
Holiday rentals with a kayak in Midland
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Top-rated Accommodation with a Kayak in Midland
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Holiday House Rentals with a Kayak

2min walk to the beach & 20 min drive to Blue Mnt
We only stayed there for one night but it was a really good experience. The house is too comfortable, it is very nice and very spacious. It has everything you need at your fingertips. The kayak and bikes are souvenirs that are in very good condition and can be put to great use if you wish. Helen is very attentive, timely and willing. She responds extremely quickly to your questions and gives you solutions for everything in a friendly and warm manner.

Swan Cove Waterfront Retreat
We stayed here for a Family Day getaway recently. Very private and relaxing location with beautiful views of Georgian Bay. Evgenia was a wonderful host, very responsive and friendly and willing to go the extra mile to make our stay comfortable and memorable. I would definitely recommend staying here and look forward to returning.

Beautiful 6 BEDROOM Muskoka Cottage
Our stay here was fantastic. The house is big with plenty of rooms for a big group. It was clean and orderly. There is a beautiful dock with a canoe, kayak and life jackets. Our host Fred was very kind and accommodating. I would recommend this to anyone looking a cottage getaway.

Cozy Lakefront Cottage with Hot tub and Pool.
We went to this cottage for a beautiful romantic weekend getaway and we were happy we got that. The owner of the cottage Necker was very kind and helpful, absolutely loved the place and there was plenty of water activities to do. It was easy to check in, communicate and plenty of peaceful vibes. Recommended 100%, please go visit this cottage it is very well worth it. P.S: we loved the character of the cottage with little artpieces and wall art from all over the globe 🌎.

Beach House-S/W Exposure! Hot Tub, Sandy Water!
We stayed at Dylan’s place for the weekend with 13 adults and 4 kids. There was enough rooms and beds for all of us with adequate bedding and space. The house was clean and well equipped for our weekend! Before the stay we had lots of questions and Dylan was very responsive and answered everything in a timely manner and with lots of details. He was always following up during the weekend as well. The dock is beautiful and amazing! It was a bit buggy but that’s expected near the waters. We used the kayaks and boat and had a wonderful time!

The Muskoka River Homestead
Great place and great host..they were quick to respond to queries..and the big yard on the side was a big plus which other properties generally do not have..will be booking again next year..

Muskoka River Cabin
My friends and I had an amazing time at Ken and Rebecca’s place. We would love to visit again and highly recommend.

Sweet 4 bedrm Muskoka Lakefront Cottage
This cottage was the perfect winter getaway with friends!! It’s cottage-y feel & look with lots of pine is gorgeous and you can tell this cottage is very loved. Even though it’s not brand new or modern, its charm & true cottage feel/decor has been very well taken care of. The kitchen is FULLY stocked with everything you could need. The 4 bedrooms are cute, cozy and quite spacious. The 2 bathrooms are clean and very functional. The back deck, BBQ, outdoor fire pit and lake view were also so great. I’m sure this cottage would also be spectacular in the warmer months. Such a wonderful stay !!!!!
Cottages with a kayak

CozyPeaceful LakeCottage HotTub Canada
Our family enjoyed a nice, quiet stay at Sarah’s place. The view is beautiful, living space is spacious and comfortable, with good wifi, and fishing at the dock is a great way to enjoy some relaxed time. Sarah is very responsive for questions, which we thoroughly appreciate.

Charming cottage on Lake Muskoka
We had a wonderful time here on a short excursion out of the city! the cottage itself is magical with a beautiful view of the lake and a gorgeous back patio shaded by trees. Bryan and Pam were very helpful and had made sure to provide everything we needed and more

Lakefront Cottage with Sauna and Steam Room
We loved this place. From start to finish it was fantastic. Great location. Open and spacious. Everything we needed was provided. The host was very responsive and gave good clear instructions. We had a fantastic time to wind down.

Lake Muskoka Classic Cottage w/ Hot Tub
We had a group weekend getaway and loved our stay! The house is very spacious and beautifully decorated. The host Ashley was very responsive and friendly. Highly recommend to anyone who wants a beautiful escape to recharge!

Baysong Cottage, Hot Tub and Sauna on Georgian Bay
Great time, Great Fun, Great place to enjoy! We really enjoyed our stay with family here! All The Best!

CARL in Muskoka: Waterfront Cottage with Hot Tub
My friends and I stayed here for a winter weekend away and it was just what we needed/wanted in a little cottage. Great location for those coming from the GTA and nice and close for those in Simcoe. Once we got there we felt right at home! The hosts had cleared the walking paths and back deck of any recent snow fall which made it nice and easy to get inside and enjoy the grounds. They went above and beyond by having the wood burning stove going for us when we checked in which made CARL that much more cozy and welcoming. Communication and instructions were very clear and detailed from start to finish which made the whole rental process easy and enjoyable. My friends and I look forward to coming back to CARL in the future!

Tree Tops on Six Mile Lake
Really clean and cozy cottage,private and quite too.

