
Vacation rentals with a kayak in Ossipee
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Top-rated kayak rentals in Ossipee
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House rentals with a kayak

Luxury Lakehouse| Sunsets| Cen. Air| Private Dock
My girlfriends and I have chosen to stay here three years in a row for our annual girls weekend, which should tell you all you need to know. Clean, friendly and responsive hosts, great location for getting away to the quiet but easy drive to restaurants. Highly recommend!

Lakefront HotTub, Fireplace, Shop, Ski, Hike, Swim
we had a great time! the house was very clean and the location was perfect. just a short walk to the lake, which was very peaceful. the host was responsive and answered all of our questions.

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!

Lakefront Retreat with Dock and Fenced in Yard
This home was perfect for our family stay for a local wedding. It was a quiet relaxing place on the water! We enjoyed kayaking and sitting on the swing enjoying the view. The home included everything we needed and was very clean, spacious and comfortable. I would highly recommend this home to anyone looking in this area!

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.

Peaceful 4 bedroom lakehouse retreat
We had a fantastic time staying at Justin’s home!

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.
Cottage rentals with a kayak

“Stay Awhile in the Lake's Region”
We had a great time at Robert’s place. The home has everything you could want, and there are plenty of things to do in the area. It was a great home base for our weekend! The kids loved the game room!

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.

Cottage on the lake! Includes kayaks & rowboat!
we had the most peaceful and relaxing time. The cottage was adorable, clean and had everything you needed. The beds are so comfortable we have never slept so good away from home. the views of the lake are gorgeous 😍 we will be back for sure. The host was amazing as well giving recommendations of whats in the area and a sweet welcome basket.

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
We loved our stay! It ended up being a rainy weekend so we really enjoyed all the little extras the cabin had to offer - especially the crafting cabinet! The house has all these little helpful notes about how best to enjoy the house and your stay. The backyard is beautiful, the kitchen had great little additions (we always forget olive oil!). The beds were comfortable, our kids loved the bunk bed room. The location is great, close to local shops and small treasures but also near big chains should you need a specific item. The house really makes the most of the space. We will definitely be back!

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!

Thompson Lake, No Cleaning Fee Pine Point Cottage,
What an amazing hosts! When i check in they both came and visited and gave me a grand tour of things of the place. Showed where the lake was to kayak, recommended places to eat, and visited. Michael was quick to respond making sure i was doing great. I would totally go back and rent their place again! Thank you so much!

Rustic, cozy cabin on Sebago Lake. A hidden gem.
Came for the Fall colors; left in love with the place! Small but delightful. Cluttered in the most fantastical way. Nestled in paradise. Bonnie is so nice and friendly! Pay attention to the fact that the toilet is not attached to house. Short walk to privet and very clean!

Scenic Lake and Ski Chalet: Hot Tub & Dreamy Views
Me and my friends we were group of five. We enjoyed our stay at their place. It was amazing view by the lake side. The hot tub and kayaking experience was totally awesome. We will never forget our trip to Hampshire because of this beautiful house.

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.

Maine Lakes-Pleasant Mt-Private Trails
Lovely cabin in a beautiful location. Check in was easy and Jeff is a very responsive host. Highly recommend this spot.
Quick stats about vacation rentals with a kayak in Ossipee
Total rentals
20 properties
Nightly prices starting at
G$8,366 GYD before taxes and fees
Total number of reviews
1K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 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
- Attitash Mountain Resort
- Weirs Beach
- Owl's Nest Resort
- Long Beach
- Surfside Beach
- Long Sands 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
- Palace Playland
- Ferry Beach