Vacation rentals with a kayak in Wolfeboro

Find and book unique kayak rentals on Airbnb

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Popular amenities for Wolfeboro kayak rentals

House rentals with a kayak

Top guest favorite
The exterior of a lakefront cabin is surrounded by tall trees, showcasing a blend of greenery and hints of fall colors. A private dock extends into the calm water, with a canoe and kayak positioned along the shore, inviting outdoor activities.
Home in Wakefield
5 out of 5 average rating, 40 reviews

Modern Lakefront Cabin (Pet Friendly, King Beds)

DunjaRating, 5 stars1 week ago
Everything was beyond I expected . The hosts were great , place was clean , location was awesome . Quiet and peaceful. Will be back!
Top guest favorite
A custom-built home is situated among pine trees, featuring multiple large windows and a spacious porch that overlooks the natural surroundings. The driveway, lined with gravel, provides access to the inviting entrance. A campfire pit is visible in the yard, surrounded by greenery.
Home in Moultonborough
5 out of 5 average rating, 27 reviews

Lake Winnipesaukee Pine Family Paradise

JosephRating, 5 stars3 weeks ago
It was a wonderful stay. Steve is a fantastic host, and I would highly recommend to anyone looking to have a weekend stay with a big group! There’s great pickleball courts nearby, and it’s close to mount major! 10/10 experience!
Guest favorite
A modern lakefront home is nestled among trees, featuring large glass windows illuminating the interior. A fire pit surrounded by several wooden Adirondack chairs sits in the foreground, with a stone pathway leading to the house's entrance. Warm lights create a welcoming evening ambiance.
Home in Wakefield
4.86 out of 5 average rating, 22 reviews

Belleau Lake Escape

IsabellaRating, 5 stars2 weeks ago
A group of four of us visited this Airbnb this past weekend and we enjoyed our stay immensely, the house was cozy and had plenty of room for privacy whilst having nice common areas. The hosts were extremely friendly and helpful, they responded quickly to all of our questions and solved any inconveniences we encountered.
Superhost
A serene lakeshore scene captures the sun setting over Ossipee Lake. Gentle waves ripple towards the sandy shore, while mountains frame the background under a sky adorned with wispy clouds. The reflection of sunlight creates a shimmering path across the water.
Home in Freedom
4.86 out of 5 average rating, 95 reviews

Cozy camp for swimming, water sports and more!

BeckyRating, 5 stars3 weeks ago
The Pancake House was the perfect getaway! Peaceful, relaxing, comfortable, and charming! The house is better than the photos can show, and offered plenty of space for fun and relaxation. We enjoy evenings by the fire after enjoying the sunset on the lake!
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, 242 reviews

Waterfront w Kayaks, Pool table, Pergola, Firepit

DavidRating, 5 stars2 weeks ago
Great house with beautiful lake view and comfortable set up. Everything was clean and in good shape. Steve was responsive with communication and provided all the info we needed. I would recommend staying here.
Guest favorite
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
4.94 out of 5 average rating, 171 reviews

Blue Breeze - Private lakefront w/ Hot Tub

LynnRating, 5 stars1 week ago
We would definitely go back for another stay. Carl is a wonderful host and was very responsive and helpful. The house is beautiful and is located in such a tranquil and scenic location. We are a family of 6 along with our black lab and everyone fit comfortably. I highly recommend this place for a family get away.
Superhost
Two colorful kayaks, one red and one yellow, are positioned near a serene pond surrounded by lush greenery. A picnic table is located nearby, accompanied by a hammock suspended between trees, providing an inviting space to relax in nature.
Home in Harrison
4.9 out of 5 average rating, 307 reviews

Riverfront Luxury in the woods, Million $ Views.

AdamRating, 5 stars2 weeks ago
Property had amazing views. Inside was beautiful and very clean. Pond and river was nice. Host was quick with any question we had. would recommend.10/10
Superhost
An outdoor deck is presented, equipped with a round table and several chairs beneath a large umbrella. Surrounding trees provide shade, while distant views of Lake Winnipesaukee are visible, creating a serene outdoor dining space.
Home in Gilford
5 out of 5 average rating, 3 reviews

Coolest Condo on the Lake!

