
Vacation rentals with a kayak in Lake Winnipesaukee
Find and book unique kayak rentals on Airbnb
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
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.
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.
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.
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!
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.
4.98 out of 5 average rating, 48 reviews
Luxury Lakehouse| Sunsets| Cen. Air| Private Dock
Crystal clear Rust Pond contemporary waterfront home with picturesque lake views from every angle and multiple decks. Your vacation home has central AC for hot days and a cozy gas fireplace and central heat for chilly nights. Rust Pond is an oligotrophic lake with excellent swimming, SUP boarding, kayaking, fishing, etc. The home offers privacy in a peaceful lakeside setting, yet is just 10 mins from Wolfeboro downtown restaurants, farm to table fare, art galleries and boutique shopping.
4.99 out of 5 average rating, 80 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).
4.95 out of 5 average rating, 274 reviews
Waterfront Chalk Pond | Fireplace | Kayaks
Birch Hill House on Chalk Pond is a bright waterfront retreat for every season. Cathedral ceilings and expansive windows frame glowing sunset water views while a cozy electric fireplace warms crisp evenings. Enjoy hiking, birding, kayaking, fishing, and swimming from the private beach, then unwind by the fire pit or relax on the spacious deck. Watch for loons and eagles and explore nearby Birch Ridge trails, Powder Mill snowmobile routes, and the Lakes Region. 90 minutes from Boston.
5.0 out of 5 average rating, 27 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!
4.98 out of 5 average rating, 210 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.
4.97 out of 5 average rating, 65 reviews
Winnipesaukee Lakefront Luxury unit #4 w Hot tub
This 2Bed/2Bath waterfront luxury cottage w stunning sunset views is part of a yr around resort located at the Paugus bay of Lake Winnipesaukee. This Unit is right at lakefront. It sleeps up to 6. It offers full kitchen, quartz, steel appliances, washer/dryer, BBQ grill, Kayaks, private hot tub all season, Boat Slip fee- $200, Pet Fee -$100 (Max 2 pets), 2 Cars Tandem Parking, No Trailer! Near to Gunstock Ski Resort, Weirs Beach, NH Bank Pavilion
4.99 out of 5 average rating, 97 reviewsPopular amenities for Lake Winnipesaukee kayak rentals
House rentals with a kayak

Hebron Historic Farmhouse
4.98 out of 5 average rating, 302 reviews
Lakeside Getaway - Lake Access/PrivateDock/Firepit
4.96 out of 5 average rating, 28 reviews
Peaceful 4 bedroom lakehouse retreat
4.98 out of 5 average rating, 45 reviews
Gram's House
4.85 out of 5 average rating, 20 reviews
Hidden Kids Room | Kayaks | Fire Pit | Epic views
4.98 out of 5 average rating, 48 reviews
Fall Lakefront Luxe I Cozy I Bonfire I Hot Tub
5.0 out of 5 average rating, 29 reviews
Camp Oscar Waterfront Lake Winnipesaukee
4.9 out of 5 average rating, 10 reviews
The Lake House in Acton
5.0 out of 5 average rating, 45 reviewsCottage rentals with a kayak

Beautiful Lakeside Cottage
4.97 out of 5 average rating, 184 reviews
☀ Fox & Loon lake house: hot tub/pedal boat/kayaks
4.97 out of 5 average rating, 239 reviews
Gorgeous Romantic Lakefront Getaway
4.99 out of 5 average rating, 121 reviews
RiverPine Retreat - Clean & Bright Waterfront Home
4.84 out of 5 average rating, 195 reviews
“Stay Awhile in the Lake's Region”
4.99 out of 5 average rating, 145 reviews
Private Beach, Lake Front, Family Friendly Cottage
4.96 out of 5 average rating, 136 reviews
Waterfront Cottage Private Dock | Kayaks | Rowboat
4.94 out of 5 average rating, 161 reviews
1B Cottage w/Kayaks-Lake Winnipesaukee View/Access
4.9 out of 5 average rating, 240 reviewsCabin rentals with a kayak

Waterfront,Hot tub,Private dock,Freshly renovated
4.82 out of 5 average rating, 191 reviews
The Conscious Cabin | Getaways + Retreats
4.96 out of 5 average rating, 201 reviews
Hill Studio
4.98 out of 5 average rating, 116 reviews
Cabin w/ Lake Access, Hot Tub, Kayaks, + Firepit!
4.96 out of 5 average rating, 188 reviews
Bear Cabin
4.9 out of 5 average rating, 181 reviews
Beautiful Serene Lake/Ski House with central AC
4.87 out of 5 average rating, 252 reviews
Breezy Moose - A Frame Cabin/ Pet friendly
4.94 out of 5 average rating, 157 reviews
Little House on the Lake in the Forest
4.96 out of 5 average rating, 147 reviewsDestinations to explore
- New York Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Quebec City Vacation rentals
- Jersey City Vacation rentals
- Portland Vacation rentals
- Newark Vacation rentals
- Mont-Tremblant Vacation rentals
- Salem Vacation rentals
- Providence Vacation rentals
- Newport Vacation rentals
- York County Vacation rentals
- Family-friendly rentals Lake Winnipesaukee
- Waterfront rentals Lake Winnipesaukee
- House rentals Lake Winnipesaukee
- Condo rentals Lake Winnipesaukee
- Rentals with breakfast Lake Winnipesaukee
- Rentals with lake access Lake Winnipesaukee
- Rentals with a sauna Lake Winnipesaukee
- Townhouse rentals Lake Winnipesaukee
- Lakehouse rentals Lake Winnipesaukee
- Cabin rentals Lake Winnipesaukee
- Rentals with a hot tub Lake Winnipesaukee
- Private suite rentals Lake Winnipesaukee
- Cottage rentals Lake Winnipesaukee
- Pet-friendly rentals Lake Winnipesaukee
- Rentals with pools Lake Winnipesaukee
- Hotel rooms Lake Winnipesaukee
- Beachfront rentals Lake Winnipesaukee
- Rentals with beach access Lake Winnipesaukee
- Apartment rentals Lake Winnipesaukee
- Rentals with a kayak New Hampshire
- Rentals with a kayak United States
- Sebago Lake
- White Mountain National Forest
- Ogunquit Beach
- Hampton Beach
- Wells Beach
- Squam Lake
- Story Land
- Weirs Beach
- Long Sands Beach
- Short Sands Beach
- Loon Mountain Resort
- Willard Beach
- Pats Peak Ski Area
- York Harbor Beach
- North Hampton Beach
- Scarborough Beach
- Cape Neddick Beach
- Footbridge Beach
- Mount Washington Cog Railway
- Snhu Arena
- Jenness Beach
- Cranmore Mountain Resort
- Hills Beach
- Gooch's Beach





