
Holiday rentals with a kayak in Ossipee
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Top-rated Accommodation with a Kayak in Ossipee
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.
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Holiday House Rentals with a Kayak

Funky Lake House
We had a great time at Laurie’s place. Highly recommended and hopefully we will be back soon. Thanks !

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

Open concept 4 bedroom Lakehouse
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!

Lakeside cabin w/ beach & dock
Amazing place to stay! Beautiful view right from the porch and plenty of room for everyone.

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

Waterfront with Game Room Pergola Firepit Downtown
The bed was so comfy! We had so much fun with the game room. It was such a cool addition

Lakefront home /3BR 2BA/ Dock/ Game room/ Garage
Great house, quiet and peaceful. Ivars was very responsive. Enjoyed our stay!

Secluded Lakehouse/2 private docks*Hottub*big yard
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!
Cottages 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.

“Stay Awhile in the Lake's Region”
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!

Smokey Pines Camp
Words can’t describe the view from the patio. It was a wonderful, peaceful escape from everything!

Cozy camp near highland lake
My stay here was absolutely awesome—cozy, charming, and full of thoughtful touches that made it feel like a home away from home. Tucked away in a quiet spot, it had just the right mix of comfort and style, with a super comfy bed, a well-equipped little kitchen, and warm lighting that made evenings feel magical. The host went above and beyond, leaving local tips and a welcome treat that totally made my day. I honestly didn’t want to leave! And the view to the lake was so beautiful especially the sunsets for the cabin overlooking everything was just so awesome!

20ft from the Water with Mountain View!
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!

RK North : All season Waterfront cottage with dock
It was overall a tremendous experience. I would definitely recommend it!

Private Pond Escape: Luxe Cottage/Private Isle
This place is the perfect reminder of the kind of place you wish to retire at. I can’t wait to come in the summer or fall! Interestingly enough we came during April snow weather and still had the best and most relaxing time. It was a huge plus that Cumberland farms was two minutes away and a lot of other local stores were around. Extremely dog friendly and truth be told any dog’s favorite place this would easily be. I brought my puppy and it was a great way to expose him to ALOT. Mary was so responsive and helpful and we actually got stuck in the mud and her whole family plowed us out and we got a laugh at the end as well in the midst of it all. The place was clean, you really felt at home with all amenities that were included, I would just keep in mind there was not a kitchen aide mixer so bring a handheld mixer and that would do the trick depending on what you’re planning on baking but I was able to make a lot of things without. Highly recommend, very peaceful, and all you need.

Peaceful Cottage on Maine Flower Farm
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!
Cabin rentals with a kayak

Sunday River & Lake Chalet, 2 Kitchens, Hot Tub
My friends and I had a great time relaxing at this beautiful place. Aqeel and Michelle were extremely responsive and helpful when necessary. We would stay again!

Little House on the Lake in the Forest
Im not someone of many words, but it was an unbelievably cozy and wonderful experience

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!

Get away at Crystal Lake
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.

Private cabin w hot tub,skiing,firepit & mountains
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.

Bear Cabin
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.

Riverfront cabin between Portland & White Mtns.
As advertised, but perhaps a bit smaller than it appears. Great location, and the host was responsive.

The SugarShack at Sweetwater
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 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
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- Ogunquit Beach
- Wells Beach
- Sebago Lake
- Squam Lake
- Scarborough Beach
- Loon Mountain Resort
- York Harbor Beach
- Attitash Mountain Resort
- Story Land
- Cranmore Mountain Resort
- Ogunquit Playhouse
- Long Beach
- Surfside Beach
- Pats Peak Ski Area
- Owl's Nest Resort
- Wildcat Mountain
- Ragged Mountain Resort
- Long Sands Beach
- Purity Spring Resort
- Franconia Notch State Park
- Cannon Mountain Ski Resort
- East End Beach
- King Pine Ski Area
- Tenney Mountain Resort