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Holiday rentals with a kayak in Ossipee

Find and book unique kayak rentals on Airbnb

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Popular amenities for Ossipee kayak rentals

Holiday House Rentals with a Kayak

Superhost
Home in Tamworth
4.82 out of 5 average rating, 96 reviews

Lakefront HotTub, Fireplace, Shop, Ski, Hike, Swim

ShaunaRating, 5 stars2 months ago
The place is clearly well taken care of with attention to detail. This would be a great place any time of year. Miriam and the home were very accommodating. I would return to this location with great peace of mind.
Top Guest favourite
Home in Norway
4.99 out of 5 average rating, 83 reviews

Open concept 4 bedroom Lakehouse

ErikRating, 5 stars1 month ago
Great winter weekend stay in Maine, the house was very cozy and perfect for our group. The location is perfect for access to the ski mountains and the town as well. Overall highly recommend Roman’s place, I’m sure it is just as beautiful in the summer!
Guest favourite
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 favourite
Home in Newfield
4.97 out of 5 average rating, 30 reviews

Peaceful 4 bedroom lakehouse retreat

JessicaRating, 5 stars3 months ago
We had a fantastic time staying at Justin’s home!
Superhost
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!
Guest favourite
Home in Shapleigh
4.96 out of 5 average rating, 146 reviews

Secluded Lakehouse/2 private docks*Hottub*big yard

CarlyRating, 5 stars1 month ago
We had a wonderful stay at this home for a mother daughter weekend end of March. Great location for each of us coming from different states in New England. The home was very clean, each of us commented on how comfortable the beds were, also loved the good quality linens. The huge dining table was unique for a rental and was awesome for sharing meals and doing arts & crafts. Lots of space and seating in the living room as well. Highly recommend staying here!
Guest favourite
Home in Sanford
4.88 out of 5 average rating, 40 reviews

Waterfront Condo- Maine village retreat

DiannaRating, 5 stars5 months ago
We had a great stay! Loved the views and hot tub. It was so close to town but felt private with the privacy fence. Owners were very responsive! Thanks for a great stay

Cottages with a kayak

Superhost
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 favourite
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!
Guest favourite
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
Cottage in Lyman
4.82 out of 5 average rating, 101 reviews

RK North : All season Waterfront cottage with dock

BrianRating, 5 stars2 weeks ago
It was overall a tremendous experience. I would definitely recommend it!
Guest favourite
Cottage in Standish
4.92 out of 5 average rating, 118 reviews

Peaceful Lakeside Maine Retreat

SarahRating, 5 stars5 months ago
The home was in a beautiful location and it was so peaceful to wake up and look out over the water. The beds were comfortable and there was lots of space for our group to hang out. The host was very accommodating and answered all our questions quickly. Highly recommend!
Guest favourite
Cottage in Buxton
4.98 out of 5 average rating, 142 reviews

Peaceful Cottage on Maine Flower Farm

RaeganRating, 5 stars6 months ago
Perfect fall cottage so close to Portland! The cottage is so peaceful and quiet. But so close to Portland but you wouldn’t even know it. The farm is lovely and we took a walk down to the river on the property, it was so peaceful and so much land! If you are looking for a get away from a city, but want to be able to explore Portland and Kennybunks, this was the perfect spot. I don’t know if I’ve slept that good all year. Would definitely come back again. And we love Trooper the dog!
Top Guest favourite
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
Cottage in Parsonsfield
4.88 out of 5 average rating, 156 reviews

Riverpine Retreat - clean&bright waterfront home

ShariRating, 5 stars2 weeks ago
We spent nearly a week at the cabin. We had sun, snow and rain while we were there, but we didn’t care! The cabin is comfy and cozy. It had everything we wanted for a relaxing visit, including a fireplace. The decor is cute and comfy. The bathroom, including the shower and BIG towels, was perfect. Nestled in the trees, on the river, it uwill be an awesome place to visit this summer.

Cabin rentals with a kayak

Top Guest favourite
Cabin in Windham
4.92 out of 5 average rating, 205 reviews

Private Hilltop Cabin, Lakes and Trails Abound..

PeterRating, 5 stars7 months ago
We had the absolute best time at MJ’s place, highly recommend !! The house is spatious yet very cozy and quiet, with a nice back porch to sit and enjoy the surrounding woods! Home is also very close to town and to Poryland/coastline, and the cleanest lake to swim in that we’ve ever been to! MJ was very helpful and quick to respond. Stay here! We hope to return sometime soon!!
Guest favourite
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
Top Guest favourite
Cabin in Oxford
4.94 out of 5 average rating, 132 reviews

Thompson Lake, No Cleaning Fee Pine Point Cottage,

BeatriceRating, 5 stars3 days ago
Mike & Kathy are the perfect hosts (hands down), they are easy to get in touch with, fair & very welcoming. Would hundred percent recommend them and their place. Awesome lake front property!!!
Superhost
Cabin in Raymond
4.93 out of 5 average rating, 154 reviews

Rustic, cozy cabin on Sebago Lake. A hidden gem.

WaltRating, 5 stars6 months ago
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!
Guest favourite
Cabin in Harrison
4.99 out of 5 average rating, 125 reviews

Get away at Crystal Lake

GabrielRating, 5 stars3 months ago
Great cabin, location, and hosts. Our group had a great time coming back for our second trip here and would highly recommend. 5 stars all around.
Guest favourite
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 favourite
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 favourite
Cabin in Parsonsfield
4.96 out of 5 average rating, 222 reviews

Riverfront cabin between Portland & White Mtns.

ColinRating, 5 stars3 days ago
As advertised, but perhaps a bit smaller than it appears. Great location, and the host was responsive.

Quick stats about holiday rentals with a kayak in Ossipee

  • Total rentals

    20 properties

  • Nightly prices starting at

    $62 AUD 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

Destinations to explore