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Holiday rentals with a kayak in Lake Winnipesaukee

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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.

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Guest favourite
An expansive wooden deck provides a welcoming space for relaxation, featuring multiple chairs and a table. A large umbrella offers shade, while the lake and trees are visible in the background, showcasing the natural surroundings and unobstructed views.
Home in Tuftonboro

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
Top Guest favourite
A hobbit house is nestled among lush green trees, with a sloping earth-covered roof adorned with grass and ferns. The rounded front features a large window framed in white, complemented by a natural stone border, emphasizing the home's connection with its woodland surroundings.
Earthen home in Sanford

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
Top Guest favourite
A family lake house is positioned over the water, surrounded by lush trees. The two-story structure features multiple decks, providing space for outdoor activities. Colorful kayaks and paddleboards are visible along the dock, reflecting a peaceful lakeside ambiance under a partly cloudy sky.
Cottage in Alton

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, 88 reviews
Top Guest favourite
Cabin in Alexandria

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
Top Guest favourite
A modern two-story home is set amidst a wooded area, featuring a spacious outdoor seating arrangement with a picnic table and various chairs. A fire pit and grill are present, with the soft glow of twilight highlighting the inviting exterior.
Cottage in Acton

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, 187 reviews
Top Guest favourite
A serene view of Mirror Lake presents a tranquil morning scene, where mist rises gently from the water's surface. Two chairs are positioned in the foreground, inviting relaxation. Soft sunlight glimmers on the lake, enhancing the peaceful ambiance of the natural surroundings.
Home in Tuftonboro

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
Top Guest favourite
A warm and inviting living area showcases a stone fireplace framed by soft lighting. Two plush armchairs are positioned near a wooden coffee table. A cozy sofa adorned with a colorful blanket complements the wooden beams and walls, creating a tranquil atmosphere.
Cabin in Conway

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.

4.96 out of 5 average rating, 201 reviews
Guest favourite
Cabin in Barnstead

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, 276 reviews
Top Guest favourite
A serene lakeside view is presented, featuring a well-maintained garden with colorful flowers and lush greenery. Smooth stones create a path leading towards the calm waters of Sunrise Lake. The dock and surrounding trees are visible under a bright blue sky with scattered clouds.
Cottage in Middleton

☀ 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!

4.97 out of 5 average rating, 239 reviews
Top Guest favourite
Home in Wakefield

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
Top Guest favourite
An outdoor dining area features a rectangular table surrounded by six chairs, set against the backdrop of a serene waterfront. The golden sunset casts warm hues over the lake, while red umbrellas provide shade. The cozy cottage is positioned at the water's edge, surrounded by lush greenery.
Home in Laconia

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 reviews
Top Guest favourite
A spacious master bedroom features warm wooden walls and ceiling beams, creating a cozy ambiance. A plush bed is positioned in front of a stone fireplace. Large glass doors invite natural light and provide views of the outdoor space, enhancing the overall serenity.
Guest suite

A luxury log apartment located on the Saco River

This exquisite log apartment offers a one of a kind luxury experience with a private master bedroom including a gas stone fire place, king bed with exquisite bedding and a balcony which overlooks a 140’ private beach on the Saco River. Also included is a fully equipped designer kitchen/living area with a queen sofa bed, a full spa-like bathroom with a steam shower, Kohler bidet, and soaking tub.

5.0 out of 5 average rating, 217 reviews

Popular amenities for Lake Winnipesaukee kayak rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Holiday House Rentals with a Kayak

Guest favourite
A hot tub sits on a wooden deck, overlooking a serene lakeside view. Lush greenery surrounds the area, with clear blue skies overhead and a sandy beach visible in the background. The relaxing setting invites peaceful outdoor enjoyment.
Home in Wakefield

Lake Front Log Cabin · Hot Tub · Arcade · Fire Pit

4.83 out of 5 average rating, 120 reviews
Top Guest favourite
Red Adirondack chairs surround a fire pit on sandy ground, facing a serene lakeside view. Towering trees provide shade, and the calm water reflects the clear blue sky, creating an inviting atmosphere for gatherings and relaxation.
Home in Wolfeboro

Lakeside Getaway - Lake Access/PrivateDock/Firepit

4.97 out of 5 average rating, 29 reviews
Top Guest favourite
A private dock extends into a serene lake, surrounded by lush greenery and trees. Four adirondack chairs are arranged on the dock, facing calm waters reflecting the sky. A person stands with arms outstretched, enjoying the peaceful lakefront landscape.
Home in Meredith

New Home Discount! Lakefront|Dock|Fireplace|XBox

4.95 out of 5 average rating, 44 reviews
Top Guest favourite
Home in New Durham

Waterfront Chalk Pond | Fireplace | Kayaks

5.0 out of 5 average rating, 27 reviews
Top Guest favourite
A cozy living space features a high, vaulted wooden ceiling with large triangular windows showcasing lake views. Two hanging chairs are positioned beside a plush sofa, and a coffee table sits on an area rug, enhancing the inviting atmosphere.
Home in Wolfeboro

Luxury Lakehouse| Sunsets| Cen. Air| Private Dock

4.99 out of 5 average rating, 81 reviews
Top Guest favourite
A modern house with a sloped roof is surrounded by greenery. A spacious backyard features several teal chairs arranged around a fire pit, inviting relaxation. A white picket fence encloses the area, while a two-car garage is visible in the back.
Home in Meredith

Lovely home, across from lake, walk to Meredith

4.97 out of 5 average rating, 68 reviews
Top Guest favourite
An aerial view captures a spacious home nestled among tall trees on the edge of Balch Lake. Two private docks are visible along the shoreline, complemented by a grassy area that leads to a sandy beach. The calm water reflects the surrounding greenery.
Home in Newfield

Peaceful 4 bedroom lakehouse retreat

4.98 out of 5 average rating, 45 reviews
Top Guest favourite
Home in Wakefield

Fall Lakefront Luxe I Cozy I Bonfire I Hot Tub

5.0 out of 5 average rating, 30 reviews

Cottages with a kayak

Top Guest favourite
The lake-front cottage is surrounded by trees and features a spacious deck with seating. Colorful adirondack chairs are arranged in a circular pattern near a stone-bordered landscaping area, adding inviting outdoor space for relaxation. A screen porch is visible on the side of the house.
Cottage in Middleton

Lovely cottage on Sunrise Lake, Middleton, NH.

