
Holiday rentals with a kayak in Ossipee
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Top-rated rentals with kayak in Ossipee
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.
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Popular amenities for kayak rentals in Ossipee
House rentals with a kayak

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!

In the Trees - NH w/ Lake Access
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.

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!

Cottage with antique charm view & river HSI Wi-Fi
Stephani was a great host! My friend group had a blast, the cabin was perfect and cozy especially after a day skiing at loon.

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!

Peaceful Lakeside Maine Retreat
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!

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

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.

Breezy Moose - A Frame Cabin/ Pet friendly
I can’t recommend this Airbnb enough! This place made us feel right at home. It was beautifully decorated, incredibly clean, equipped with everything we needed and even had some additional amenities (candles, clean blankets, grill accessories) that exceeded our expectations. The instructions for the home were clear, easy to follow, and the communication from Jerzy was proactive and kind. We truly settled in immediately. We were able to cook on the grill which was clean and easy to use, most neighbors had wood for sale that was purchased to build nightly fires, and the house itself was so comforting and peaceful. One of the best accommodations was being able to bring our pet who also felt right at home. We will 100% be back and can’t recommend it here enough! Thank you Jerzy!

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 holiday rentals with a kayak in Ossipee
Total rentals
20 properties
Nightly prices starting at
£30 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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- Wells Beach
- Loon Mountain Resort
- 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
- East End Beach
- King Pine Ski Area
- Cannon Mountain Ski Resort
- Tenney Mountain Resort
- Wentworth by the Sea Country Club
- Bear Brook State Park
- Omni Mount Washington Resort
- Mount Washington Cog Railway
- Bald Peak Colony Club