Holiday rentals with a kayak in Lake Winnipesaukee

Find and book unique kayak rentals on Airbnb

Top-rated Accommodation with a Kayak in Lake Winnipesaukee

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

%{current} / %{total}1 / 1
Top Guest favourite
A cabin with a spacious deck overlooks a natural setting. The structure features large windows and a bright red umbrella set over a wooden table. Surrounding green trees and shrubs create a serene environment, while a canoe rests nearby on the ground.
Home in Wolfeboro
4.99 out of 5 average rating, 136 reviews

Tranquil Pondside Retreat

Welcome to this clean, bright, airy cabin with floor-to-ceiling windows and stunning views of Sargent's Pond in all seasons. At 62 acres and with just twelve homes, Sargent's Pond is the perfect place for simpler pursuits and peace and quiet. Enjoy two comfortable double bedrooms, a pull-out sofa in the living room, a bathroom with tub, washer, and dryer, a fully equipped kitchen with dishwasher, Wifi, bluetooth stereo system (bring your vinyl!), and Smart TV. Enjoy dining and relaxing on the spacious deck with commanding water views, and for the little ones, swinging and sliding on the swing set. Above the garage is a recreation room with a ping pong table as well as a smashing children's playroom filled with toys, board games, puzzles, and books. Enjoy the TV/ DVD player with a variety of favorite kids' flicks. Perfect for rainy days or down time, this extra living space is sure to please kids and adults alike! Please note that a pack-and-play, toddler mattress, and toddler high chair are available upon request.

Top Guest favourite
An open living area showcases a comfortable gray sofa paired with a coffee table on a textured rug. A practical ladder leads to a loft space. The kitchenette features sleek cabinetry, and natural light fills the room through window treatments.
Cottage in Laconia
4.94 out of 5 average rating, 120 reviews

Completely updated detached cottage/Paugus Bay!

Enjoy your vacation surrounded by all that Lake Winnipesaukee has to offer! You will enjoy beautiful views of Paugus Bay with the most amazing sunsets and fireworks at the Margate right from the front deck! Completely updated unit! Shared Waterfront deck Conveniently located near shopping, hiking and snowmobile trails, the Naswa Beach Bar, Weirs Beach, FunSpot, and the Margate! Perfect location for Laconia's annual BIKE WEEK and just minutes to the Bank of NH Pavilion for some amazing concerts.

Top Guest favourite
Place to stay in Shapleigh
5 out of 5 average rating, 110 reviews

Historic Schoolhouse c1866 / Sauna + Hot Tub + Gym

Winner of Maine Homes Small Space Design Award 2023 We are located on the private 80-acre Shapleigh Pond in the Southern Maine, an hour from Portland and two hours from Boston. Experience a bygone era in this restored Schoolhouse circa 1866 with many original details such as oversized glass-paned windows, wood plank floors, chalkboards, tin ceiling and more. Modern amenities such as fireplace, private hot tub, fire pit, gas BBQ and access to our pool (June-Sept), pond, gym and tennis court.

Top Guest favourite
The studio apartment features a queen size bed with a striped duvet and two large leather chairs. A wooden desk is positioned near a window, while the warm wooden floor adds to the inviting feel of the space.
Apartment in Wakefield
4.98 out of 5 average rating, 113 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.

Superhost
A view from water level shows a bright blue kayak in the foreground, with a forest of tall green trees surrounding a cabin in the background. The cabin features multiple windows that reflect the natural light and scenery.
Cottage in Parsonsfield
4.86 out of 5 average rating, 180 reviews

RiverPine Retreat - Clean & Bright Waterfront Home

Tucked away in a small town, minutes away from the New Hampshire border, located 2 minutes off of rt. 25 (direct route from Portland ME to NH) The ultimate family or couples getaway. Plenty of room in the back yard for any and all yard games, while also enjoying the firepit, "game shed" and 75ft of water frontage where you can swim, fish, or launch your kayaks from the dock into the Ossipee River. Wireless internet is available and reaches the back yard. The 'cabin' has 2 bedrooms.

Guest favourite
The living area features a brown leather sofa paired with a decorative throw, surrounded by large windows that invite natural light. A textured area rug lies beneath a low coffee table, with decorative objects and plants adding a touch of greenery.
Cottage in Gilmanton
4.88 out of 5 average rating, 120 reviews

Gunstock, skiing, hot tub, lake access & fire pit

Welcome to our cozy camp steps away from Sawyer Lake, offering access to 6 beaches. Enjoy our pedal boat and paddle board on the water. The camp features a fully equipped kitchen, grill, large back deck, and a screened-in front porch for relaxation. Minutes away from Bank of NH Pavilion for concerts, Tilton Outlets, Gunstock, NH speedway and Lake Winnipesaukee. Pet-friendly with a relaxing hot tub in the back. Perfect for a peaceful retreat or an adventure-filled getaway in nature!

Superhost
A spacious outdoor seating area is framed by a wooden pergola, with soft lights enhancing the ambiance. A circular fire pit sits at the center, surrounded by a curved sectional couch and additional chairs, offering a comfortable space for gathering near the water.
Home in Laconia
4.92 out of 5 average rating, 262 reviews

Waterfront w Kayaks, Pool table, Pergola, Firepit

Waterfront location nestled in the heart of Laconia. Located on a river connected to Lake Opechee.. Less than 5 minute walk the lake, beaches and downtown. A beautiful 7 mile walking trail “wow trail” right near the property. 2 water facing decks, 1 front porch, 2 grills, fire pit under the pergola, Sundeck on the river, and 2 kayaks are provided with the home. Close to lake Winni, Weirs beach, Bank of NH Pavilion, Gunstock ski and many more local attractions all 10 minutes away

Top Guest favourite
The hot tub is filled with bubbling water, positioned to capture views of the frozen lake and sunset hues in the sky. Surrounding scenery includes a winter landscape, with trees lining the shore and a distant dock. Gentle waves are visible on the water's surface.
Cottage in Middleton
4.96 out of 5 average rating, 214 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!

Top Guest favourite
Home in Wakefield
4.98 out of 5 average rating, 190 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!

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
4.96 out of 5 average rating, 118 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.

Guest favourite
The cottage exterior is surrounded by tall pine trees, providing a natural setting. A pathway leads to the front door, which is flanked by two small potted plants. The view of Pequawket Pond is visible in the background, enhancing the tranquil ambiance.
Cottage in Conway
4.96 out of 5 average rating, 195 reviews

Tiny Lakefront Cottage

Escape to our beautifully redesigned cottage on serene Pequawket Pond, nestled in the heart of New Hampshire's White Mountains. This studio, one of just seven in a private association, offers maximized comfort and space just steps from the water. Enjoy complimentary use of our kayak and two paddleboards, or simply unwind on the patio with grill, soaking in the breathtaking pond views. Your perfect lakeside retreat awaits!.

Guest favourite
A log cabin surrounded by trees is situated near the shoreline of the Ossipee River. A wooden deck extends from the cabin, and a red tandem kayak is positioned on a small dock, creating an inviting space for outdoor activities.
Cabin in Parsonsfield
4.95 out of 5 average rating, 253 reviews

Riverfront cabin between Portland & White Mtns.

Look out onto the always-changing Ossipee River from this cute little log cabin. Use our tandem kayak, or fish and swim from our dock. In the winter months, ride your snowmobile right from the driveway, take a brewery tour in Portland, head to the White Mountains, or just watch the river go by. Cornish, Maine is just 12 minutes away and has plenty of dining and shopping opportunities.

Popular amenities for Lake Winnipesaukee kayak rentals

Destinations to explore