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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

ValueLocationCleanliness

4.94 out of 5 average rating, 123 reviews
Guest favourite
Home in Moultonborough

Camp Oscar Waterfront Lake Winnipesaukee

Experience the true meaning of Lake Life at Camp Oscar. This classic Lake Winnipesaukee waterfront retreat in Moultonborough offers the perfect setting for a memorable Lakes Region getaway. Featuring 4 bedrooms, 1.5 baths, warm wood finishes throughout, a private dock, and a walk-out sandy beach, Camp Oscar is ideal for swimming, boating, fishing, and relaxing by the water. Enjoy beautiful lake views, timeless camp charm, and everything you need to create lasting memories with family and friends

LocationOutdoor spacesFamily

5.0 out of 5 average rating, 8 reviews
Top Guest favourite
A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.
Treehouse in Sanford

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.

ValueOutdoor spacesEV charging

4.91 out of 5 average rating, 601 reviews
Guest favourite
Home in Wolfeboro

Gram's House

Enjoy easy access to town from this historic home. Relax on the deck overlooking Wolfeboro Bay. Enjoy a swim whenever you want. There are 4-season activities in the area: bike, hiking and ski trails close by. Private beach, raft (no dock), canoe/kayaks, and beach toys. Great gathering place: our family has enjoyed many special events here! HOWEVER, if you are looking for a place to have loud parties, this is not for you. This rental is in a neighborhood and we respect our neighbors.

LocationOutdoor spacesComfort

4.83 out of 5 average rating, 18 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 spacesValueDecor

4.94 out of 5 average rating, 85 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!

LocationValueAccess

4.99 out of 5 average rating, 184 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.

LocationValueDecor

4.98 out of 5 average rating, 45 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).

Outdoor spacesValueCheckout

4.95 out of 5 average rating, 272 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

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.

Outdoor spacesLocationAccess

4.97 out of 5 average rating, 181 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!

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!

LocationOutdoor spacesComfort

4.98 out of 5 average rating, 210 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

Beautiful four bedroom two bath home located on Balch Lake in West Newfield Maine. Two private docks and your own boat launch. Sandy beach area on the south side of the house receives lots of sunshine. Take out kayaks or pedal boat to explore Balch Lake! Updated kitchen and a magnificent view of the lake from the living room. Relax in the shade under 2 motor canopies on the deck off of the master bedroom. Enjoy a barbeque and go for a swim at this hidden gem.

Outdoor spacesLocationBarbecue

4.98 out of 5 average rating, 44 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

Escape to this cozy lakeside retreat with direct access to Crescent Lake - perfect for swimming, kayaking, or simply enjoying the view. Bring your own boat and take advantage of the private dock, offering effortless access to the water for fishing, cruising, or sunset rides. In the evening, gather around the fire pit and unwind under the stars.​ This house is ideal for couples, families, or groups seeking comfort, nature, and connection.

Outdoor spacesLocationAmenities

4.96 out of 5 average rating, 26 reviews

Popular amenities for Lake Winnipesaukee kayak rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Holiday House Rentals with a Kayak

Superhost
The two-story lakeside house features large windows and a spacious deck with seating. A private dock is visible in front, with lounge chairs arranged on the sandy beach nearby. Lush greenery surrounds the property, creating a serene outdoor space.
Home in Middleton

Blue Breeze - Private lakefront w/ Hot Tub

ValueOutdoor spacesAccuracy

4.88 out of 5 average rating, 226 reviews
Top Guest favourite
The exterior of the farmhouse features a well-maintained white siding facade and a welcoming yellow front door. A neatly landscaped yard is present, showcasing a mix of greenery and colorful flowers. Stone pathways and a low stone wall add rustic charm to the serene setting.
Home in Hebron

Hebron Historic Farmhouse

Outdoor spacesValueCheckout

4.98 out of 5 average rating, 299 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

LocationOutdoor spacesView

4.99 out of 5 average rating, 75 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

Outdoor spacesValueBeach

4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Wakefield

Luxury Lake House +Hot Tub! Waterfront Magic in NH

Outdoor spacesLocationGetting around

5.0 out of 5 average rating, 29 reviews
Top Guest favourite
An outdoor living area features a fire table surrounded by comfortable seating. A large patio umbrella provides shade, while an outdoor kitchen and grill are visible in the background. Lush trees surround the space, creating a serene atmosphere for gatherings.
Home in Moultonborough

Eagles Landing with Hot Tub, Boat Slip @ Braun Bay

LocationOutdoor spacesDecor

4.98 out of 5 average rating, 40 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

Outdoor spacesLocationHiking

4.99 out of 5 average rating, 96 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

Outdoor spacesLocationRiver

4.98 out of 5 average rating, 47 reviews

Cottages with a kayak

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

ValueOutdoor spacesCheck-in

4.99 out of 5 average rating, 118 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

LocationValueAccess

4.97 out of 5 average rating, 236 reviews
Top Guest favourite
A quaint cottage exterior is depicted with a backdrop of vibrant fall foliage. The structure features light gray siding and a welcoming front door, while the calm waters of Lake Winnipesaukee are visible in the background.
Cottage in Alton

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

ValueOutdoor spacesSleep quality

4.89 out of 5 average rating, 238 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

Outdoor spacesValueAccess

4.84 out of 5 average rating, 194 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

Outdoor spacesLocationAccuracy

4.96 out of 5 average rating, 134 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”

Outdoor spacesValueSkiing

4.99 out of 5 average rating, 145 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

Outdoor spacesLocationGetting around

4.94 out of 5 average rating, 159 reviews
Top Guest favourite
Cottage in Thornton

Charming Mountain View River Cottage w/ Pvt. Trail

ValueOutdoor spacesCheck-in

4.96 out of 5 average rating, 192 reviews

Cabin rentals with a kayak

Top Guest favourite
Cabin in Alexandria

Mountain Lodge with Private Sauna

LocationValueIndoor spaces

4.98 out of 5 average rating, 332 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

Outdoor spacesValueSkiing

4.82 out of 5 average rating, 190 reviews
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

Outdoor spacesLocationBiking

4.98 out of 5 average rating, 115 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

ValueLocationTV

4.96 out of 5 average rating, 201 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

Outdoor spacesValueFamily

4.9 out of 5 average rating, 180 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

LocationValueBeach

4.88 out of 5 average rating, 251 reviews
Top Guest favourite
Cabin in Warren

Breezy Moose - A Frame Cabin/ Pet friendly

ValueLocationNearby

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 spacesWi-Fi

4.96 out of 5 average rating, 144 reviews

Destinations to explore