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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

Superhost
An aerial view captures the lakeside cabin and surrounding greenery, with multiple buildings featuring blue roofs. A wooden dock extends into the water, and a few chairs are arranged near the shore. The serene lakeside environment is framed by trees and foliage.
Home in Northwood
4.94 out of 5 average rating, 17 reviews

Lakeside cabin w/ beach & dock

KatelynRating, 5 stars6 months ago
Amazing place to stay! Beautiful view right from the porch and plenty of room for everyone.
Guest favorite
Home in Wakefield
4.96 out of 5 average rating, 28 reviews

In the Trees - NH w/ Lake Access

AmyRating, 5 stars1 week ago
We had a wonderful stay at this cozy, comfortable, and peaceful home—perfect for our family of five! The space was quiet, private, and truly felt like a home away from home. It's in a beautiful location right by Lake Province, and we had almost everything we needed for our 3-night Easter weekend stay. Our older children attend UNH, and this was the perfect spot for us all to be together, relax, play games, and enjoy quality family time. We love to cook, and the brand new kitchen was gorgeous and a joy to use—we prepared three amazing meals together! Just a heads-up for fellow cooks: the kitchen is stocked with the basics, so if you're planning more elaborate meals, you might want to bring a few extra tools. The outdoor space was also a highlight! With beautiful weather all three days, we spent a lot of time outside enjoying the fire pit, string lights, grilling, eating al fresco, and just being together. We truly loved our stay and are already looking forward to coming back.
Guest favorite
A waterfront view presents a charming two-story house with a wrap-around porch, a gazebo sits nearby on a spacious lawn. Adirondack chairs are positioned towards the water, surrounded by trees and greenery, creating a serene outdoor space. The dock leads directly into the water.
Home in Sanbornton
4.95 out of 5 average rating, 37 reviews

Dog, Boat Friendly Waterfront home- no Airbnb fees

GwenRating, 5 stars8 months ago
This is an incredibly comfortable and remarkably well equipped lakefront house. Plenty of kitchen supplies and tools to keep the cooks happy, and all of the water gear anyone could ask for. We especially appreciated the large porch overlooking the lake. Close to the busy road (as was described in the listing), but blocked off and made visually private by fencing. Owners incredible, responding almost instantly, warmly, and generously.
Superhost
A view from the deck overlooks a tranquil river, framed by a large tree. A picnic table is positioned on the grassy area, with a pergola visible in the background. Snow patches contrast with the green grass, and colorful houses are reflected in the water.
Home in Laconia
4.92 out of 5 average rating, 239 reviews

Waterfront with Game Room Pergola Firepit Downtown

AmberRating, 5 stars2 months ago
The bed was so comfy! We had so much fun with the game room. It was such a cool addition
Superhost
Home in Barnstead
4.89 out of 5 average rating, 121 reviews

Lakefront home /3BR 2BA/ Dock/ Game room/ Garage

AdamRating, 5 stars2 months ago
Great house, quiet and peaceful. Ivars was very responsive. Enjoyed our stay!
Superhost
Lush greenery surrounds the serene lake, with tall trees lining the shore. A wooden dock is visible, providing access to the water, while the house is situated atop the hillside, partially obscured by foliage.
Home in Wakefield
4.88 out of 5 average rating, 16 reviews

Lakefront Retreat! Dog Friendly!

KimberlyRating, 5 stars8 months ago
This lake house was beautiful and the view is stunning! Every room is well appointed and perfect for setting a lake vacation vibe. The house has everything you could need. The description and pics on Airbnb are thorough and completely accurate. Jenna was an awesome host - very responsive and helpful and flexible. We will definitely be back!
Top guest favorite
A serene view of a grassy yard leading to a lake, bordered by trees. A sandy beach area is visible, with a wooden dock extending into the water. Two kayaks are situated on the grass, alongside a red paddleboat.
Home in Wakefield
5 out of 5 average rating, 8 reviews

The lake at your back door!

AdrianRating, 5 stars6 months ago
Irene was a great host! She reached out with very helpful information regarding the property and lake, which allowed us to prepare well for our stay. The house was clean, well-stocked, and exactly as pictured—perfect for a vacation getaway with friends!
Top guest favorite
Home in Danbury
4.98 out of 5 average rating, 55 reviews

Welcome to The Dam House!

SheriRating, 5 stars3 months ago
We had a great time staying at the Dam House. The house is a good size, clean and very cozy. It was just a few minutes from Ragged Mountain and was a perfect spot for our ski weekend!

