
Cottage vacation rentals in Midland
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Top-rated cottage rentals in Midland
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Midland cottage rentals
Cottage rentals with a hot tub

Waterfront cottage on quiet Spence lake
This is a beautiful place to stay, right on the lake with an amazing view, and a friendly beaver right next door! Our highlights were the hot tub, the fire pit and kayaking on the lake. This spot would be amazing in the Summer. The house is clean and well set up, the 2 downstairs bedrooms are small but just fine for sleeping. There is plenty of room in the rest of the house.

Beautiful Four Bedroom Lagoon City Waterfront Home
Daniel gave a thorough intro message of specifics the day of on top of what was already so clearly laid out. The property was beautiful with access to so many activity options. House is clean and spacious. We spent a lot of time on the dock which had a great selection of furniture and sun/shade options. The beach is a close walk. We thoroughly enjoyed our weekend and will likely be back to enjoy the space again!

Muskoka Waterfront Cottage - HOT TUB & SAUNA
Second time staying at Jim’s property and it was just as good as the first time. Great host and great spot!

Stunning 3BR Waterfront Lake Cottage Hottub&Sauna
Amazing host, the dock is separate from the house, a 10 second walk, the hot tub and sauna are in the backyard. Water is very heavy and smells a lot, place is older and has bugs, but overall it was a great stay if you’re not picky. The hosts allowed us an early check in and late check out. Just because of their service I give them a 10/10

*Hot Tub*WoodStove*Firepit*Canoe*Kayaks*Paddlebrds
Perfect retreat spot! We had a few crews working in the area for ice storm clean up and this was the perfect spot to relax at the end of a long working day. Beautiful location and wonderful dockside spots to enjoy the sunsets. Jay is a fantastic host that is very easy to communicate with. Would highly recommend.

Spacious Cottage Escape with Lakeside Hot Tub
Beautiful place to stay. House was perfect for a concert at Casino Rama near by. Would recommend 100%.

Lake Muskoka Classic Cottage w/ Hot Tub
What a dream of a trip to Muskoka! Eight of my friends and I stayed at this lovely cottage and had the most amazing time. The cottage itself is absolutely gorgeous and felt so welcoming, providing the perfect backdrop for our long-overdue get-together. Our host Ashley, was an absolute gem – always quick to respond and incredibly accommodating. We were so touched when they offered us an extra night because of some minor issues that were completely out of their hands. It just shows how much they care about their guests' experience. We're already dreaming of our next visit; this cottage is definitely the place we'll return to!

Spacious family cottage 45 mins from GTA!
Looks better than the pictures!! Beautiful cozy place!!
Pet-friendly cottage rentals

CozyPeaceful LakeCottage HotTub Canada
Sarah was very responsive and accommodating. Very cute living room space with lots of amenities in the kitchen (including a Keurig). Hot tub was a great bonus on an unexpectedly cold weekend in May.

Georgian Bay Cottage - 100 Acres & Private Beach
We had a great time at Patrick’s cottage, the location is great, within walking distance from the beach, it’s exactly as described, very clean and comfortable. Highly recommended.

Charming cottage on Lake Muskoka
Bryan and Pam's cottage is hands down a whopping 10/10. It exceeded my expectations and then some. It truly has everything you need plus more. This place is a true gem! I'm upset I had to leave and it's now booked solid! Book this place, if you can, you will be amazed!

3 Bedroom Waterfront Cottage Kawartha Lakes
Great location , clean cottage , backyard is really nice, with a perfect sunset view. We had a relaxing weekend and would definitely visit again. Special mention to Richard, he is responsive and provided all the required information.

Waterfront 3 BR Cottage 4 Seasons Gravenhurst Heat
I had the pleasure of bringing my cousins from Australia to cottage country. Jonathan was extremely accommodating and providing quick responses when we asked questions prior to and during our stay in Gravenhurst. The cottage had beautiful views of pine lake on the exterior as well as inside in the kitchen and living area. We were really happy with how close shops were as we had to grab a few things we forgot while packing. Would definitely come again.

Baysong Cottage, Hot Tub and Sauna on Georgian Bay
We spent two days in Kathy’s cottage. Great location and perfect for paddlers. Kathy was friendly and responsive for our questions. This cottage has a stunning views even better than the pictures. The only thing I don’t like is that the twelve mile bay road was too bumpy for my mini cooper. We did enjoyed our stay and definitely recommend this property.