MicheleRating, 5 stars2 weeks ago
We enjoyed our short, but lovely stay at the lake! Home was beautiful and warmly decorated. Comfy beds and set up so nicely! View of lake was so nice and it was hard to leave the deck. We loved the peace and quiet, relaxing vibe! Loved the closed in porch too! Enjoyed pickleball so easily accessible and pretty walk to the lakefront to relax. Wish we could have stayed longer, but rain made it easier to leave. We had magical weather our full day! We hope to return to this special area and home. Loved the market so close though! Thank you!!

Cottage rentals with a kayak

Superhost
The two-story cottage is framed by lush greenery and features a spacious back deck with steps leading to the ground level. A fire pit is surrounded by several adirondack chairs, and a picnic table is positioned nearby on a grassy area.
Cottage in Conway
4.89 out of 5 average rating, 108 reviews

Cozy Pondside Retreat with direct water access!

TeraRating, 5 stars8 months ago
This place was really nice! Its on a beautiful lake with a lot to do! Jessica had plenty of kayaks, canoes, and life vests. The surrounding is beautiful and peaceful. The location is great with plenty of restaurants and shopping nearby. It's also very close to many great hiking areas Mt Washington.
Guest favorite
Cottage in Epsom
4.97 out of 5 average rating, 215 reviews

Smokey Pines Camp

CaryRating, 5 stars2 weeks ago
Smokey pines is the perfect getaway. It's private, secluded yet close to the towns and people we want to visit. It feels homey and comfortable and has all the amenities required. We'll definitely be back!
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
4.93 out of 5 average rating, 116 reviews

Cottage on the lake! Includes kayaks & rowboat!

ChristopherRating, 5 starstoday
This home at a lake was exactly as described, adorable, and the perfect relaxing getaway. You can't be more "on the water" without getting wet! Looking out over the lake in the morning with a cup of coffee, listening to the loons...awesome! Great location too as there are some great spots to eat nearby, simple drive to Portsmouth in one direction and Concord in the other. Our host was super informative and responsive, and the home was immaculate when we arrived. 10/10 would stay here again and would recommend!
Top guest favorite
A screen porch with a view of the lake features two red cushioned chairs and a matching bench, arranged around a small coffee table. A decorative patterned rug covers the floor, enhancing the cozy ambiance of this inviting outdoor space.
Cottage in Middleton
4.99 out of 5 average rating, 103 reviews

Lovely cottage on Sunrise Lake, Middleton, NH.

StephenRating, 5 stars2 weeks ago
They were accommodating, flexible, and very gracious. They had an entire binder of information with details about where to find fans, towels, flashlights, how to work the shower, heat, grill, and about anything else you can think of. It also had emergency services, restaurants, places to have a good time, and good details about checkout expectations. Overall we were extremely happy with the property and our stay, and were honored by the personalization they did for us specifically as it was our Honeymoon and they wrote us a custom note by hand for when we arrived. Highly Recommended - Will Rent Again!
Top guest favorite
A warm living area presents wooden walls and high ceilings, with abundant natural light filtering through large windows. Seating options include a cozy couch and a rocking chair. A wood stove is positioned near a flat-screen TV, complemented by a bookshelf and dining area in the background.
Cottage in Thornton
4.95 out of 5 average rating, 158 reviews

Cottage with antique charm view & river HSI Wi-Fi

JonRating, 5 stars1 day ago
The cottage was an excellent place to stay, a clean comfy environment with a wonderful yard.
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
4.94 out of 5 average rating, 110 reviews

Completely updated detached cottage/Paugus Bay!

