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Holiday rentals with a kayak in Lake Winnisquam

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Top-rated Accommodation with a Kayak in Lake Winnisquam

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

LocationValueBeach

4.94 out of 5 average rating, 122 reviews
Guest favourite
Home in Belmont

Waterfront FamFriendly Lakehouse -Sauna & New Dock

Welcome to The Zen Den of New Hampshire! This waterfront property has 3 bedrooms, 2 bathrooms and enough sleeping arrangements for up to 12 guests to enjoy the impressive 2,000 sq ft of living space on 2 floors. An ideal accommodation choice for families and close friends looking for the ultimate Lakes Region experience! You’ll feel right at home from the moment you step inside. Enjoy a beautiful interior with high ceilings, comfortable furnishings, Wifi & smart TV's, and gorgeous lake views.

Outdoor spacesLocationHospitality

4.94 out of 5 average rating, 53 reviews
Top Guest favourite
The spacious lakeside home is surrounded by lush trees, with a private dock extending into the water. A large deck provides outdoor seating, while a small sandy beach area invites relaxation. Sunlight filters through the greenery, creating a serene atmosphere for guests.
Home in Belmont

Lakefront Bliss|Private Dock & Year-Round Retreat

Escape to our serene Sargent Lake retreat, where year-round adventures and relaxation await.Enjoy fishing,swimming,and boating in summer or cozy up after a day of skiing, snowmobiling, or hiking in winter.Nestled in the heart of Belmont,NH,this spacious getaway features a private dock,stunning lake views,and plenty of space for family fun. Perfect for nature lovers,families,and those seeking a peaceful escape,our home is your ideal destination to create lasting lakefront memories in every season

ValueLocationAir conditioning

5.0 out of 5 average rating, 67 reviews
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.

Outdoor spacesValueKitchen

4.94 out of 5 average rating, 85 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.

LocationOutdoor spacesComfort

4.98 out of 5 average rating, 332 reviews
Top 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).

ValueOutdoor spacesAmenities

4.95 out of 5 average rating, 272 reviews
Guest favourite
An outdoor patio area overlooks the serene waterfront, featuring a shaded seating arrangement with plush cushions and a coffee table. A gas grill is positioned nearby, accompanied by an umbrella providing shade. Lush greenery surrounds the space, enhancing the tranquil atmosphere.
Cottage in Belmont

Little Cottage - Private Lakefront

This lakefront cottage has it all! Charming 2-bedroom, 1-bath retreat in New Hampshire's scenic Lakes Region. Enjoy a year-round outdoor adventure or peaceful lakeside relaxation. 150ft of private waterfront to swim, kayak, or fish, a spacious yard with patios, grill, and a fire table. Nearby hiking trails, Gunstock Mountain, Highland Mountain Bike Park, and Lake Winnipesaukee. Just a short drive to top skiing resorts, restaurants, shopping, and more, your ideal base for every season.

Outdoor spacesLocationQuiet

4.87 out of 5 average rating, 70 reviews
Guest favourite
A spacious porch features several white rocking chairs arranged to overlook the serene lake. Lush green trees are visible in the background, creating a peaceful outdoor setting. The wooden floor complements the inviting area, providing plenty of space for relaxation.
Home in Tilton

Winnisquam Lake House

Welcome to the beautiful Winnisquam lake house. The house has a beautiful view of the lake from the porch, a few steps down to a beach with clean shallow water, soft sandy bottom for swimming and kayaking, Adirondack chairs on the deck. This home has everything you need to enjoy the lake during the summer, ski slopes in the winter. Completely remodeled kitchen, a huge living room, 4 spacious bedrooms, total of 2000sqft living space. Enjoy kayak, boats, hiking skiing biking, and more.

LocationOutdoor spacesIndoor spaces

4.87 out of 5 average rating, 102 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

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.

Outdoor spacesLocationBathroom

4.97 out of 5 average rating, 63 reviews
Top Guest favourite
A sandy beach area is depicted where four individuals sit along the water's edge, engaging with the lake. A small boat is moored nearby, and a floating platform is visible on the water's surface. Gentle waves lap at the shore, creating a serene atmosphere.
Cottage in Gilmanton

Private Beach, Lake Front, Family Friendly Cottage

Our clean private sandy beach, with a gentle slope is perfect for all swimmers. Sawyer Lake is a fun community. Enjoy our fun lakefront cottage with the perfect layout. 15 min. to Gunstock, Weirs Beach & Tilton Outlets • Kids will want to stay downstairs with a walkout, board games, TV, and 2 gaming systems [XBox 360° & Wii] with games. • Adults relax in peace upstairs with 2 private bedrooms, living area, & wood burning fireplace. Ask about weekends.

ValueLocationAccess

4.96 out of 5 average rating, 134 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

Outdoor spacesLocationQuiet

4.99 out of 5 average rating, 96 reviews
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

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.

Outdoor spacesLocationKitchen

4.95 out of 5 average rating, 137 reviews

Popular amenities for Lake Winnisquam kayak rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Holiday House Rentals with a Kayak

Superhost
A spacious farmhouse is set among lush greenery, featuring a well-maintained lawn. A combination of porches and seating areas, including red adirondack chairs, are visible. The exterior showcases a charming white facade with a star accent, surrounded by tall trees.
Home in Ashland

Squam Lake Farmhouse, Beach Access, Winter Skiing

Outdoor spacesLocationPool

4.86 out of 5 average rating, 213 reviews
Top Guest favourite
A serene view of the calm lake reflects the blue sky and surrounding pine trees, creating a peaceful atmosphere. A wooden dock extends into the water, offering a space for activities and relaxation.
Home in Wakefield

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!

