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Vacation rentals with a kayak in Lake Winnisquam

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Top-rated kayak rentals in Lake Winnisquam

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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Guest favorite
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

Outdoor spacesValueWalkability

4.94 out of 5 average rating, 124 reviews
Guest favorite
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.

LocationOutdoor spacesIndoor spaces

4.94 out of 5 average rating, 53 reviews
Top guest favorite
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

Take it easy at this unique and tranquil getaway. This former Architect’s studio has been set up as a one bedroom guest house. It is a wonderful spot to relax and snuggle up next to the fire with your favorite book, beverage, or a special someone. The studio is very private with only the trees or maybe a visiting moose to see in. We are 30 min. to Ragged Mountain and Newfound Lake. We have a friendly dog and preapproved well-behaved pets are welcome. An all-wheel drive car is needed in winter.

Outdoor spacesValueHospitality

4.98 out of 5 average rating, 116 reviews
Top guest favorite
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.

LocationOutdoor spacesLaundry

4.94 out of 5 average rating, 88 reviews
Top guest favorite
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 spacesLaundry

4.99 out of 5 average rating, 337 reviews
Top guest favorite
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.

ValueLocationHeating

4.96 out of 5 average rating, 201 reviews
Guest favorite
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).

Outdoor spacesValueBeach

4.95 out of 5 average rating, 276 reviews
Guest favorite
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.

Outdoor spacesLocationAmenities

4.87 out of 5 average rating, 103 reviews
Top guest favorite
Cottage in Tilton

Big Pine Lakefront Cottage, Dock, Kayaks & Firepit

Welcome to Big Pine Cottage. Your Summer or Winter Cabin Retreat Awaits You! Come relax and gather around the fire pit. Catch fish from the water’s edge. 100 feet of water frontage on a sandy bottom lake provides a great space to swim and relax. Explore the lake on our 4 person commercial grade peddle boat. We have 2 sit in style kayaks. Only a 5 minute drive from the Lake Estate on Winnisquam! Enjoy a peaceful and more tranquil experience when traveling for weddings and events!

Outdoor spacesLocationAccess

4.98 out of 5 average rating, 43 reviews
Top guest favorite
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!

LocationValueCheck-in

4.98 out of 5 average rating, 210 reviews
Top guest favorite
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.

ValueOutdoor spacesLaundry

4.96 out of 5 average rating, 136 reviews
Guest favorite
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 spacesValueLaundry

4.95 out of 5 average rating, 139 reviews

Popular amenities for Lake Winnisquam kayak rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a kayak

Guest favorite
Home in Tilton

Lakefront Getaway w/ Firepit & Mountain Views

LocationOutdoor spacesKitchen

4.93 out of 5 average rating, 15 reviews
Top guest favorite
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

Outdoor spacesLocationGrill

4.99 out of 5 average rating, 70 reviews
Top guest favorite
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

LocationOutdoor spacesCheckout

4.97 out of 5 average rating, 68 reviews
Top guest favorite
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

LocationValueHiking

4.99 out of 5 average rating, 97 reviews
Top guest favorite
Home in Center Harbor

Hidden Kids Room | Kayaks | Fire Pit | Epic views

LocationOutdoor spacesWifi

4.98 out of 5 average rating, 48 reviews
Top guest favorite
Home in New Durham

Waterfront Chalk Pond | Fireplace | Kayaks

Outdoor spacesLocationFamily

5.0 out of 5 average rating, 27 reviews
Top guest favorite
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

Outdoor spacesValueHospitality

4.98 out of 5 average rating, 48 reviews
Top guest favorite
Home in Gilford

Snowy Acres

LocationHospitalityCleanliness

5.0 out of 5 average rating, 9 reviews

Cottage rentals with a kayak

Guest favorite
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!

LocationValueSleep quality

4.94 out of 5 average rating, 125 reviews
Guest favorite
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

ValueLocationHeating

4.96 out of 5 average rating, 241 reviews
Guest favorite
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!

Outdoor spacesLocationLayout

4.88 out of 5 average rating, 133 reviews
Top guest favorite
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

ValueOutdoor spacesHospitality

4.93 out of 5 average rating, 163 reviews
Top guest favorite
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

LocationOutdoor spacesCleanliness

4.97 out of 5 average rating, 239 reviews
Top guest favorite
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.

Outdoor spacesLocationWalkability

4.98 out of 5 average rating, 122 reviews
Guest favorite
A scenic aerial view showcases the lakeside property surrounded by lush greenery. A well-manicured lawn leads to the water's edge, where a small rowboat rests. Adjacent seating areas invite relaxation while vibrant trees add color to the landscape.
Cottage in Springfield

Quaint lakefront; firepit, boat, kayaks, hammock

LocationOutdoor spacesGrill

4.88 out of 5 average rating, 155 reviews
Top guest favorite
Cottage in Thornton

Charming Mountain View River Cottage w/ Pvt. Trail

Outdoor spacesLocationParking

4.96 out of 5 average rating, 194 reviews

Cabin rentals with a kayak

Guest favorite
Cabin in Warren

Breezy Moose - A Frame Cabin/ Pet friendly

ValueOutdoor spacesSleep quality

4.94 out of 5 average rating, 158 reviews
Top guest favorite
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 spacesWifi

4.96 out of 5 average rating, 147 reviews
Top guest favorite
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

ValueLocationHiking

4.97 out of 5 average rating, 181 reviews
Top guest favorite
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.

Outdoor spacesLocationFamily

4.89 out of 5 average rating, 100 reviews
Guest favorite
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 spacesHeating

4.87 out of 5 average rating, 253 reviews
Guest favorite
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

ValueOutdoor spacesAccess

4.9 out of 5 average rating, 181 reviews
Guest favorite
A cozy sleeping space features a queen bed adorned with a soft, striped blanket and decorative pillow. A small nightstand and a mini-fridge are nearby. Natural light filters through sheer curtains, illuminating the wooden walls and adding to the cabin's warm atmosphere.
Cabin in Henniker

The Glamp Camp at Sweetwater

Outdoor spacesLocationCondition

4.94 out of 5 average rating, 155 reviews
Guest favorite
A charming cabin exterior is showcased, featuring a wooden facade with large windows framed by greenery. A small patio area with a picnic table is set in front, surrounded by seasonal foliage displaying autumn colors.
Cabin in Holderness

Beautiful private cabin on Big Squam Lake

ValueOutdoor spacesComfort

4.86 out of 5 average rating, 112 reviews

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