Holiday rentals with a kayak in Lake Winnisquam

Find and book unique kayak rentals on Airbnb

Top-rated Accommodation with a Kayak in Lake Winnisquam

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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Guest favourite
An expansive wooden deck provides a welcoming space for relaxation, featuring multiple chairs and a table. A large umbrella offers shade, while the lake and trees are visible in the background, showcasing the natural surroundings and unobstructed views.
Home in Tuftonboro

20 Mile Bay - Tuftonboro - Lake View Pet friendly

Directly across from 20 Mile Bay on Lake Winnipesaukee in Tuftonboro. This 4 bedroom / 2.5 bathroom home sleeps up to 10 adults or 15 total people. The front deck overlooks the lake with unobstructed views. We provide kayaks, inflatable boats, & beach chairs for guests. We are pet friendly with $50 Fee only for pets registered at the time of booking. No unregistered pets allowed. The property is surrounded by conservation land. The Chandler Wild Park Trail has an entrance right in front o

Outdoor spacesValueBeach

4.94 out of 5 average rating, 124 reviews
Top Guest favourite
The spacious lakeside home is surrounded by lush trees, with a private dock extending into the water. A large deck provides outdoor seating, while a small sandy beach area invites relaxation. Sunlight filters through the greenery, creating a serene atmosphere for guests.
Home in Belmont

Lakefront Bliss|Private Dock & Year-Round Retreat

Escape to our serene Sargent Lake retreat, where year-round adventures and relaxation await.Enjoy fishing,swimming,and boating in summer or cozy up after a day of skiing, snowmobiling, or hiking in winter.Nestled in the heart of Belmont,NH,this spacious getaway features a private dock,stunning lake views,and plenty of space for family fun. Perfect for nature lovers,families,and those seeking a peaceful escape,our home is your ideal destination to create lasting lakefront memories in every season

Outdoor spacesValueLaundry

4.99 out of 5 average rating, 69 reviews
Guest favourite
A family lake house is positioned over the water, surrounded by lush trees. The two-story structure features multiple decks, providing space for outdoor activities. Colorful kayaks and paddleboards are visible along the dock, reflecting a peaceful lakeside ambiance under a partly cloudy sky.
Cottage in Alton

Lake Winnipesaukee/9min to Gunstock Mtn. Alton Bay

Family lake house built over the water on Lake Winnipesaukee. Great place for families and children. Only 9 min. to Gunstock Mountain for exceptional NH skiing. Close to many amazing hikes and set in the middle of world class foliage! Quiet, serene, and restful cottage that offers something for everyone. Whether is swimming, paddle boarding, and hiking in the summer or skiing, ice fishing and relaxing by the wood stove in the winter, this cottage will relax and revive you and your loved ones.

Outdoor spacesValuePool

4.94 out of 5 average rating, 87 reviews
Top Guest favourite
Cabin in Alexandria

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.

ValueLocationLaundry

4.99 out of 5 average rating, 337 reviews
Top Guest favourite
A warm and inviting living area showcases a stone fireplace framed by soft lighting. Two plush armchairs are positioned near a wooden coffee table. A cozy sofa adorned with a colorful blanket complements the wooden beams and walls, creating a tranquil atmosphere.
Cabin in Conway

The Conscious Cabin | Getaways + Retreats

Your cozy, mountain retreat awaits. Settle by the fire in this thoughtfully renovated log cabin, located in the heart of the White Mountains & less than 10 minutes from downtown North Conway's local shops, restaurants & adventures. Just 5 minutes from hiking Mt. Chocorua, paddling Lake Chocorua & exploring the scenic Kancamagus Highway. Featuring a bedroom, loft, full bathroom, kitchen, tea/coffee bar, fireplace, outdoor shower, firepit & more. Bask in the restorative magic of cabin living.

LocationValueAmenities

4.96 out of 5 average rating, 201 reviews
Guest favourite
Cabin in Barnstead

Dreamy Lakefront: Hot Tub, Kayaks, & Kid-friendly

This romantic & family-friendly lakefront chalet comes with a private beach, hot tub, kayaks & stunning views and is packed with amenities. It’s a serene home base to explore some of the best New England towns and is in the heart of the Lakes Region. Swim, kayak, bike a scenic trail, fish, hike, explore historic towns, farms & food scene, or simply grill with a view & play board games. We have poured our heart into making this a romantic yet very kid-friendly retreat (kids gear included).

