Cottage vacation rentals in Midland

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Popular amenities for Midland cottage rentals

Cottage rentals with a hot tub

Guest favorite
Cottage in Bracebridge
4.93 out of 5 average rating, 105 reviews

Waterfront cottage on quiet Spence lake

SarahRating, 5 stars1 month ago
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.
Superhost
Cottage in Brechin
4.77 out of 5 average rating, 137 reviews

Beautiful Four Bedroom Lagoon City Waterfront Home

EilidhRating, 5 stars8 months ago
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!
Superhost
Cottage in Bala
4.86 out of 5 average rating, 148 reviews

Muskoka Waterfront Cottage - HOT TUB & SAUNA

ZachRating, 5 stars2 weeks ago
Second time staying at Jim’s property and it was just as good as the first time. Great host and great spot!
Superhost
Cottage in Gravenhurst
4.86 out of 5 average rating, 185 reviews

Stunning 3BR Waterfront Lake Cottage Hottub&Sauna

KamyarRating, 5 stars4 weeks ago
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
Guest favorite
Cottage in Bracebridge
4.94 out of 5 average rating, 219 reviews

*Hot Tub*WoodStove*Firepit*Canoe*Kayaks*Paddlebrds

DaleRating, 5 stars3 weeks ago
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.
Guest favorite
Cottage in Orillia
4.94 out of 5 average rating, 116 reviews

Spacious Cottage Escape with Lakeside Hot Tub

reneeRating, 5 stars3 weeks ago
Beautiful place to stay. House was perfect for a concert at Casino Rama near by. Would recommend 100%.
Guest favorite
Cottage in Port Carling
4.95 out of 5 average rating, 168 reviews

Lake Muskoka Classic Cottage w/ Hot Tub

MoniqueRating, 5 stars1 week ago
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!
Guest favorite
Cottage in Innisfil
4.86 out of 5 average rating, 137 reviews

Spacious family cottage 45 mins from GTA!

AndrianRating, 5 stars1 week ago
Looks better than the pictures!! Beautiful cozy place!!

Pet-friendly cottage rentals

Top guest favorite
Cottage in Severn Bridge
5 out of 5 average rating, 143 reviews

CozyPeaceful LakeCottage HotTub Canada

KatieRating, 5 stars1 day ago
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.
Superhost
Cottage in Tiny
4.84 out of 5 average rating, 220 reviews

Georgian Bay Cottage - 100 Acres & Private Beach

SebastianRating, 5 stars31 months ago
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.
Guest favorite
Cottage in Bracebridge
4.92 out of 5 average rating, 200 reviews

Charming cottage on Lake Muskoka

DanielleRating, 5 stars3 days ago
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!
Superhost
Cottage in Brechin
4.84 out of 5 average rating, 102 reviews

3 Bedroom Waterfront Cottage Kawartha Lakes

ShikhaRating, 5 stars1 week ago
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.
Guest favorite
Cottage in Gravenhurst
4.88 out of 5 average rating, 130 reviews

Waterfront 3 BR Cottage 4 Seasons Gravenhurst Heat

DanielaRating, 5 stars5 days ago
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.
Superhost
Cottage in MacTier
4.91 out of 5 average rating, 106 reviews

Baysong Cottage, Hot Tub and Sauna on Georgian Bay

SijiaoRating, 5 stars2 weeks ago
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.
Top guest favorite
Cottage in Innisfil
4.98 out of 5 average rating, 130 reviews

Charming waterfront cottage on Lake Simcoe

JeremyRating, 5 stars2 weeks ago
Great place to stay very clean and comfortable space. Plenty of space to stretch out and enjoy.
Superhost
Cottage in Brechin
4.85 out of 5 average rating, 108 reviews

Lakefront Cottage with Gorgeous Sunset Views

AlianaRating, 5 stars1 month ago
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

Top guest favorite
Cottage in Palgrave
4.99 out of 5 average rating, 211 reviews

Hockley valley, up country guest cottage

KateRating, 5 stars1 week ago
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!
Guest favorite
Cottage in Milford Bay
4.95 out of 5 average rating, 38 reviews

Beachside Cottages on Lake Muskoka, Three Lakeside

AnouckRating, 5 stars7 months ago
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!
Top guest favorite
Cottage in MacTier
5 out of 5 average rating, 17 reviews

140 Acre Secluded Cottage Retreat 2Br+1 in Muskoka

ChristianRating, 5 stars1 month ago
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.
Guest favorite
Cottage in Bracebridge
4.89 out of 5 average rating, 489 reviews

Cottage on the Muskoka River

JayRating, 5 stars1 week ago
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.
Guest favorite
Cottage in Tiny
5 out of 5 average rating, 12 reviews

Cottage in Tiny

AnnellieRating, 5 stars9 months ago
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!
Superhost
Cottage in Gravenhurst
4.86 out of 5 average rating, 140 reviews

Muskoka Dream Cottage

EarleenRating, 5 stars7 months ago
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.
Guest favorite
Cottage in Innisfil
4.92 out of 5 average rating, 13 reviews

Cozy 2 Bedroom Cottage with beach 5 min walk away!

JeannineRating, 5 stars1 month ago
Very responsive host as this was a last minute booking and she was super accommodating. Great place and convenient location.
Guest favorite
Cottage in Tiny
4.83 out of 5 average rating, 35 reviews

Cozy cottage on a private beach / Georgian Bay

DéboraRating, 5 stars5 months ago
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

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Simcoe County
  5. Midland
  6. Cottage rentals