4.98 out of 5 average rating, 122 reviews
Top Guest favourite
A cozy cottage exterior is shown, featuring light-colored siding and a welcoming wooden entrance deck. Surrounding greenery enhances the tranquil setting, while a driveway leads to the property. The serene lake is visible in the background, surrounded by trees, inviting a peaceful retreat.
Cottage in Middleton

Beautiful Lakeside Cottage

4.97 out of 5 average rating, 184 reviews
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

RiverPine Retreat - Clean & Bright Waterfront Home

4.84 out of 5 average rating, 197 reviews
Top Guest favourite
The open-concept living area features a sleek gray sofa with decorative pillows and a spacious wooden dining table. Natural light floods the room through large windows, while a wall-mounted TV enhances the entertainment options. The warm wooden ceiling adds a cozy touch.
Cottage in Wakefield

Gorgeous Romantic Lakefront Getaway

4.99 out of 5 average rating, 122 reviews
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

Completely updated detached cottage/Paugus Bay!

4.94 out of 5 average rating, 125 reviews
Top Guest favourite
A single-story cottage is nestled among trees, featuring a light yellow exterior with dark shutters. The well-kept front yard showcases a carpet of fallen leaves, and a small deck is visible to the right, enhancing access to the inviting outdoor space.
Cottage in Alton

“Stay Awhile in the Lake's Region”

4.99 out of 5 average rating, 145 reviews
Guest favourite
Two individuals are seated in white chairs on a stone patio, positioned around a crackling fire. The cottage is visible in the background, showcasing large windows and a rustic wooden deck. Lush greenery frames the area, contributing to the natural surroundings.
Cottage in Epsom

Smokey Pines Camp

4.96 out of 5 average rating, 241 reviews
Top Guest favourite
A vibrant blue cottage sits nestled among greenery, with a welcoming entrance and an American flag displayed. A dock with two kayaks rests at the water's edge, reflecting the serene lake. A patio area is visible on the upper deck, inviting relaxation.
Cottage in Northwood

Waterfront Cottage Private Dock | Kayaks | Rowboat

4.93 out of 5 average rating, 163 reviews

Cabin rentals with a kayak

Top Guest favourite
A pathway lined with vibrant pink rhododendron bushes leads to a distinctive metal-clad entrance. The structure features a sloped roof with skylights, surrounded by greenery, providing a welcoming approach to the private studio.
Cabin in Hill

Hill Studio

4.98 out of 5 average rating, 116 reviews
Superhost
A hot tub bubbles gently, surrounded by towering trees and a serene view of Moose Pond. The water reflects the clear blue sky and is framed by a tranquil landscape, creating a peaceful atmosphere for relaxation.
Cabin in Bridgton

Waterfront,Hot tub,Private dock,Freshly renovated

4.82 out of 5 average rating, 192 reviews
Guest favourite
Cabin in Warren

Breezy Moose - A Frame Cabin/ Pet friendly

4.94 out of 5 average rating, 158 reviews
Guest favourite
A spacious outdoor patio is surrounded by a stone path and colorful garden beds. Multiple lounge chairs are arranged around a stone fire pit, creating a cozy gathering space. Large windows offer views of the surrounding trees and provide natural light to the cabin.
Cabin in Madison

Bear Cabin

4.9 out of 5 average rating, 181 reviews
Guest favourite
A spacious living area is adorned with warm wooden paneling and large windows that overlook the natural surroundings. Comfortable seating includes a large sectional sofa and a dark coffee table, complemented by lamps that provide soft lighting. A television is positioned on a media unit against the wall.
Cabin in Denmark

Cabin w/ Lake Access, Hot Tub, Kayaks, + Firepit!

4.96 out of 5 average rating, 188 reviews
Top Guest favourite
A cozy living area features a comfortable sofa and a wooden table beneath a rustic wooden ceiling with exposed beams. A wooden ladder with handrails leads to a loft space above, adding charm and functionality to the cabin's interior.
Cabin in Andover

Little House on the Lake in the Forest

4.96 out of 5 average rating, 147 reviews
Top Guest favourite
The exterior of the log cabin features a prominent stone chimney and large windows reflecting the snowy landscape. Two chairs, covered in snow, are placed near the entrance, evoking a cozy atmosphere. The surrounding trees are blanketed in white.
Cabin in Barrington

Adorable log cabin on the lake.

4.89 out of 5 average rating, 100 reviews
Guest favourite
An open living area features large windows overlooking the lake, bringing in natural light. Wood ceiling beams enhance the spaciousness. A comfortable sectional sofa faces a mounted television, and a wooden chair adds to the seating. The warm wood flooring complements the tranquil atmosphere.
Cabin in Grafton

Beautiful Serene Lake/Ski House with central AC

4.87 out of 5 average rating, 253 reviews

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