Gorgeous Muskoka Getaway on stunning private lake
Amy is an outstanding host who goes above and beyond to ensure your stay is phenomenal. The cottage was a perfect getaway and had everything needed - including a beautiful view!
Cabin rentals with a kayak

Oak Cabin on Sparrow Lake
The place had everything we needed—clean, peaceful, and filled with activities, especially fishing, which we really enjoyed. We were also so happy to spot river otters during our stay! Big thanks to Ash and Nicholas for being so accommodating with our inquiries. We just got home and are already wishing we could go back!

Reay Lake Tiny House
We stayed at Laura's cabin on our honeymoon and it was amazing! We love the outdoors and if the weather has cooperated we would have taken the kayaks out onto the lake. If your looking for a quick quiet getaway close to Gravenhurst with all the amenities of cottage county, this is your place to stay! The cabin was clean, stocked with all your kitchen essentials you will need.

The Blue Cottage
Jennifer was great. We all loved the space. Very cozy and beautiful view. Also enjoyed the kayaks and hanging at the dock. Wasaga Beach is nearby and we enjoyed spending time at the beach. There is an awesome cafe on site by the cottages which was fantastic. Overall a Greta experience. Highly recommend and would love to come back.

Lake view Blue cabin by the bay
The place was relaxing and we felt like we’re home.

Beautiful Six Mile Lake Muskoka
Great place, super well kept and beautiful. It has all you need for an awesome cottage experience and the perfect getaway

Waterfront A-frame in Muskoka
We stayed for 4 nights at this cottage in late September, just as the autumn leaves were setting in. It was rainy at night but we enjoyed cozy nights watching The Hobbit or playing board games by the roaring fireplace. During the days, we did multiple hikes around Hardy Lake, went to Bala (a very quaint town-we made jokes about being in a cheesy Hallmark movie), toured the cranberry bogs and trails with hot wine drinks and just enjoyed time at the cottage. There is something for everyone whether you’re a cook, book-lover or outdoors enthusiast. We brought our two dogs who loved hiking the trails, watching chipmunks, swimming near the shore , and lounging on the dock. They even got into the canoe. There was a friendly senior dog who wandered down to say hi a couple times. The highlight of it all- we got engaged there! :) :) :) Sarah and Chris, you must be so proud of this enchanting cottage where so many special life moments were created.

SIMS Cozy Muskoka River Cabin
We had an amazing stay at this Airbnb in Muskoka! The place was spotless, well-equipped, and perfect for our group getaway. The hosts were incredibly friendly and responsive — they replied to any questions within minutes, which made everything so smooth and stress-free. They went above and beyond by providing everything we could possibly need: fresh towels, shampoo, body wash, detergent, even bug spray and life jackets for kayaking. It was clear they really care about their guests' comfort and experience. We absolutely loved the place and enjoyed every moment of our staycation. Highly recommend to anyone looking for a relaxing and well-hosted getaway in Muskoka!

Charming Muskoka cottage, amazing views!
We had a wonderful stay at Annmarie’s cottage. The house was fully stocked with anything you might possibly need for a weekend away. Communication was excellent - Annmarie’s clear and proactive instructions made it a breeze to find and access the cottage. Whether in the cottage, on the deck or on the dock, the view of the bay is spectacular. We would definitely stay again!
Quick stats about holiday rentals with a kayak in Midland
Total rentals
30 properties
Nightly prices starting at
$101Â NZD before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
- Grand River Holiday rentals
- Brampton Holiday rentals
- Muskoka Lakes Holiday rentals
- Vaughan Holiday rentals
- Georgian Bay Holiday rentals
- Markham Holiday rentals
- Tobermory Holiday rentals
- Kitchener Holiday rentals
- Waterloo Holiday rentals
- Mississauga Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Rentals with outdoor seating Midland
- Rentals with a fireplace Midland
- Rentals with beach access Midland
- Rentals with pools Midland
- Rentals with lake access Midland
- Rentals with a washing machine and dryer Midland
- Pet-friendly rentals Midland
- Beachfront rentals Midland
- Kid-friendly rentals Midland
- Fitness-friendly rentals Midland
- House rentals Midland
- Apartment rentals Midland
- Rentals with an EV charger Midland
- Cottage rentals Midland
- Cabin rentals Midland
- Waterfront rentals Midland
- Rentals with a hot tub Midland
- Rentals with a patio Midland
- Rentals with a fire pit Midland
- Family-friendly rentals Midland
- Rentals with a kayak Simcoe County
- Rentals with a kayak Ontario
- Rentals with a kayak Canada
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
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- Holiday Chalets United Kingdom
- Cottage Rentals United States
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- Holiday Apartments Australia
- Holiday Houses United States
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- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Blue Mountain Village
- Port Carling Golf & Country Club
- Osler Bluff Ski Club
- Horseshoe Resort
- Devil's Glen Country Club
- Georgian Bay Islands National Park
- Beaver Valley Ski Club
- Mount St. Louis Moonstone
- Snow Valley Ski Resort
- Lake Joseph Golf Club
- Muskoka Lakes Golf and Country Club
- The Georgian Peaks Club
- The Club At Bond Head
- Muskoka Bay Resort
- Rocky Crest Golf Club
- Alpine Ski Club
- National Pines Golf Club
- Barrie Country Club
- Windermere Golf & Country Club
- The Georgian Bay Club
- Craigleith Ski Club
- Muskoka Highlands Golf Links
- South Muskoka Curling and Golf Club
- Mansfield Ski Club