
Vacation rentals with a kayak in Wolfeboro
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Top-rated kayak rentals in Wolfeboro
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Popular amenities for Wolfeboro kayak rentals
House rentals with a kayak

Modern Lakefront Cabin (Pet Friendly, King Beds)
Everything was beyond I expected . The hosts were great , place was clean , location was awesome . Quiet and peaceful. Will be back!

Lake Winnipesaukee Pine Family Paradise
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!

Belleau Lake Escape
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.

Cozy camp for swimming, water sports and more!
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!

Waterfront w Kayaks, Pool table, Pergola, Firepit
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.

Blue Breeze - Private lakefront w/ Hot Tub
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.

Riverfront Luxury in the woods, Million $ Views.
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

Coolest Condo on the Lake!
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

Cozy Pondside Retreat with direct water access!
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.

Smokey Pines Camp
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!

Cottage on the lake! Includes kayaks & rowboat!
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!

Lovely cottage on Sunrise Lake, Middleton, NH.
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!

Cottage with antique charm view & river HSI Wi-Fi
The cottage was an excellent place to stay, a clean comfy environment with a wonderful yard.

Completely updated detached cottage/Paugus Bay!
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.

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

RK North : All season Waterfront cottage with dock
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

Little House on the Lake in the Forest
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!

Beautiful private cabin on Big Squam Lake
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!

Lakeside Cabin Nestled in the Pines
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.

Scenic Lake and Ski Chalet: Hot Tub & Dreamy Views
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! 🙂

Get away at Crystal Lake
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!

Breezy Moose - A Frame Cabin/ Pet friendly
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.

Bear Cabin
This was the perfect location for my husband and in laws. It was so peaceful. Thank you for a beautiful place to vacation.

Lake Front with Private Dock - BRAND NEW Furniture
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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- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Squam Lake
- Scarborough Beach
- York Harbor Beach
- Story Land
- Loon Mountain Resort
- North Hampton Beach
- Attitash Mountain Resort
- Weirs Beach
- Owl's Nest Resort
- Long Beach
- Surfside Beach
- Long Sands Beach
- Rye North Beach
- Franconia Notch State Park
- Pats Peak Ski Area
- Bear Brook State Park
- Wentworth by the Sea Country Club
- Mount Washington Cog Railway
- East End Beach
- Cranmore Mountain Resort
- Cannon Mountain Ski Resort