House holiday rentals in Midland

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Popular amenities for Midland house rentals

House rentals with a pool

Guest favourite
Home in Orillia
4.96 out of 5 average rating, 28 reviews

Cute and Cozy House

BrianRating, 5 stars1 week ago
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
Superhost
Home in The Blue Mountains
4.89 out of 5 average rating, 227 reviews

Large 4 Br - 4.5 Bath; Sauna/Heated Pool/2 King

KayeeRating, 5 stars2 weeks ago
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.
Guest favourite
Home in Waubaushene
5 out of 5 average rating, 13 reviews

GreenDream Estate

AnikaRating, 5 stars2 months ago
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🙏🏻
Superhost
Home in The Blue Mountains
4.87 out of 5 average rating, 107 reviews

Blue Mountain Retreat w/ Pool + Village Shuttle

LeaRating, 5 stars6 days ago
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.
Guest favourite
Home in The Blue Mountains
4.95 out of 5 average rating, 196 reviews

Pool Open / Serene mountainside home View/Shuttle

TimRating, 5 stars1 month ago
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.
Guest favourite
Home in Victoria Harbour
4.92 out of 5 average rating, 12 reviews

Family & Friends Retreat

SanginiRating, 5 stars8 months ago
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 :)
Guest favourite
Home in Elmvale
4.89 out of 5 average rating, 19 reviews

Cozy Lakefront Cottage with Hot tub and Pool.

KreenaRating, 5 stars9 months ago
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 🌎.
Superhost
Home in Elmvale
4.88 out of 5 average rating, 76 reviews

Ski, Swim, Soak, Boat & Golf

JessicaRating, 5 stars3 days ago
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

Guest favourite
Home in Orillia
4.93 out of 5 average rating, 29 reviews

New Build Luxury - Family Cozy Orillia Home

SharonRating, 5 stars1 week ago
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 .
Guest favourite
Home in Barrie
4.96 out of 5 average rating, 27 reviews

Cozy Home in Barrie

ShobhaRating, 5 stars1 week ago
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!
Guest favourite
Home in Port McNicoll
5 out of 5 average rating, 8 reviews

Swan Cove Waterfront Retreat

MatthewRating, 5 stars4 months ago
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.
Guest favourite
Home in Collingwood
4.88 out of 5 average rating, 56 reviews

Blue Mountain Home

DeanRating, 5 stars1 week ago
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.
Superhost
Home in Victoria Harbour
4.5 out of 5 average rating, 18 reviews

6 Bdrm Lake view, Luxury, Modern Cottage w Hot Tub

AshanRating, 5 stars1 week ago
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.
Guest favourite
Home in Orillia
4.87 out of 5 average rating, 15 reviews

Upper Shadow Creek Haven - Waterfront

MarceloRating, 5 stars1 month ago
we had a wonderful stay. squeaky clean,stylish host was very accommodating .defiinetly would stay again.
Guest favourite
Home in Midland
4.82 out of 5 average rating, 11 reviews

Dreamy Place in Midland

AjeeshRating, 5 stars8 months ago
Farhad is a nice host. Feels like home experience. ♥️
Guest favourite
Home in Collingwood
4.95 out of 5 average rating, 74 reviews

Private Collingwood Home, with acreage & sauna

CoryRating, 5 stars2 weeks ago
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

Superhost
Home in Bracebridge
4.86 out of 5 average rating, 14 reviews

Luxury Meets Nature at WoodLake - Starlink WiFi

JoshRating, 5 stars2 weeks ago
Great location, gorgeous views, and top of the line cottage.
Superhost
Home in Washago
4.95 out of 5 average rating, 57 reviews

Breathtaking RiverFrontOasis with a HOT Sauna

BahmanRating, 5 stars4 months ago
The best experience, Amanda is an amazing host :)
Top Guest favourite
Home in Gravenhurst
5 out of 5 average rating, 39 reviews

Sunfilled cottage on the lake

RobynRating, 5 stars9 months ago
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.
Superhost
Home in Wasaga Beach
4.67 out of 5 average rating, 9 reviews

Cozy Beachfront Getaway

GaryRating, 5 stars1 month ago
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.
Guest favourite
Home in Port Carling
5 out of 5 average rating, 9 reviews

Villa Marina Haven|BBQ|Firepit|Waterfront|Cozy

Cheuk Him JeffRating, 5 stars2 weeks ago
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.
Superhost
Home in Elmvale
4.84 out of 5 average rating, 31 reviews

The Turquoise Cottage

MadeleineRating, 5 stars4 months ago
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
Superhost
Home in Singhampton
4.92 out of 5 average rating, 25 reviews

Blue Mountain Riverside Lodge | Hottub & Sauna

KristenRating, 5 stars3 weeks ago
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.
Guest favourite
Home in Bond Head
4.94 out of 5 average rating, 54 reviews

3BR Spacious Home - KING BED

TrevorRating, 5 stars3 weeks ago
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

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