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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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, 137 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
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
4.91 out of 5 average rating, 122 reviews

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.

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
4.99 out of 5 average rating, 108 reviews

Gorgeous Romantic Lakefront Getaway

Beautiful, 170 feet of waterfront Carriage House with a lovely sandy beach for a relaxing vacation in the Lakes Region of New Hampshire. Very close to the White Mountain National Forest, Kancamagus Highway, and several Ski Resorts. Within 45 minutes to the beaches of Maine and the Seacoast of New Hampshire. Our Carriage House is 1.5 hours from Boston and 2 hours from Worcester, MA. The Carriage House was built in 2021 with top-line finishes, fixtures, and furnishings for a romantic getaway.

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.

Guest favourite
A private dock extends over the calm waters, featuring two red Adirondack chairs facing the serene lake. An American flag waves gently on a pole, surrounded by vibrant autumn foliage reflected in the water.
Cabin in Tuftonboro
4.96 out of 5 average rating, 25 reviews

Bear Paw

The Pow Wow Lodge property has been a family run business colony since 1963. These vintage cottages offers guests the perfect vacation spot to relax, unwind and enjoy all the area has to offer. We have 1 bedroom with a double bed, one bedroom with 2 singles and a single bed on the porch. Experience the beauty, nature and quietness of this pristine lake with your own private dock along with breathtaking mountain views. Spend your time swimming, boating, fishing, paddle boarding and relaxing

Top Guest favourite
A spacious deck features several black reclining chairs arranged around a white table. Vivid autumn foliage is visible in the background, along with distant mountains and a clear blue sky. The scene invites relaxation in a serene outdoor setting.
Home in Orford
4.98 out of 5 average rating, 159 reviews

Romantic Mountain Getaway

Come enjoy the peacefulness that only living in the mountains can give you, without letting go of every day luxuries. Our place is ideal for romantic getaways with its beautiful and private setting! Lots of things to do in the area as well. The serene Indian Pond is located just down the road and it is ideal for swimming & kayaking in the summer and snowshoeing in the winter. Hike Mt. Moosilauke and enjoy stunning views, or hike Mt. Cube or Smarts Mountain for smaller fun family adventures.

Top Guest favourite
Cabin in Barnstead
4.95 out of 5 average rating, 269 reviews

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).

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
4.97 out of 5 average rating, 173 reviews

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.

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, 264 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

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
4.95 out of 5 average rating, 113 reviews

20 Mile Bay - Tuftonboro - Lake View

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. The property is surrounded by conservation land. The Chandler Wild Park Trail has an entrance right in front of the property. It is perfect for hiking, snow shoeing, cross country skiing, and walking.

Top Guest favourite
Cabin in Alexandria
4.98 out of 5 average rating, 103 reviews

Modern Rustic Cabin with Sauna near Lake and Hike

Escape to Black Dog Cabin, less than 2 hours from Boston: - Gather under the stars by the fire pit - Relax or grill on the huge back deck & sauna - Enjoy our pet-friendly working homestead - Ski at nearby Ragged & Tenney Mountain resorts - Hike, bike & snowshoe at nearby 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.

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
4.98 out of 5 average rating, 207 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, 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!

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