ValueLocationAmenities

4.98 out of 5 average rating, 210 reviews
Guest favourite
Home in Wolfeboro

Gram's House

LocationOutdoor spacesComfort

4.83 out of 5 average rating, 18 reviews
Guest favourite
Home in Moultonborough

Camp Oscar Waterfront Lake Winnipesaukee

LocationOutdoor spacesHospitality

5.0 out of 5 average rating, 8 reviews
Top Guest favourite
An aerial view showcases The Riverview Haven nestled amidst vibrant autumn foliage along the edge of Lake Waukewan. The red structure is surrounded by lush trees and serene water, reflecting the colorful landscape under a clear sky.
Home in Center Harbor

kids hidden room, firepit, Kayaks/Canoes, ev

LocationOutdoor spacesKitchen

4.98 out of 5 average rating, 47 reviews
Guest favourite
The log home is surrounded by lush greenery and large boulders, featuring a striking A-frame design with expansive glass windows. A spacious deck wraps around the structure, providing a sense of harmony with the natural landscape and ample outdoor space.
Home in Meredith

"The Cove" Waterfront Home on Lake Winnipesaukee

LocationOutdoor spacesBackyard

4.88 out of 5 average rating, 89 reviews
Top Guest favourite
Home in Gilford

Snowy Acres

LocationCheckoutIndoor spaces

5.0 out of 5 average rating, 8 reviews
Top Guest favourite
A scenic view showcases a tranquil waterfront area featuring a new aluminum dock extending into Locke Lake. Colorful kayaks are positioned on the grassy shore, while a spacious deck is surrounded by outdoor seating arrangements. The calm water reflects the lush greenery of the surroundings.
Home in Barnstead

Lucky Duck Lodge - Waterfront home on Locke Lake

Outdoor spacesLocationCheck-in

5.0 out of 5 average rating, 71 reviews

Cottages with a kayak

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

LocationOutdoor spacesSleep quality

4.97 out of 5 average rating, 181 reviews
Top Guest favourite
A serene lakeside scene features a plush chair by the water, where a golden retriever is comfortably resting. Lush greenery surrounds the lake, and a kayak is seen moored nearby, adding to the tranquil atmosphere.
Cottage in Newbury

Large Private Lake House

LocationValueAir conditioning

4.95 out of 5 average rating, 252 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

LocationValueWalkability

4.96 out of 5 average rating, 237 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

ValueOutdoor spacesWi-Fi

4.99 out of 5 average rating, 184 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

LocationValueAccess

4.94 out of 5 average rating, 159 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!

ValueOutdoor spacesGetting around

4.94 out of 5 average rating, 124 reviews
Guest favourite
The exterior of the camp is surrounded by trees, featuring a screened-in porch and large windows. A flag is displayed on the front, and gravel paths lead to the entrance. The building is designed to blend with the natural landscape.
Cottage in Gilmanton

Cozy cottage near Gilford, lake access & hot tub!

LocationOutdoor spacesHeating

4.88 out of 5 average rating, 132 reviews
Top Guest favourite
Cottage in Thornton

Charming Mountain View River Cottage w/ Pvt. Trail

ValueLocationBackyard

4.96 out of 5 average rating, 192 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

LocationOutdoor spacesAmenities

4.98 out of 5 average rating, 115 reviews
Guest favourite
A spacious wooden deck overlooks the serene waters of Bradley Lake, surrounded by lush greenery. Two white adirondack chairs are positioned thoughtfully on the deck, providing comfortable seating to enjoy the tranquil views and fresh air.
Cabin in Andover

Sunny Lakeside Cabin + Dock and Boats

LocationOutdoor spacesQuiet

4.88 out of 5 average rating, 104 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

Outdoor spacesLocationSkiing

4.96 out of 5 average rating, 201 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

ValueOutdoor spacesGetting around

4.88 out of 5 average rating, 251 reviews
Top Guest favourite
A two-story cabin is surrounded by lush greenery and located by the water's edge. The exterior features large windows and a deck adorned with decorative railings. Boats can be seen moored alongside the rocky shore, reflecting the calm water of Perkins Pond.
Cabin in Sunapee

Cozy waterfront cabin Perkins Pond

ValueOutdoor spacesAir conditioning

4.97 out of 5 average rating, 138 reviews
Top Guest favourite
Cabin in Warren

Breezy Moose - A Frame Cabin/ Pet friendly

ValueLocationDecor

4.94 out of 5 average rating, 155 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

LocationOutdoor spacesAccess

4.96 out of 5 average rating, 144 reviews
Top Guest favourite
The cabin features a wooden exterior with large windows and a sloped roof, surrounded by natural greenery. A front porch extends from the building, providing access through stairs. The entrance is framed by a welcoming entryway and a small outdoor area.
Cabin in Henniker

The SugarShack at Sweetwater

Outdoor spacesLocationAccess

4.97 out of 5 average rating, 179 reviews

Destinations to explore