Cottage rentals with a kayak

Superhost
A serene lakeside view showcases a small, wooden dock extending into the calm water. Two red kayaks rest on the grassy edge, surrounded by lush greenery and gentle hills in the background. Soft pastel hues of the sky hint at dusk.
Cottage in Conway
4.89 out of 5 average rating, 108 reviews

Cozy Pondside Retreat with direct water access!

TeraRating, 5 stars6 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.
Top guest favorite
A comfortable living area features a gray sofa and two armchairs, arranged around a round wooden coffee table. Light streams in through two windows, illuminating a neutral-colored area rug. Two lamps provide additional soft lighting, enhancing the inviting atmosphere.
Cottage in Alton
4.98 out of 5 average rating, 125 reviews

“Stay Awhile in the Lake's Region”

NetanyaRating, 5 stars1 month ago
I reached out to Bob about allowing one of my company crews to stay at his home, he allowed it which was awesome! The home was just as described, the crew were able to relax after working at a jobsite in the area and really enjoyed the home and the area. Bob was very responsive and easy to talk to. I will definitely be booking with Bob again when the crew needs to go back to the job site!
Top guest favorite
A cozy living area features warm wooden walls and a ceiling with exposed beams. Natural light fills the space through large windows adorned with red curtains. Comfortable seating includes a sofa and armchairs arranged around a rustic coffee table, with a small wood stove and a television nearby.
Cottage in Thornton
4.95 out of 5 average rating, 153 reviews

Cottage with antique charm view & river HSI Wi-Fi

AnnaRating, 5 stars2 months ago
Stephani was a great host! My friend group had a blast, the cabin was perfect and cozy especially after a day skiing at loon.
Guest favorite
A wooden waterfront deck is visible, featuring a circular table surrounded by six metal chairs. The setting sun casts a warm glow over the lake, creating a serene view of the water and distant shoreline.
Cottage in Laconia
4.94 out of 5 average rating, 110 reviews

Completely updated detached cottage/Paugus Bay!

ShaoyuRating, 5 stars6 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.
Guest favorite
A cozy cottage is depicted by the pond, surrounded by tall trees that reflect beautifully on the water's surface. The structure features large windows and a welcoming porch, providing a serene atmosphere amidst nature. Soft light enhances the tranquil setting.
Cottage in Conway
4.95 out of 5 average rating, 333 reviews

20ft from the Water with Mountain View!

ElizabethRating, 5 stars2 weeks ago
my partner and i stayed here to just get away from reality for a couple days! this lakeside cottage is the perfect place to do so. we couldn’t decide if we wanted to go out and about or stay right in the cabin, it was so peaceful! thank you for hosting!
Superhost
A serene lakeside view is presented, with tall trees framing a gently sloping landscape. The calm water reflects the surroundings, and a wooden dock extends into the lake, inviting outdoor activities in a tranquil setting.
Cottage in Waterboro
4.95 out of 5 average rating, 20 reviews

Quintessential Maine Lakefront Cottage.

BethRating, 5 stars8 months ago
Marina’s little cottage is a gem which we highly recommend. It is situated high above the peaceful and quaint lake providing interesting views. The sunrise while sitting on the dock was a favorite. A great place to get some reading done without everyday distractions. Everything was clean, neat and organized! The new kitchen was a treat! For a small place it is very spacious inside, beds and sitting areas comfy and everything one needs for a pleasant stay. Marina gets an A+ for communication. We may be back next year and will recommend it to friends and family. Please don’t hesitate to book this place for a relaxing getaway.
Top guest favorite
Cottage in Gilmanton
4.96 out of 5 average rating, 112 reviews

Private Beach, Lake Front, Family Friendly Cottage

RichardRating, 5 stars6 months ago
Loved the place. Would definitely try to visit again!
Superhost
A serene view of a lake surrounded by trees, reflecting the clear blue sky. The water's surface appears smooth, indicating calm conditions. The landscape features distant houses among the trees, contributing to a peaceful natural setting.
Cottage in Freedom
4.79 out of 5 average rating, 476 reviews

Lakefront, Beach Private, Amazing Views, & pets!

JemarisRating, 5 stars1 week ago
My boyfriend and I had an outstanding time at Helens cozy spot. We spent all day kayaking and canoeing in the beautiful lake. We absolutely loved this home and will miss it dearly. We'll hopefully be back another time. The dishwasher amenity was a life saver! We also hiked up Mount Willard via Crawford's notch (much to my surprise my boyfriend proposed up there!) This will be a get away I will never forget. Definitely stay at this lovely lake house.