ValueOutdoor spacesLaundry

4.95 out of 5 average rating, 274 reviews
Guest favourite
An outdoor patio area overlooks the serene waterfront, featuring a shaded seating arrangement with plush cushions and a coffee table. A gas grill is positioned nearby, accompanied by an umbrella providing shade. Lush greenery surrounds the space, enhancing the tranquil atmosphere.
Cottage in Belmont

Little Cottage - Private Lakefront

This lakefront cottage has it all! Charming 2-bedroom, 1-bath retreat in New Hampshire's scenic Lakes Region. Enjoy a year-round outdoor adventure or peaceful lakeside relaxation. 150ft of private waterfront to swim, kayak, or fish, a spacious yard with patios, grill, and a fire table. Nearby hiking trails, Gunstock Mountain, Highland Mountain Bike Park, and Lake Winnipesaukee. Just a short drive to top skiing resorts, restaurants, shopping, and more, your ideal base for every season.

LocationOutdoor spacesAccess

4.88 out of 5 average rating, 73 reviews
Guest favourite
A spacious porch features several white rocking chairs arranged to overlook the serene lake. Lush green trees are visible in the background, creating a peaceful outdoor setting. The wooden floor complements the inviting area, providing plenty of space for relaxation.
Home in Tilton

Winnisquam Lake House

Welcome to the beautiful Winnisquam lake house. The house has a beautiful view of the lake from the porch, a few steps down to a beach with clean shallow water, soft sandy bottom for swimming and kayaking, Adirondack chairs on the deck. This home has everything you need to enjoy the lake during the summer, ski slopes in the winter. Completely remodeled kitchen, a huge living room, 4 spacious bedrooms, total of 2000sqft living space. Enjoy kayak, boats, hiking skiing biking, and more.

LocationValueCondition

4.87 out of 5 average rating, 103 reviews
Top Guest favourite
Cottage in Tilton

Big Pine Lakefront Cottage, Dock, Kayaks & Firepit

Welcome to Big Pine Cottage. Your Summer or Winter Cabin Retreat Awaits You! Come relax and gather around the fire pit. Catch fish from the water’s edge. 100 feet of water frontage on a sandy bottom lake provides a great space to swim and relax. Explore the lake on our 4 person commercial grade peddle boat. We have 2 sit in style kayaks. Only a 5 minute drive from the Lake Estate on Winnisquam! Enjoy a peaceful and more tranquil experience when traveling for weddings and events!

Outdoor spacesLocationView

4.98 out of 5 average rating, 41 reviews
Top Guest favourite
A modern house with a sloped roof is surrounded by greenery. A spacious backyard features several teal chairs arranged around a fire pit, inviting relaxation. A white picket fence encloses the area, while a two-car garage is visible in the back.
Home in Meredith

Lovely home, across from lake, walk to Meredith

Hilltop Lakeview Retreat is a quiet and private modern oasis! Across the street from Lake Waukewan and a short walk to Main St in Meredith, NH, this 4 bedroom 3.5 bath home sleeps 12! Well behaved dogs are allowed with a pet fee. A 3 minute drive gets you to the Meredith town docks and Hesky Park. Stroll through the local shops and visit the restaurants for a culinary delight. Take in the Meredith Sculpture Art Walk, or Weirs Beach is only a 10 min drive.

Outdoor spacesLocationFamily

4.97 out of 5 average rating, 65 reviews
Top Guest favourite
A sandy beach area is depicted where four individuals sit along the water's edge, engaging with the lake. A small boat is moored nearby, and a floating platform is visible on the water's surface. Gentle waves lap at the shore, creating a serene atmosphere.
Cottage in Gilmanton

Private Beach, Lake Front, Family Friendly Cottage

Our clean private sandy beach, with a gentle slope is perfect for all swimmers. Sawyer Lake is a fun community. Enjoy our fun lakefront cottage with the perfect layout. 15 min. to Gunstock, Weirs Beach & Tilton Outlets • Kids will want to stay downstairs with a walkout, board games, TV, and 2 gaming systems [XBox 360° & Wii] with games. • Adults relax in peace upstairs with 2 private bedrooms, living area, & wood burning fireplace. Ask about weekends.

Outdoor spacesLocationLaundry

4.96 out of 5 average rating, 136 reviews
Guest favourite
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

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.

Outdoor spacesValueQuiet

4.95 out of 5 average rating, 139 reviews

Popular amenities for Lake Winnisquam kayak rentals

Holiday House Rentals with a Kayak

Cottages with a kayak