
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.

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
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
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
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
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
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
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
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
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
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
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
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 reviewsPopular amenities for Lake Winnisquam kayak rentals
Holiday House Rentals with a Kayak

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!
Outdoor spacesLocationAmenities
4.98 out of 5 average rating, 210 reviews
Winnipesaukee Lakefront Luxury unit #4 w Hot tub
ValueLocationParking
4.99 out of 5 average rating, 97 reviews
Hidden Kids Room | Kayaks | Fire Pit | Epic views
LocationOutdoor spacesSleep quality
4.98 out of 5 average rating, 48 reviews
Waterfront Chalk Pond | Fireplace | Kayaks
LocationOutdoor spacesAir conditioning
5.0 out of 5 average rating, 27 reviews
Gram's House
Outdoor spacesLocationCheckout
4.85 out of 5 average rating, 20 reviews
Luxury Lakehouse| Sunsets| Cen. Air| Private Dock
LocationOutdoor spacesCleanliness
4.99 out of 5 average rating, 80 reviews
Lake cabin, private beach, ski 10 min
LocationOutdoor spacesBeach
5.0 out of 5 average rating, 16 reviews
Peaceful 4 bedroom lakehouse retreat
LocationOutdoor spacesAmenities
4.98 out of 5 average rating, 45 reviewsCottages with a kayak

Lovely cottage on Sunrise Lake, Middleton, NH.
Outdoor spacesLocationLayout
4.98 out of 5 average rating, 122 reviews
Cozy cottage near Gilford, lake access & hot tub!
LocationOutdoor spacesComfort
4.88 out of 5 average rating, 133 reviews
Completely updated detached cottage/Paugus Bay!
ValueOutdoor spacesCondition
4.94 out of 5 average rating, 125 reviews
Waterfront Cottage Private Dock | Kayaks | Rowboat
ValueOutdoor spacesWi-Fi
4.94 out of 5 average rating, 161 reviews
Kolelemook Cottage!
Outdoor spacesLocationGetting around
4.96 out of 5 average rating, 147 reviews
Smokey Pines Camp
LocationOutdoor spacesRiver
4.96 out of 5 average rating, 239 reviews
Large Private Lake House
Outdoor spacesLocationCleanliness
4.95 out of 5 average rating, 255 reviews
Charming Mountain View River Cottage w/ Pvt. Trail
LocationValueCondition
4.96 out of 5 average rating, 193 reviewsCabin rentals with a kayak

Hill Studio
LocationValueCleanliness
4.98 out of 5 average rating, 116 reviews
Little House on the Lake in the Forest
Outdoor spacesLocationAmenities
4.96 out of 5 average rating, 147 reviews
Breezy Moose - A Frame Cabin/ Pet friendly
LocationValueQuiet
4.94 out of 5 average rating, 157 reviews
The SugarShack at Sweetwater
Outdoor spacesValueAccuracy
4.97 out of 5 average rating, 181 reviews
Beautiful Serene Lake/Ski House with central AC
ValueOutdoor spacesBiking
4.87 out of 5 average rating, 252 reviews
Bear Cabin
LocationOutdoor spacesSkiing
4.9 out of 5 average rating, 181 reviews
The Glamp Camp at Sweetwater
LocationOutdoor spacesBeach
4.93 out of 5 average rating, 153 reviews
Beautiful private cabin on Big Squam Lake
Outdoor spacesLocationBarbecue
4.86 out of 5 average rating, 112 reviewsDestinations to explore
- Apartment rentals Lake Winnisquam
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- Rentals with a kayak Belknap County
- Rentals with a kayak New Hampshire
- Rentals with a kayak United States
- White Mountain National Forest
- Ogunquit Beach
- Wells Beach
- Squam Lake
- Story Land
- Weirs Beach
- Loon Mountain Resort
- Pats Peak Ski Area
- Footbridge Beach
- Snhu Arena
- Cranmore Mountain Resort
- Dartmouth College
- Tenney Mountain Resort
- Franconia Notch State Park
- Pleasant Mountain Ski Area
- Gunstock Mountain Resort
- Conway Scenic Railroad
- Ragged Mountain Resort
- Bear Brook State Park
- Attitash Mountain Resort
- Echo Lake State Park
- Crawford Notch State Park
- Diana's Baths
- Waterville Valley Resort