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, 113 reviews

Little House on the Lake in the Forest

AnthonyRating, 5 stars2 months ago
Im not someone of many words, but it was an unbelievably cozy and wonderful experience
Guest favorite
Cabin in Bridgton
4.93 out of 5 average rating, 123 reviews

Private cabin w hot tub,skiing,firepit & mountains

DanRating, 5 stars2 weeks ago
This is a beautiful home that is very well maintained and cared for. Alexa's cabin was a great place for 5 of us to gather, relax, and enjoy. Kitchen has everything you need, the hot tub is fantastic during a spring snowstorm, the beds were very comfortable, and it provided ample space for us.
Guest favorite
The cozy A-frame cabin is set on a pebbled area surrounded by lush greenery. A wooden deck extends from the entrance, featuring a flag on display. The structure has large windows that allow for ample natural light, contributing to its inviting exterior.
Cabin in Warren
4.92 out of 5 average rating, 109 reviews

Breezy Moose - A Frame Cabin/ Pet friendly

LexiRating, 5 stars1 week ago
I can’t recommend this Airbnb enough! This place made us feel right at home. It was beautifully decorated, incredibly clean, equipped with everything we needed and even had some additional amenities (candles, clean blankets, grill accessories) that exceeded our expectations. The instructions for the home were clear, easy to follow, and the communication from Jerzy was proactive and kind. We truly settled in immediately. We were able to cook on the grill which was clean and easy to use, most neighbors had wood for sale that was purchased to build nightly fires, and the house itself was so comforting and peaceful. One of the best accommodations was being able to bring our pet who also felt right at home. We will 100% be back and can’t recommend it here enough! Thank you Jerzy!
Guest favorite
A wooden deck features a small round table surrounded by two black metal chairs. The serene view of a pond is visible in the background, framed by trees and a grassy area, creating a peaceful outdoor space.
Cabin in Madison
4.92 out of 5 average rating, 130 reviews

Bear Cabin

LilaRating, 5 stars1 month ago
Absolutely beautiful and peaceful stay. John and Cassie’s cabin was just as described and exactly what we were looking for. We drove up during a snow storm but the roads were plowed and well maintained. Very isolated and private but never felt unsafe or uncomfortable. Not too far from things to do but we were content enjoying the cozy relaxing home. John was quick to communicate with us if we needed anything and was very helpful.
Guest favorite
Cabin in Parsonsfield
4.96 out of 5 average rating, 222 reviews

Riverfront cabin between Portland & White Mtns.

ColinRating, 5 stars5 days ago
As advertised, but perhaps a bit smaller than it appears. Great location, and the host was responsive.
Guest favorite
The cabin is nestled among trees, with warm lighting glowing from its windows. A fire pit is visible in the foreground, surrounded by seating, while large rocks are strategically placed around the outdoor area.
Cabin in Denmark
4.95 out of 5 average rating, 184 reviews

Maine Lakes-Pleasant Mt-Private Trails

LoganRating, 5 stars3 weeks ago
We had a great time here! The cabin was incredibly comfortable and cozy. We especially enjoyed the hiking trails out back!
Guest favorite
The spacious main floor features a rustic log cabin design with a central dining table surrounded by black chairs. A well-equipped kitchen showcases wooden cabinets and a large stove, while a cozy seating area is visible in the background, accented by natural light from nearby windows.
Cabin in Wakefield
4.97 out of 5 average rating, 247 reviews

Beautiful Log Cabin on Belleau Lake -2900 sqft!

JohnRating, 5 stars1 day ago
Great properties around the lake Julie owns and operates was my second time staying at one of thier properties in the area. Great northern retreat for winter or summer !
Guest favorite
Cabin in Henniker
4.96 out of 5 average rating, 135 reviews

The SugarShack at Sweetwater

GregRating, 5 stars6 months ago
What an awesome spot! We will most definitely be back and stay longer next time. Can’t say enough how accommodating and welcoming Michele and Mike were. We enjoy riding the atv trails in the area and this location is perfect for that. You can ride to the trails from the cabin. The river is awesome, can’t wait to come back in the summer to enjoy it more ! Very clean and cozy.

Quick stats about vacation rentals with a kayak in Wolfeboro

  • Total rentals

    50 properties

  • Nightly prices starting at

    $90 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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