Skip to content

Holiday rentals in Midland

Find and book unique accommodation on Airbnb

When results are available, navigate with the up and down arrow keys or explore by touch or swipe gestures.

Top-rated holiday rentals in Midland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Flat in Penetanguishene
The Haunted House Apt 302
As you pull into the driveway this 1885 Victorian towers above you, your mouth drops in awe of the size. Up the porch to enter a small front door, a dimly lit winding staircase creaks as you ascend to 3rd floor. Original architecture painted many times over oozes with history. 70 years ago the house was turned into apartments, unloved for many of those years, time has definately taken its tole, yet to the spirits within, their big old house still stands proud and distinguished in all its glory.
28 May – 4 JunIndividual Host,
£114 per night
4.88 out of 5 average rating, 365 reviews
Guest favourite
Loft in Midland
Nest By The Bay - Downtown Midland / Private Loft
Luxury, Comfort & Style. This one-of-a-kind rental, "Nest By The Bay", is located in Downtown Midland. Walk everywhere, park your car & enjoy what Midland has to offer. Midland Harbour is only minutes by foot. Live our lifestyle, enjoy our many festivals, professional theatre, artisans, culinary cuisine, seasonal events & so much more! See our other listing "Perch By The Bay", also at this same location. 2 nights min. preferred, 1 night by request. Listing not suitable for ages under 6.
14–21 SeptProfessional Host,
£126 per night
4.88 out of 5 average rating, 283 reviews
Superhost
Home in Midland
The Little Lake House
The Little Lake House can be described as charming, and cozy. Located close to downtown, and a short walk from Little Lake Park, this newly renovated house is a sweet spot for your next stay in Midland. Relax, and read a book in the little backyard. Go out for a scrumptious meal downtown, or choose to stay in, and cook in our airy & bright kitchen. With 2 cozy bedrooms, you'll feel well rested in one of our pillow-top beds.
10–17 JunProfessional Host,
£107 per night
4.84 out of 5 average rating, 168 reviews

Popular amenities for Midland holiday rentals

Stay near Midland's top sights

McDonald's6 locals recommend
Martyrs' Shrine80 locals recommend
Discovery Harbour119 locals recommend
Sainte-Marie Among the Hurons52 locals recommend
The Boathouse Eatery109 locals recommend
Mom's Restaurant19 locals recommend

Other great holiday rentals in Midland

Guest favourite
Cottage in Tiny
Bluestone
28 May – 4 JunIndividual Host,
£140 per night
4.93 out of 5 average rating, 191 reviews
Guest favourite
Flat in Penetanguishene
Church Hill Haven Bed & Breakfast Guest Suite #1
19–26 JulIndividual Host,
£90 per night
4.91 out of 5 average rating, 117 reviews
Guest favourite
Guest house in Victoria Harbour
Sunset Beach Cottage
30 Sept – 7 OctIndividual Host,
£156 per night
4.98 out of 5 average rating, 224 reviews
Guest favourite
Cottage in Port McNicoll
Boe's Cottage: Newly Renovated - Great WIFI
28 Mar – 4 AprIndividual Host,
£145 per night
4.97 out of 5 average rating, 119 reviews
Guest favourite
Cottage in Lafontaine
Beach house (with pool open May-Oct)
5–12 DecIndividual Host,
£93 per night
4.8 out of 5 average rating, 191 reviews
Guest favourite
Dome in Hawkestone
Glen Oro Eco-Retreat Glamping Stargazer Dome
4–11 NovProfessional Host,
£302 per night
4.94 out of 5 average rating, 235 reviews
Superhost
Cottage in Port Severn
Cottage "Down By The Bay"
24–31 DecIndividual Host,
£78 per night
4.86 out of 5 average rating, 127 reviews
Guest favourite
Dome in Bradford West Gwillimbury
Four season glamping dome under the stars
29 Oct – 5 NovIndividual Host,
£108 per night
4.98 out of 5 average rating, 190 reviews
Guest favourite
Home in Penetanguishene
White Rolling Sands of Penetanguishene by theatre
17–24 SeptIndividual Host,
£101 per night
4.97 out of 5 average rating, 143 reviews
Guest favourite
Flat in Midland
Loft By The Bay
14–21 AprProfessional Host,
£60 per night
4.94 out of 5 average rating, 16 reviews
Guest favourite
Flat in Midland
Inn At Little Lake
20–27 AprIndividual Host,
£64 per night
4.98 out of 5 average rating, 64 reviews
Guest favourite
Flat in Midland
Chez Nous Midland
20–27 JulIndividual Host,
£82 per night
4.91 out of 5 average rating, 55 reviews

Quick stats about holiday rentals in Midland

Total rentals

230 properties

Rentals with a pool

20 properties have a pool

Pet-friendly rentals

90 properties allow pets

Family-friendly rentals

150 properties are a good fit for families

Total number of reviews

6.8K reviews

Nightly prices starting at

£16 before taxes and fees

Destinations to explore

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