ShaoyuRating, 5 stars7 months ago
We enjoyed a great weekend getaway at this place. Denise was a great host who were helpful and always quick to respond. The house is cozy and clean, perfect size for two adults. It is conveniently located while being private. We kayaked on Paugus Bay and hiked Mt Major. Would definitely come back again.
Superhost
The living area features a brown leather sofa paired with a decorative throw, surrounded by large windows that invite natural light. A textured area rug lies beneath a low coffee table, with decorative objects and plants adding a touch of greenery.
Cottage in Gilmanton
4.85 out of 5 average rating, 101 reviews

Hot Tub - Walk to the Beach - Mins to Mtns - Lakes

YannRating, 5 stars2 weeks ago
I had a nice stay at Alexa's. It's beautiful, quiet and ideal to get some rest while being surronded with nature. The best!
Superhost
A sunlit sunroom features a mix of comfortable seating, including a sectional sofa and two chairs, arranged around a wooden coffee table. Large windows allow natural light to fill the space, providing views of the surrounding greenery and seasonal foliage.
Cottage in Lyman
4.83 out of 5 average rating, 103 reviews

RK North : All season Waterfront cottage with dock

EricRating, 5 stars2 weeks ago
A Perfect Waterfront Escape – 5 Stars My wife and I had an unforgettable stay at RK North Waterfront Cottage. From the moment we arrived, we were welcomed by breathtaking views, fresh coastal air, and a sense of peaceful seclusion that made this trip truly special. The cottage itself was spotless, beautifully maintained, and tastefully decorated with cozy touches that made it feel like a true home away from home. We especially loved the spacious deck overlooking the water — perfect for morning coffee or evening wine while watching the sunset. The hosts were thoughtful and responsive, ensuring we had everything we needed without ever being intrusive. Whether it was relaxing by the fire pit, walking along the shore, or just enjoying the tranquility of the surroundings, every moment felt effortless and restorative. If you’re looking for a quiet getaway with charm, comfort, and stunning waterfront views, this is the place. We’re already planning our next visit. — Eric & Juliet DiNoto

Cabin rentals with a kayak

Guest favorite
The lakefront cabin is nestled among lush greenery, elevated on a wooden deck overlooking the water. Smooth stones lead down to the lake, with light filtering through the trees, creating a serene atmosphere in this natural setting.
Cabin in Andover
4.95 out of 5 average rating, 117 reviews

Little House on the Lake in the Forest

BrentRating, 5 stars1 week ago
Wonderfully peaceful, tranquil setting on the lake, in the woods. Perfect for a quiet getaway to reflect and renew. Everything was exactly as described, and Laurel was a gracious and responsive host. The cabin was rustic yet newly refinished, very clean, well equipped. Enjoyed the screened in gazebo, loved sitting by the water as well, plus experiencing the lake in the canoe and kayak. Also enjoyed some great hiking and views at Mt Kearsarge which is less than 20 minutes away. And finally -- the sounds of the loons after sunset. Grateful for three days of renewal!
Superhost
A private cabin is nestled among colorful autumn trees by Big Squam Lake. Various boats are moored along the shoreline, with hues of orange and gold from the foliage reflecting in the water. The peaceful scene is framed by gentle hills in the background.
Cabin in Holderness
4.87 out of 5 average rating, 105 reviews

Beautiful private cabin on Big Squam Lake

Pool HomesRating, 5 stars1 month ago
We had a wonderful stay and will definitely return! The cabin is lovely. My daughter enjoyed kayaking around the lake. We also enjoyed the science center, Walter’s basin, and birdwatching. Thank you!
Guest favorite
Cabin in Waterford
4.94 out of 5 average rating, 159 reviews

Lakeside Cabin Nestled in the Pines

LindseyRating, 5 stars7 months ago
Beautiful place. Lovely decorated. I would say that it is probably a little expensive for staying there in the winter/ fall time. Only one of us could sit on the couch at a time due to its location by the tv. The shower is really small and there is no room for toiletries in the bathroom at all. There is a rack but I had to keep all my bathroom stuff in bags the entire time because it is just lacking in space. I would think The price is worth it if you’re staying there in the summer and get to use the lake.
Guest favorite
A lakefront chalet is framed by lush trees, featuring a spacious deck with seating and a view of the water. A kayak rests on the sandy shore, leading to a clear lake that reflects the surrounding greenery and the home's inviting design.
Cabin in Barnstead
4.95 out of 5 average rating, 228 reviews

