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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.

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Treehouse in Sanford

4.9 out of 5 average rating, 480 reviews

Luxury Year-round Treehouse with private hot tub

The Canopy 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.

Cabin in Barnstead

4.95 out of 5 average rating, 197 reviews

Scenic Lake and Ski Chalet: Hot Tub & Dreamy Views

This romantic & family friendly lakefront chalet comes with a private beach, hot tub, camp fire, and stunning views. It’s a serene home base to explore everything the Lakes Region has to offer. Mid Apr-Oct we also provide kayaks and paddle board. Enjoy the beach, swim, kayak, bike, fish, hike, or explore quintessential New England towns and food scene. Or simply dine with a view and play board games. We have poured our hearts into making this place romantic yet practical for families. Enjoy!

Home in Middleton

4.96 out of 5 average rating, 136 reviews

Blue Breeze - Private lakefront w/ Hot Tub

This huge lakeside house is a great experience for all of your friends and family to enjoy all the New Hampshire lakes region has to offer. There is incredible nature all around! Some of our favorites nearby: 11min to a nearby brewery 12min to a great breakfast spot 14min to a farm stand and pick-your-own produce 17min to a nearby winery 21min to Hannafords grocery store 22min to Alton Bay 25min to Wolfeboro 29min to Mt. Major with views of Winnipesaukee 38min to Gunstock mountain for skiing

Cottage in Alton

4.88 out of 5 average rating, 193 reviews

1B Cottage w/kayaks-Lake Winnipesaukee View/Access

Quaint 1 bedroom cottage w/views of Lake Winnipesaukee available year-round. Our deck is literally on Lake Winnipesaukee and a 3 minute walk from the cottage. Here you will be able to enjoy gorgeous views, participate in lake activities such as swimming off our dock, using our kayaks, diving board, etc. The public beach is steps away, along with restaurants, ice cream, water sport rentals, mini-golf & entertainment. Perfect for couples or small family & is pet friendly. Cottage has heat & AC.

Chalet in Bath

4.93 out of 5 average rating, 183 reviews

Mountain Chalet near a Lake

Enjoy this unique A-Frame Chalet in the coveted Mountain Lakes District of NH just 4 miles outside the White Mountains National Forest. Within 30 minutes to Cannon and Loon Ski Resorts and world famous Franconia Notch State Park, this cozy home gives you all the feels of a mountain lifestyle without giving up any comfort. Sun bathe and barbecue out back on the private decks. Dont foget to relax with a unique nature-surrounded experience in the hot tub! A short walk to a beautiful lake view.

Cabin in Conway

4.96 out of 5 average rating, 126 reviews

The Conscious Cabin

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 bath, kitchen, tea/coffee bar, fireplace, outdoor shower, firepit & more. Bask in the restorative magic of cabin living.

Cottage in Middleton

4.97 out of 5 average rating, 152 reviews

Beautiful Lakeside Cottage

Beautiful, quiet and secluded lakeside cottage. Enjoy amazing sunsets on our pristine lake. Swim, kayak, fish or just relax and take in the natural beauty. COVID UPDATE: We know everyone has different levels of concern regarding the virus. Please know that while we feel our sanitation and cleanliness of the Cottage is exceptional, we have doubled our efforts providing multiple cleanings between guests. This is a NON-SMOKING property. We are sorry, but we cannot accommodate pets.

Home in Laconia

4.93 out of 5 average rating, 231 reviews

The Riverhouse Kayaks Pool Table Firepit Downtown

Waterfront location nestled in the heart of Laconia. located on a river connected to Lake Opechee. Kayaks are provided with the home. Walking distance to downtown. A beautiful 7 mile walking trail “wow trail” walking distance from the property. A firepit under the pergola! Access to 2 grills, a large front porch and deck off the queen bedroom with water views. Close to lake Winni, Weirs beach, Bank of NH Pavilion, Gunstock ski and many more local attractions all 10 minutes away.

