
House holiday rentals in Midland
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Top-rated house rentals in Midland
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Holiday rentals for every style
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Popular amenities for Midland house rentals
House rentals with a pool

Cute and Cozy House
Anzhelika’s place was great. The house and property were really well-maintained and exactly as described in the listing. She was a very helpful and accommodating host. The location was great, nice and close to downtown and other amenities. My family and I, including two kids under 10, were very happy with the accommodations. I’d definitely recommend staying here

Large 4 Br - 4.5 Bath; Sauna/Heated Pool/2 King
Great stay at Blue Mountain. The kiddos really enjoyed the game room and the pool table. it was also super convenient to be able to schedule free shuttle to pick up and drop off to and from the village. Even if couldn't catch the shuttle it's only 20 min walk.

GreenDream Estate
We had a fantastic stay at Reza’s cottage! The place was spotless, beautifully maintained, and perfectly equipped for a relaxing getaway. Reza was an excellent host—friendly, responsive, and thoughtful. We truly appreciated his hospitality and attention to detail. Highly recommend this charming cottage for a perfect get away. Can’t wait to visit again! Thank you Reza🙏🏻

Blue Mountain Retreat w/ Pool + Village Shuttle
My family and I really enjoyed our stay here. The house is very comfortable. Spacious, clean and very private. Close to Blue Mountain and all it has to offer. The Property Valet team was very quick to respond to communication and attentive. I would definitely stay here again.

Pool Open / Serene mountainside home View/Shuttle
We had a wonderful stay with a family of four including 18 year old teen boys and two dogs. The boys enjoyed the pool table and great tv's while my wife and I enjoyed the great walking and quiet surroundings. It was also easy to have our well trained dogs with us in this location which was wonderful. Thank you Brendan for the terrific stay and allowing us to change our reservation when our plans changed with ease.

Family & Friends Retreat
Peter is a fantastic host—responsive, flexible, and made everything easy. Highly recommend! We had amazing time with family, it was just perfect stay!! Would visit again in summer when pool is operational :)

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 🌎.

Ski, Swim, Soak, Boat & Golf
Had a great time at the cottage. Everything as pictured, beds were comfy, bathrooms clean, and lots to do including games, kayaking, paddle boarding, plunge pool, and hot tub. The lake isn’t great for swimming but we were never at a loss of things to do because of it. Wasaga is also just a drive away if you want something more lively for a night. Herb was a great host and very responsive, friendly and accommodating :)
Weekly house rentals

New Build Luxury - Family Cozy Orillia Home
The only issue was the kettle was t clean and the pots and pans could be updated and other than that beautiful spot and area and wasn’t far from where we wanted to be .

Cozy Home in Barrie
We are extremely happy with our one week stay here while visiting family. The home was clean and well stocked, everything was exactly as described on the listing. The beds were super comfortable. Labeed was always prompt with his responses. No complaints at all about this place and we'd stay here again next time we are in Barrie!

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.

Blue Mountain Home
We stayed at Dianna’s place while we were in Collingwood and the accommodate was even better than the photos! Her place had everything we needed and more. We only stayed a couple nights but it’s set up for long term stays as well. The location was 5 minutes from the water and a 6 minute drive to the downtown core. I would recommend this spot to anyone travelling to Collingwood.

6 Bdrm Lake view, Luxury, Modern Cottage w Hot Tub
Great host with clean and spacious home. Family member accidentally tripped on a door and the owner was happy to communicate on an effective and fair resolution.

Upper Shadow Creek Haven - Waterfront
we had a wonderful stay. squeaky clean,stylish host was very accommodating .defiinetly would stay again.

Dreamy Place in Midland
Farhad is a nice host. Feels like home experience. ♥️

Private Collingwood Home, with acreage & sauna
Erics place was great for the weekend. Just outside of town to keep it a quiet place but close enough so you could go explore collingwood. Sauna is a great addition. Place was clean and had everything you needed for a comfortable stay.
Private house rentals

Luxury Meets Nature at WoodLake - Starlink WiFi
Great location, gorgeous views, and top of the line cottage.

Breathtaking RiverFrontOasis with a HOT Sauna
The best experience, Amanda is an amazing host :)

Sunfilled cottage on the lake
Paige though of ever detail. very clean and well stocked. Paige was very friendly and accommodating. the cottage was very peaceful. The only issue was it was hard to leave and go home! Will be back next year!. Thank you Paige.

Cozy Beachfront Getaway
We had a wonderful stay at the cottage. The best part was the spectacular view of Georgian Bay. The view of the sunrise over the lake was stunning. We enjoyed relaxing on the deck, watching the swans and other birds. We also enjoyed a fire at the waterside fire pit. Not far from the beach or the slopes in winter.

Villa Marina Haven|BBQ|Firepit|Waterfront|Cozy
Fantastic place for big group of people and pets. Bethany is very friendly and responsive which made our check in and out very seamless. Amazing view of Muskoka Lake and we enjoyed the time in the water! Highly recommend this place for a relaxing vacation.

The Turquoise Cottage
Thank you so much Jennifer and Blaine for hosting us! We had a fantastic time. The cottage was adorable and the surroundings were beautiful. Jennifer and Blaine were very responsive and even helped us when we had some car trouble. We loved attending the Vetta Spa which was close by. Highly recommend staying at this cottage! 10/10

Blue Mountain Riverside Lodge | Hottub & Sauna
My husband and I just got back from a much needed relaxing weekend away and the place was perfect! We loved the hot tub and the privacy, including the water fall you can hear. My husband made great use of the sauna. The place was clean and updated. We stayed the whole weekend and found it the perfect place to unwind.

3BR Spacious Home - KING BED
Brigitte's place was amazing! Very beautiful property, very spacious and inviting! Very clean and she has everything labeled which is very helpful! Has everything you could think of and more. We traveled with a group of 4 grown men for a golf trip and it was more than enough space for everyone! Having 2 full bathrooms is a must and the en-suite attached to the master has a beautiful soaker tub. Very beautiful deck with BBQ and comfortable patio furniture and the front yard has a nicely landscaped firepit which we didn't use this time but will next time as we will definitely be back! Great place for families and it is even pet friendly! Brigitte is an amazing host, very attentive and knowledgeable of the surrounding area. Nicest Air BnB I've ever personally stayed at! Solid 9/10
Quick stats about house rentals in Midland
Total rentals
70 properties
Nightly prices starting at
$33 NZD before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
50 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
10 properties have a pool
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
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- Blue Mountain Village
- Port Carling Golf & Country Club
- Osler Bluff Ski Club
- Beaver Valley Ski Club
- Horseshoe Resort
- Devil's Glen Country Club
- Georgian Bay Islands National Park
- Lake Joseph Golf Club
- Muskoka Lakes Golf and Country Club
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- The Club At Bond Head
- Craigleith Ski Club
- The Georgian Peaks Club
- Muskoka Bay Resort
- Rocky Crest Golf Club
- Alpine Ski Club
- Barrie Country Club
- National Pines Golf Club
- Windermere Golf & Country Club
- The Georgian Bay Club
- Muskoka Highlands Golf Links
- South Muskoka Curling and Golf Club
- Mansfield Ski Club