Vacation rentals in Penetanguishene

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Top-rated vacation rentals in Penetanguishene

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

Guest favorite

Apartment 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.

May 26 – Jun 2

ﺩ.ﺇ471 per night
Guest favorite

Apartment 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.

Jul 9 – 16

ﺩ.ﺇ244 per night
Guest favorite

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.

Apr 28 – May 5

ﺩ.ﺇ558 per night

Popular amenities for Penetanguishene vacation 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 vacation rentals in Penetanguishene

Guest favorite

Apartment in Penetanguishene

4.97 out of 5 average rating, 34 reviews

The Sunnyside Stay - 2BD in Midland on 15 acres

May 27 – Jun 3

ﺩ.ﺇ452 per night
Guest favorite

Apartment in Penetanguishene

4.98 out of 5 average rating, 47 reviews

By The Bay spacious one bedroom

Feb 23 – Mar 2

ﺩ.ﺇ371 per night
Guest favorite

Apartment in Midland

4.99 out of 5 average rating, 70 reviews

Inn At Little Lake

Apr 15 – 22

ﺩ.ﺇ278 per night
Guest favorite

Apartment in Midland

4.91 out of 5 average rating, 58 reviews

Chez Nous Midland

Aug 19 – 26

ﺩ.ﺇ312 per night
Guest favorite

Apartment in Midland

4.94 out of 5 average rating, 18 reviews

Loft By The Bay

Aug 20 – 27

ﺩ.ﺇ419 per night
Guest favorite

Cottage in Penetanguishene

4.95 out of 5 average rating, 21 reviews

Georgian Bay Escape

Mar 15 – 22

ﺩ.ﺇ511 per night
Guest favorite

Cabin in Penetanguishene

4.88 out of 5 average rating, 16 reviews

Pet Friendly Nostalgic Cabin

Jun 22 – 29

ﺩ.ﺇ571 per night
Guest favorite

Home in Penetanguishene

4.95 out of 5 average rating, 19 reviews

Georgian Bay Water/Beach front Cottage

Jan 1 – 8

ﺩ.ﺇ994 per night
Guest favorite

Home in Midland

5.0 out of 5 average rating, 42 reviews

Historic Coach House hosted by John & Donna

Aug 7 – 14

ﺩ.ﺇ463 per night
Superhost

Cottage in Penetanguishene

4.81 out of 5 average rating, 27 reviews

Georgian Bay Waterfront Cottage with Sandy Beach

Jul 12 – 19

ﺩ.ﺇ3,047 per night
Superhost

Cottage in Penetanguishene

4.88 out of 5 average rating, 90 reviews

Waterfront Paradise with Sauna and Hottub!

Apr 5 – 12

ﺩ.ﺇ3,149 per night
Guest favorite

Cottage in Tiny

5.0 out of 5 average rating, 22 reviews

The Hideaway Balm Beach Cottage

May 7 – 14

ﺩ.ﺇ1,162 per night

Quick stats about vacation 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

ﺩ.ﺇ73 before taxes and fees

Frequently Asked Questions

  • Do cottage rentals in Penetanguishene have a kitchen?

    Absolutely! We offer over 20 cottage rentals with a kitchen in Penetanguishene. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Penetanguishene?

    Yes! Work meets play with ease at over 40 vacation rentals in Penetanguishene featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do cottage rentals in Penetanguishene have free parking?

    Absolutely! We offer over 20 cottage rentals with free parking in Penetanguishene. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Penetanguishene have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Penetanguishene. Enjoy a tailored experience with all the comforts you desire.

  • Are there pet-friendly vacation rentals in Penetanguishene?

    Four-legged friends are welcome in Penetanguishene. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Are there Penetanguishene vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Penetanguishene, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Penetanguishene have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Penetanguishene. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Cottage Rentals in Penetanguishene?

    Enhance your stay in our Cottage Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with free parking, over 20 homes with wifi, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there family-friendly vacation rentals in Penetanguishene?

    Penetanguishene has more than 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in apartment rentals in Penetanguishene?

    Experience the best of Penetanguishene with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Destinations to explore

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