
Vacation rentals with a kayak in Lake Winnipesaukee
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Top-rated kayak rentals in Lake Winnipesaukee
Guests agree: these kayak rentals 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 spacesLocationAccess
4.94 out of 5 average rating, 124 reviews
Luxury Year-round Hobbit House w/ private hot tub
Fern Hollow 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.
Outdoor spacesLocationLaundry
4.92 out of 5 average rating, 132 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 spacesValueCheck-in
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.
Outdoor spacesLocationSkiing
4.99 out of 5 average rating, 337 reviews
Eclectic Lakefront Cottage on Great East Lake
Welcome to a relaxing stay on the shores of Great East Lake! The fall and winter are the definition of peace and quiet. Often you'll be the only folks on the cove! Come back inside after your outdoor adventures and warm your feet on the radiant slate floors .You can also prepare a home cooked meal in the vintage, fully applianced kitchen. This home is the perfect base for all your winter excursions, or enjoy family time inside with plenty of games, puzzles, ping pong, or air hockey! Enjoy!
Outdoor spacesValueSleep quality
4.99 out of 5 average rating, 186 reviews
Peaceful Lakefront Retreat
Rest, relax and recharge at this tranquil waterfront getaway on stunning Mirror Lake. Unplug from the hurry and enjoy this entire lakefront home in the privacy of a quiet street just minutes from downtown Wolfboro. Dining area, living space, kitchen and two bedrooms offer all the comforts you need with stunning lake views. Cozy cabin-like downstairs den has entertainment space, tables and seating for movies and games. Perfect spot for a quiet getaway to connect with friends, family and self.
LocationValueAccuracy
4.98 out of 5 average rating, 48 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.
LocationValueComfort
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).
LocationValueCondition
4.95 out of 5 average rating, 274 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.
LocationOutdoor spacesQuiet
4.98 out of 5 average rating, 127 reviews
☀ Fox & Loon lake house: hot tub/pedal boat/kayaks
Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting. The sunsets can be unbelievable!
ValueLocationHospitality
4.97 out of 5 average rating, 239 reviews
Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!
Experience ultimate relaxation with over 100 feet of sandy lakeside beach frontage, nestled among serene pine trees. This spacious lake house features: Open concept main floor 3 levels (3100 sq ft) for privacy Family & dog friendly Hot tub, kayaks, beach, game room, firepit & more! Ideal for large families wanting to share a vacation without compromising on privacy. Enjoy year-round activities and create lasting memories. Get 10% OFF for weekly or longer stays!
LocationOutdoor spacesLayout
4.98 out of 5 average rating, 210 reviews
Lovely cottage on Sunrise Lake, Middleton, NH.
A lovely lake-front cottage with a private beach on quaint Sunrise Lake! The house has a great view overlooking the water. Enjoy a beautiful morning view of the sun rising onto the lake with a cup of coffee or tea, grilling a tasty dinner on the deck, and toasting marshmallows in the fire pit for dessert. We also provide a double kayak so you can explore the mile-long lake from the easy launch point in front of the house.
Outdoor spacesLocationAccess
4.98 out of 5 average rating, 122 reviewsPopular amenities for Lake Winnipesaukee kayak rentals
House rentals with a kayak

Hebron Historic Farmhouse
Outdoor spacesLocationCondition
4.98 out of 5 average rating, 302 reviews
Winnipesaukee Lakefront Luxury unit #4 w Hot tub
LocationOutdoor spacesAmenities
4.99 out of 5 average rating, 97 reviews
Waterfront Chalk Pond | Fireplace | Kayaks
Outdoor spacesLocationCheckout
5.0 out of 5 average rating, 27 reviews
New Home Discount! Lakefront|Dock|Fireplace|XBox
Outdoor spacesLocationNearby
4.95 out of 5 average rating, 43 reviews
Luxury Lakehouse| Sunsets| Cen. Air| Private Dock
Outdoor spacesLocationGetting around
4.99 out of 5 average rating, 81 reviews
Lakeside Getaway - Lake Access/PrivateDock/Firepit
LocationOutdoor spacesHospitality
4.96 out of 5 average rating, 28 reviews
Hidden Kids Room | Kayaks | Fire Pit | Epic views
Outdoor spacesLocationHiking
4.98 out of 5 average rating, 48 reviews
Lovely home, across from lake, walk to Meredith
Outdoor spacesLocationCleanliness
4.97 out of 5 average rating, 66 reviewsCottage rentals with a kayak

Beautiful Lakeside Cottage
LocationOutdoor spacesBackyard
4.97 out of 5 average rating, 184 reviews
RiverPine Retreat - Clean & Bright Waterfront Home
LocationOutdoor spacesIndoor spaces
4.84 out of 5 average rating, 196 reviews
Gorgeous Romantic Lakefront Getaway
Outdoor spacesValueKitchen
4.99 out of 5 average rating, 121 reviews
“Stay Awhile in the Lake's Region”
LocationOutdoor spacesIndoor spaces
4.99 out of 5 average rating, 145 reviews
Completely updated detached cottage/Paugus Bay!
Outdoor spacesLocationAccess
4.94 out of 5 average rating, 125 reviews
Smokey Pines Camp
ValueLocationNearby
4.96 out of 5 average rating, 239 reviews
Waterfront Cottage Private Dock | Kayaks | Rowboat
ValueLocationAir conditioning
4.94 out of 5 average rating, 162 reviews
Private Beach, Lake Front, Family Friendly Cottage
Outdoor spacesValueAccuracy
4.96 out of 5 average rating, 136 reviewsCabin rentals with a kayak

Hill Studio
LocationOutdoor spacesCheck-in
4.98 out of 5 average rating, 116 reviews
Waterfront,Hot tub,Private dock,Freshly renovated
Outdoor spacesValueCheckout
4.82 out of 5 average rating, 191 reviews
Breezy Moose - A Frame Cabin/ Pet friendly
Outdoor spacesLocationCheck-in
4.94 out of 5 average rating, 157 reviews
Bear Cabin
LocationValuePool
4.9 out of 5 average rating, 181 reviews
Little House on the Lake in the Forest
Outdoor spacesLocationAccess
4.96 out of 5 average rating, 147 reviews
Cabin w/ Lake Access, Hot Tub, Kayaks, + Firepit!
LocationOutdoor spacesComfort
4.96 out of 5 average rating, 188 reviews
Beautiful Serene Lake/Ski House with central AC
LocationOutdoor spacesParks
4.87 out of 5 average rating, 252 reviews
The SugarShack at Sweetwater
Outdoor spacesLocationAmenities
4.97 out of 5 average rating, 181 reviewsDestinations to explore
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