
Vacation rentals with a kayak in Ossipee
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Top-rated accommodations with a kayak in Ossipee
Guests agree: these accommodations with a kayak are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Ossipee kayak rentals
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!

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!

Waterfront Condo- Maine village retreat
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
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.

“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!

20ft from the Water with Mountain View!
Such a beautiful and cozy stay! literally feet from the water. It was incredible to wake up to that view. A cozy cabin feel with modern amenities. such a great space! thank you for having us

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.

Covered Bridge Cottage - Maine woods and river
From arriving to the hospitality throughout the stay to check out everything was just amazing!! Hidden gem for sure! Very relaxing cottage with a beautiful view. Very cozy, felt right at home. I used to live in Maine so returning for NYE and my daughter’s birthday and experiencing this after the fast pace living in Miami was an amazing experience, just what I needed!

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!

Private Beach, Lake Front, Family Friendly Cottage
Loved the place. Would definitely try to visit again!
Cabin rentals with a kayak

Private Hilltop Cabin, Lakes and Trails Abound..
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!!

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

Thompson Lake, No Cleaning Fee Pine Point Cottage,
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!!!

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.
Quick stats about vacation rentals with a kayak in Ossipee
Total rentals
20 properties
Nightly prices starting at
$55 CAD 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
- Pine Point Beach
- Peaks Island
- Squam Lake
- Moody Beach
- Cape Neddick Beach
- Goose Rocks Beach
- Scarborough Beach
- Hills Beach
- Loon Mountain Resort
- Fortunes Rocks Beach
- York Harbor Beach
- Wallis Sands Beach
- Drakes Island Beach
- Attitash Mountain Resort
- Goochs Beach
- Story Land
- Cranmore Mountain Resort
- Ogunquit Playhouse
- Long Beach
- Surfside Beach
- Pats Peak Ski Area