resort
- Diana's Baths
- Waterville Valley Resort
- Funtown Splashtown USA
- Bear Brook State Park
- Footbridge Beach
- Pleasant Mountain Ski Area




