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Vacation rentals with a kayak in Grey Highlands

Find and book unique kayak rentals on Airbnb

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Popular amenities for Grey Highlands kayak rentals

House rentals with a kayak

Guest favourite
Home in Wasaga Beach
4.88 out of 5 average rating, 110 reviews

20 min from Blue Mountain -Relax & Enjoy Winter

TawnyaRating, 5 stars2 months ago
Such a great place to stay after skiing at Blue Mountain! Definitely recommend.
Top guest favourite
Home in Meaford
4.96 out of 5 average rating, 99 reviews

Modern Country Getaway by the Bay

PriyaRating, 5 stars6 days ago
I had a fantastic stay at Ginny’s property! It was extremely clean, easy to find, and beautifully located right by the lake. The lake was absolutely stunning and added such a peaceful, relaxing touch to the experience. The property itself is beautiful and well cared for, and the host was very accommodating and responsive throughout our stay. I’ll definitely be coming back, and I highly recommend this place to anyone looking for a serene getaway!
Guest favourite
Home in Durham
4.9 out of 5 average rating, 165 reviews

Heron's Perch

SergioRating, 5 stars8 months ago
This was our second year at Carrie and Dan's cottage and once again my family and I had a fantastic time. The house is perfectly situated on the river with a nice beach and it has all of the amenities needed. Dan communicated regularly and checked in with us to ensure we had everything we needed. This is a beautiful property which anyone would have fun at.
Superhost
Home in Coldwater
4.68 out of 5 average rating, 82 reviews

Muskoka Cottage on the Severn River

SumeyRating, 5 stars8 months ago
great place great location on the water. hope to be back in a couple of years. boat launch is 5mins away, great for fishing off the dock
Guest favourite
Home in Meaford
4.92 out of 5 average rating, 110 reviews

Charming 3 bed house, your gateway to Georgian Bay

RuthRating, 5 stars2 weeks ago
Lovely spot to stay with the family. We had such a nice weekend. Meaford is great place and close to both Owen sound and Collingwood to explore further. The house was comfortable and a great place for our family and dog to relax. It had everything we needed
Guest favourite
Home in Gravenhurst
4.83 out of 5 average rating, 322 reviews

Beautiful 6 BEDROOM Muskoka Cottage

MaryRating, 5 stars3 months ago
Fred’s house was great! The house’s open concept was large enough for all of us (6 adults) to hang out in through the cold winter days without feeling crowded. The fireplace added lovely ambience and warmth. The six bedrooms ensured we all had our own space, which was a nice treat for our girls’ weekend. The master bedroom with ensuite was particularly spacious. The whole house was nicely decorated, and overall was a cozy and welcoming place. We didn’t use the sunroom, as is unfortunately smelled of smoke. Fred was a very responsive host. He quickly answered any questions. We had a lovely stay here, and wouldn’t hesitate to fully recommend it.
Top guest favourite
Home in Wiarton
4.96 out of 5 average rating, 146 reviews

Kiss & Bond Water View Colpoys Bay 4 -Seasons

VaibhavRating, 5 stars1 week ago
Great place. we really enjoyed the stay... hoping for the visit soon... thank you Geraldine...
Guest favourite
Home in Georgina
4.91 out of 5 average rating, 270 reviews

Beach House-S/W Exposure! Hot Tub, Sandy Water!

SamanthaRating, 5 stars4 weeks ago
Dylan’s place was better than anticipated. Large, well-laid out, clean, beautiful views and well-stocked. I think most impressive was Dylan himself who was extremely responsive and friendly. He is a SuperHost. I would absolutely come back,

Cottage rentals with a kayak

Top guest favourite
Cottage in Severn Bridge
5 out of 5 average rating, 136 reviews

CozyPeaceful LakeCottage HotTub Canada

UsamaRating, 5 stars5 days ago
This space is everything you need to wind down and relax! The location is amazing, the house is lovely and exactly as described, and the hosts are super responsive if you have any issues, which we didn’t. We loved using the different water sport equipment to have fun on the lake and the hot tub was amazing! We will definitely be coming back
Top guest favourite
Cottage in Wiarton
4.98 out of 5 average rating, 110 reviews

Waterfront Cottage by Bruce Trail

SamanthaRating, 5 stars1 month ago
We just returned from a weekend stay at this beautiful cottage and it was exactly what we were looking for. Peaceful and picturesque, right on the water with all the amenities we needed. Ildiko was quick to respond if we had any questions and was accommodating where we had some requests regarding check out. An absolute gem of a place, amazing views and spectacular sunrises. Would definitely recommend staying here. We would love to be back in the warmer months to experience the additional facilities such as kayaking. Thank you for your hospitality, Ildiko, we look forward to our next visit!
Superhost
Cottage in Washago
4.88 out of 5 average rating, 126 reviews

Vintage Farmhouse Lakeview and Golfers Cottage

MajidRating, 5 stars2 months ago
We had a great stay at the cottage. The place was exactly as shown in the photos and description. Sandra was very responsive which was very helpful. Lots of ski and snowshoeing opportunities around in the winter, definitely worth the experience!
Top guest favourite
Cottage in Innisfil
4.98 out of 5 average rating, 129 reviews

Charming waterfront cottage on Lake Simcoe

NiloufarRating, 5 stars6 months ago
We enjoyed our stay. More beautiful than the pictures. Caroline was very responsive. She offered us early check-in and accepted to check out at 11am instead of 10am. can't wait to go back in summer.
Guest favourite
Cottage in Wiarton
4.94 out of 5 average rating, 34 reviews

Stunning lakefront cottage

AhmedRating, 5 stars6 months ago
Absolutely enjoyed our stay at Brent's cottage! Well equipped spot with as much seclusion as you need for a fun time
Superhost
Cottage in Orillia
4.87 out of 5 average rating, 108 reviews

