Holiday rentals in Penetanguishene

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Top-rated holiday rentals in Penetanguishene

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

Guest favourite

Flat in Penetanguishene

4.88 out of 5 average rating, 374 reviews

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.

26 May – 2 Jun

€ 133 per night
Guest favourite

Flat in Penetanguishene

4.92 out of 5 average rating, 119 reviews

Church Hill Haven Bed & Breakfast Guest Suite #1

A continental breakfast (a fruit, yogurt & baked good) now available for a small extra cost - please give at least 48 hours if you would like this, (need to know allergies & preferences.) or save money & bring your own & prepare in equipped kitchen. Separate basement walkout entrance with own back deck. (The owner lives on the upper level.) There is a queen size bed in the bedroom & a pull-out queen bed in the LR. The toilet & sink are separate from the walk-in shower. BBQ available in summer.

9–16 Jul

€ 72 per night
Guest favourite

Loft in Midland

4.88 out of 5 average rating, 285 reviews

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.

28 Apr – 5 May

€ 147 per night

Popular amenities for Penetanguishene holiday rentals

Stay near Penetanguishene's top sights

Discovery Harbour119 locals recommend
The Boathouse Eatery109 locals recommend
World Famous Dock Lunch36 locals recommend
Phil's Family Restaurant15 locals recommend
Village Square Mall3 locals recommend
Flynn's Irish Pub30 locals recommend

Other great holiday rentals in Penetanguishene

Guest favourite

Flat in Penetanguishene

4.97 out of 5 average rating, 34 reviews

The Sunnyside Stay - 2BD in Midland on 15 acres

27 May – 3 Jun

€ 132 per night
Guest favourite

Flat in Penetanguishene

4.98 out of 5 average rating, 47 reviews

By The Bay spacious one bedroom

23 Feb – 2 Mar

€ 112 per night
Guest favourite

Flat in Midland

4.99 out of 5 average rating, 70 reviews

Inn At Little Lake

15–22 Apr

€ 74 per night
Guest favourite

Flat in Midland

4.91 out of 5 average rating, 58 reviews

Chez Nous Midland

19–26 Aug

€ 95 per night
Guest favourite

Flat in Midland

4.94 out of 5 average rating, 18 reviews

Loft By The Bay

20–27 Aug

€ 123 per night
Guest favourite

Cottage in Penetanguishene

4.95 out of 5 average rating, 21 reviews

Georgian Bay Escape

15–22 Mar

€ 154 per night
Guest favourite

Cabin in Penetanguishene

4.88 out of 5 average rating, 16 reviews

Pet Friendly Nostalgic Cabin

22–29 Jun

€ 171 per night
Guest favourite

Home in Penetanguishene

4.95 out of 5 average rating, 19 reviews

Georgian Bay Water/Beach front Cottage

1–8 Jan

€ 301 per night
Guest favourite

Home in Midland

5.0 out of 5 average rating, 42 reviews

Historic Coach House hosted by John & Donna

7–14 Aug

€ 130 per night
Superhost

Cottage in Penetanguishene

4.81 out of 5 average rating, 27 reviews

Georgian Bay Waterfront Cottage with Sandy Beach

12–19 Jul

€ 791 per night
Superhost

Cottage in Penetanguishene

4.88 out of 5 average rating, 90 reviews

Waterfront Paradise with Sauna and Hottub!

5–12 Apr

€ 834 per night
Guest favourite

Cottage in Tiny

5.0 out of 5 average rating, 22 reviews

The Hideaway Balm Beach Cottage

7–14 May

€ 337 per night

Quick stats about holiday rentals in Penetanguishene

Total rentals

90 properties

Rentals with a pool

10 properties have a pool

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

60 properties are a good fit for families

Total number of reviews

2.7K reviews

Nightly prices starting at

€ 18 before taxes and fees

Destinations to explore

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