Charming waterfront cottage on Lake Simcoe
Great place to stay very clean and comfortable space. Plenty of space to stretch out and enjoy.

Lakefront Cottage with Gorgeous Sunset Views
Such an awesome stay! The cottage was super cozy, clean, and had everything we needed. The lakefront views were even better in person — we spent so much time just hanging out on the deck and by the water. It was the perfect spot to relax and unplug. The hosts were super friendly and made everything really easy. Honestly didn’t want to leave. Definitely coming back!
Private cottage rentals

Hockley valley, up country guest cottage
The cottage is an absolutely paradise! Fere and her wonderful family were consummate hosts - very accommodating and communicative, with great local recommendations. The cabin itself is idyllic and the perfect place for a weekend getaway; we couldn’t believe it was just an hour from the city — we really felt like we got the chance to unplug. The property is beautiful and well-maintained, with great walking trails and gardens! The cottage is comfortable and spacious, with all the necessities for a comfortable and relaxing stay. Thank you so much Fere & Noah!

Beachside Cottages on Lake Muskoka, Three Lakeside
Amazing stay at the cottage by the lake! breakfast with lake's view from the living room, two comfortable bedrooms and one bathroom. surroundings are amazing too with a beautiful trail just 10mn walk from the cottage, and the lake where you can swim and peddle board. the place is a lot cuter than what we expected!

140 Acre Secluded Cottage Retreat 2Br+1 in Muskoka
One of the most beautiful properties I’ve ever stayed at. Matt is great to deal with. The cottage was awesome and Dave the neighbour is super helpful and nice. Don’t be scared of river crossing it was smooth and seamless and made everything even more fun. Matt is a good guy and helpful with anything that comes up. The property is full of hiking trails and has awesome water access, great fishing, beautiful spot for a coffee in the morning. The deck is perfect for watching the sunset and the screen room is a great getaway if a little rain rolls through. All in all I’m extremely pleased with my stay in all aspects. Highly recommend.

Cottage on the Muskoka River
Lana is a wonderful communicator and included a handy info package to help us enjoy our stay. The accomodations were clean and comfortable. The location is quiet and peaceful without being isolated. The process was trouble-free. I would recommend booking here.

Cottage in Tiny
This is a gem find. It was so comfortable and situated 3 minute walk from a beautiful beach. The kitchen was very well equipped the fire pit, the BBQ the outdoor sitting areas were awesome. The beds were comfortable and we slept so well. There is a huge TV with so many channels and content to watch. So easy to settle into a movie after dinner. Very comfortable sitting area. We were 3 adults and we all had space to have some downtime and also to enjoy our company. We would swim and go for 5 km beach walks and drive to very cute small towns and discover the tasty bakeries and cool stores. Everyone we met was so lovely and very relaxed. We had a wonderful time and recommend this pace to everyone. Peaceful, fully equipped, comfortable and 3 minutes from a beautiful beach! What can be better. Thanks Miguel for your clear communications and your helpful suggestions. We had a blast!

Muskoka Dream Cottage
The cottage setting was spectacular! Quiet and peaceful with the amenities my group loves - big, comfortable common spaces, a large kitchen, and rooms for private, peaceful sleeping. The wood burning fireplace was a real treat.

Cozy 2 Bedroom Cottage with beach 5 min walk away!
Very responsive host as this was a last minute booking and she was super accommodating. Great place and convenient location.

Cozy cottage on a private beach / Georgian Bay
We stayed at Ayub’s lovely cottage this holiday season and it was wonderful. Ayub was super friendly and always willing to help and assist, which is super appreciated. Thanks Ayub!
Quick stats about cottage rentals in Midland
Total rentals
40 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
1.8K 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
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- Blue Mountain Village
- Mount St. Louis Moonstone
- Port Carling Golf & Country Club
- Horseshoe Resort
- Osler Bluff Ski Club
- Snow Valley Ski Resort
- Georgian Bay Islands National Park
- Beaver Valley Ski Club
- The Georgian Peaks Club
- Lake Joseph Golf Club
- Muskoka Lakes Golf and Country Club
- Devil's Glen Country Club
- Alpine Ski Club
- National Pines Golf Club
- Muskoka Bay Resort
- The Club At Bond Head
- Craigleith Ski Club
- The Georgian Bay Club
- Rocky Crest Golf Club
- Windermere Golf & Country Club
- South Muskoka Curling and Golf Club
- Barrie Country Club
- Mansfield Ski Club
- Shanty Bay Golf Club
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