FRIEND LAKE HOUSE

PruthviRating, 5 stars2 weeks ago
I had an amazing experience at this Airbnb! Denial and Alex were incredibly responsive and went above and beyond to ensure everything was perfect during my stay. The communication was seamless, and they were always available to answer any questions promptly. The place itself was spotless, beautifully designed, and located in a fantastic neighborhood. It was even better than the pictures! Everything I needed was provided, and the thoughtful little touches made it feel like a home away from home. I wouldn’t hesitate to stay here again and recommend it to anyone looking for a comfortable and enjoyable stay. Thank you, Denial and Alex, for such a wonderful experience!
Superhost
Cottage in Waubaushene
4.84 out of 5 average rating, 153 reviews

Georgian Bay with Hot Tub & Sauna, on Tay Trail !

EmilyRating, 5 stars4 days ago
Stephen's place felt like home while our home was under renovation. we enjoyed the walk on the trail to watch the sunsets! A fantastic, accomodating,host.
Superhost
Cottage in Port Severn
4.92 out of 5 average rating, 102 reviews

Tree Tops on Six Mile Lake

DanyelleRating, 5 stars6 months ago
From beginning to end we had a great experience. The home had gorgeous views and fall colours, the home was comfortable, the bedrooms cozy and the beds, comfortable. The kitchen living dining open area made for a great communal atmosphere and we had great fireside chats. The weather was gorgeous so it allowed us to do yoga on the expansive deck. It was an all round wonderful stay and Agatha was very responsive to questions.

Cabin rentals with a kayak

Guest favourite
Cabin in Severn Bridge
4.91 out of 5 average rating, 32 reviews

Oak Cabin on Sparrow Lake

SteveRating, 5 stars2 months ago
Good value. We were looking for something humble and didn't want to break the bank. This is a very nice spot with that special something. We were snowed in our entire stay but the space was well set up for that, with TV's in each room with internet and apps. Really kind host. I would recommend this place and we would book again.
Guest favourite
Cabin in Mar
4.96 out of 5 average rating, 191 reviews

Heaframe - An A-Frame cabin in the woods

TanyaRating, 5 stars4 months ago
We had a wonderful stay at Heaframe. Our girls loved the toys and games, and we enjoyed the sauna every day. Perfect place to enjoy a few relaxing days over the holiday break. Hosts are very responsive and friendly. We’ll be back!
Guest favourite
Cabin in Waubaushene
4.88 out of 5 average rating, 8 reviews

Lake view Blue cabin by the bay

LaniRating, 5 stars8 months ago
The place was relaxing and we felt like we’re home.
Guest favourite
Cabin in Lion's Head
4.92 out of 5 average rating, 224 reviews

Little Lake Lookout: Sauna, Beach, Dock, Dogs!

NathalieRating, 5 stars1 week ago
5+++++....We loved our stay at Little Lake Lookout ! It was so nice to find a place that welcomed our dog. The setting for the dogs is WOW!!!  When they say pet-friendly, it is the best one for sure. It is so nice to be able to let your dogs out late at night and not have to put them on a leash to go potty. That fenced yard with all the sensor lights and little patio lock doors is such a plus. This cottage is TOP NOTCH and made our stay incredibly tranquil, perfect for a relaxing getaway. I just can't say enough about this place, so many thoughtful touches! Waking up to this amazing lake view was so beautiful. The cottage was so clean when we got there, you can't tell it was a pet-friendly place. We were very impressed. We had everything we needed for the best vacation. The host, Elizabeth, was so nice and always quick to respond to our questions. Highly recommend for anyone looking to unwind with their furry babies!!! Looking forward to our next vacay there.
Top guest favourite
Cabin in Southgate
4.97 out of 5 average rating, 35 reviews

Two - YES 2 cozy cabins !

MirandaRating, 5 stars4 days ago
This cabin rental is beautiful. The river is so peaceful sounding and you have everything you need to relax and enjoy a quick little get away. We stayed as guests for a wedding near by and it accommodated me as a single well in the smaller cabin and my friend and her baby in the larger cabin. This was an excellent find! Scott was communicative and professional and everything was easy.
Guest favourite
Cabin in Meaford
4.89 out of 5 average rating, 28 reviews

Skipping Rock Cabin: Cozy Charm & Hot Tub Bliss

AlexRating, 5 stars4 weeks ago
This cottage was great! We appreciated the super well-equipped kitchen, as well as all of the items available for kids. It was a relaxing week with great views of the lake from the cottage, hot tub, and fire pit. Very thankful they were able to accommodate us on short notice and will happily try and come back again!
Superhost
Cabin in Port Severn
4.86 out of 5 average rating, 14 reviews

Beautiful Six Mile Lake Muskoka

DanRating, 5 stars6 months ago
amazing spot very cozy, absolutely stunning. Madeline was very helpful and accommodating. the only issue was we couldn't find a broom to sweep the floors when we left lol. so I give a full star rating thanks for letting us check in early and allowing us to park the trailer at the Airbnb while we went atving in the beautiful area. this is a must book for anyone and everyone
Superhost
Cabin in Severn
4.8 out of 5 average rating, 15 reviews

Cabin 2, a cozy two bedroom Muskoka cabin

KarensaRating, 5 stars23 months ago
Definitely will be booking again. Very relaxing!

Quick stats about vacation rentals with a kayak in Grey Highlands

  • Total rentals

    50 properties

  • Nightly prices starting at

    $84 CAD before taxes and fees

  • Total number of reviews

    1.6K reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Grey County
  5. Grey Highlands
  6. Rentals with a kayak