Home in Wakefield

4.98 out of 5 average rating, 146 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, 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. Book now and get 10% OFF for weekly or longer stays!

Home in Northwood

4.99 out of 5 average rating, 130 reviews

Pleasant Lake Paradise - limited time left to rent

The final countdown to rebuild is on! If you’ve contemplated booking - do it now. We will cease renting summer of 2025 to knock down and rebuild. We love our home away from home...with lake views, two bedrooms, 1.5 baths, and an expansive back deck with hot tub - our peaceful home on Pleasant Lake is sure to please. Boat, swim, kayak, hike, ice fish...or simply relax. In all seasons, this charming home has it all. And, we love your 4 legged friend! Dogs welcome.

Home in Hollis

4.99 out of 5 average rating, 401 reviews

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Cottage in Middleton

4.96 out of 5 average rating, 164 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!

Vacation rentals for every style

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Houses

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Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Lake Winnipesaukee kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Meredith

4.9 out of 5 average rating, 31 reviews

Amazing Cabin w/Hot Tub*King*Outdoor Shower

Home in Bridgton

4.98 out of 5 average rating, 104 reviews

Fish Tales Cabin

Home in Moultonborough

4.95 out of 5 average rating, 61 reviews

Winnipesaukee Beach Access Home

Home in Wakefield

5 out of 5 average rating, 27 reviews

Modern Lakefront Cabin (Pet Friendly, King Beds)

Home in Henniker

4.93 out of 5 average rating, 143 reviews

The Farmhouse at Sweetwater

Home in Waterford

4.84 out of 5 average rating, 233 reviews

McWain pond house (private lake & hot tub)

Home in Shapleigh

4.98 out of 5 average rating, 127 reviews

Secluded Lakehouse/2 private docks*Hottub*big yard

Home in Laconia

5 out of 5 average rating, 25 reviews

Winnipesaukee Lakefront Luxury unit #5 w Hot tub

Cottage rentals with a kayak

Cottage in Conway

4.89 out of 5 average rating, 108 reviews

Cozy Pondside Retreat with direct water access!

Cottage in Epsom

4.97 out of 5 average rating, 214 reviews

Smokey Pines Camp

Cottage in Meredith

4.98 out of 5 average rating, 85 reviews

Pet Friendly Modern Cottage w/ Lake Access

Cottage in Northwood

4.93 out of 5 average rating, 109 reviews

Cottage on the lake! Includes kayaks & rowboat!

Cottage in Thornton

4.94 out of 5 average rating, 145 reviews

Cottage with antique charm view & river HSI Wi-Fi

Cottage in Laconia

4.94 out of 5 average rating, 110 reviews

Completely updated detached cottage/Paugus Bay!

Cottage in Alton

4.95 out of 5 average rating, 62 reviews

Lake Winnipesaukee/9min to Gunstock Mtn. Alton Bay

Cottage in Alton

5 out of 5 average rating, 35 reviews

Windswept Cottage: A Winnipesaukee Waterfront

Cabin rentals with a kayak

Cabin in Hill

5 out of 5 average rating, 42 reviews

Hill Studio

Cabin in Grafton

4.87 out of 5 average rating, 216 reviews

Beautiful Serene Lake/Ski House with central AC

Cabin in Holderness

4.86 out of 5 average rating, 102 reviews

Beautiful private cabin on Big Squam Lake

Cabin in Waterford

4.94 out of 5 average rating, 158 reviews

Lakeside Cabin Nestled in the Pines

Cabin in Harrison

4.99 out of 5 average rating, 121 reviews

Get away at Crystal Lake

Cabin in Bridgton

4.93 out of 5 average rating, 111 reviews

Private cabin w hot tub,skiing,firepit & mountains

Cabin in Wentworth

4.96 out of 5 average rating, 24 reviews

White Mountain retreat | waterfront, amazing views

Cabin in Denmark

4.95 out of 5 average rating, 169 reviews

Maine Lakes-Pleasant Mt-Private Trails

Destinations to explore