Scenic Lake and Ski Chalet: Hot Tub & Dreamy Views

MeaghanRating, 5 stars2 weeks ago
Stayed here for the second time with our family of five, including two toddlers and a baby. The house/property is the perfect setup for us! Everything is safe for kids and on one floor. There are things like pack-and-plays, kid dinnerware, kid toys/books, and sand toys provided. The sandy beach is close enough that our monitor reached from the baby’s room during nap time. Our oldest calls it “the little house” and has been talking about it since the last time we stayed here a year ago. It is the perfect little getaway! 🙂
Guest favorite
An aerial view captures the serene surroundings near Crystal Lake, showcasing a tree-lined road bordering the water. A private dock is visible, along with lush green foliage emphasizing the natural beauty of the area.
Cabin in Harrison
4.99 out of 5 average rating, 127 reviews

Get away at Crystal Lake

Natalia Wilkin Rating, 5 stars1 month ago
Wonderful Stay in a Great Location! Zak and Emily’s house was exactly as described. It has a fully equipped kitchen, a grill, and a fire pit outside, making it perfect for relaxing evenings. The house is stocked with towels and other essentials, so we had everything we needed. There’s also a ping pong table, which was a lot of fun, and a great collection of movies for entertainment. Check-in was super easy, and the house is conveniently located across from Crystal Lake, offering a peaceful and scenic setting. Communication with Zak and Emily was excellent—they responded quickly and were very accommodating. Overall, it was a fantastic experience, and I would highly recommend staying here for a peaceful getaway. Thanks again, Zak and Emily!
Guest favorite
The A-frame cabin is nestled among greenery, showcasing a wooden exterior with an angled roof. Steps lead to a raised deck that features outdoor seating. A gravel path leads to the cabin, surrounded by trees, offering a serene setting.
Cabin in Warren
4.92 out of 5 average rating, 114 reviews

Breezy Moose - A Frame Cabin/ Pet friendly

NicholasRating, 5 stars2 weeks ago
This beautiful A-Frame was a perfect weekend getaway. My girlfriend and I spent the weekend here and it was in a great location with perfect accommodations for two people. The place was clean with great amenities (grill, fireplace, etc.) Will definitely be hoping to return in the future / am eager to recommend this property to anyone.
Guest favorite
A brown wooden cabin is set among trees, showcasing large windows that provide natural light. The structure is elevated slightly above ground, with steps leading to a deck that extends outward. A gravel area surrounds the cabin, enhancing the natural landscape.
Cabin in Madison
4.92 out of 5 average rating, 134 reviews

Bear Cabin

AllysiaRating, 5 stars1 week ago
This was the perfect location for my husband and in laws. It was so peaceful. Thank you for a beautiful place to vacation.
Guest favorite
A fire pit area is surrounded by colorful Adirondack chairs in green, red, and blue. Lush trees provide shade, and a glimpse of the waterfront can be seen in the background, creating a serene outdoor atmosphere.
Cabin in Denmark
4.97 out of 5 average rating, 104 reviews

Lake Front with Private Dock - BRAND NEW Furniture

AaronRating, 5 stars2 months ago
This is an absolute beautiful place to stay. There is no question, I would 100% stay here again. My family had an amazing time here. Darryl was very easy to communicate with and made the stay very easy. If you’re looking for a clean and quiet place to stay, look no further.

Quick stats about vacation rentals with a kayak in Wolfeboro

  • Total rentals

    50 properties

  • Nightly prices starting at

    R1,616 ZAR before taxes and fees

  • Total number of reviews

    1.5K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

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