
Holiday houses in Penetanguishene
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Top-rated holiday rentals in Penetanguishene
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

White Rolling Sands of Penetang by Theatre
Shores of Georgian Bay - enjoy a firepit in the backyard of a deep lot backing onto woods with trails. Local walking and cycling routes, vege and flower gardens from private sunny back deck. Fully licensed and located close to Kings' Wharf Theatre / Discovery Harbour. Experience the natural beauty of Tiny Beaches, Georgian Bay Islands N.P and Awenda P.P. nearby (Park pass available for use). Marinas, beaches, boat cruise of the islands, Ste Marie Among the Hurons and Wye Marsh (Midland) nearby.

Loft By The Bay
Welcome to our charming second storey apartment in downtown Midland, Ontario. This cozy space features a bedroom, office with futon, full kitchen, bathroom, laundry, and a bright open concept living area. Enjoy easy access to local shops, restaurants, and attractions. Explore the picturesque waterfront and nearby hiking trails. Retreat to this comfortable and inviting apartment after a day of work or play. Book your stay today for a convenient, comfortable, and memorable experience in Midland.

Ultimate Georgian Bay Vacation Getaway
Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

By The Bay spacious one bedroom
This unique place has a style all its own and only steps away from , beaches , water front dining and theater! With all the amenities of home you'll be comfortable to stay for the weekend or extended stays. Fully equipped kitchen with convection oven , dishwasher , microwave, keurig coffee maker and built in washer/ dryer . Spacious bathroom with an over sized walk in shower . And to end the day enjoy the full sized bed room and closet to unpack luggage with a queen size Endy foam mattress .

The Bay View Cottage w/hot tub
Welcome to our 4 season, 2 family cottage with Georgian Bay views and a hot tub. 3 min walk to the cutest small beach that has stunning sunsets, 12 min to Awenda Provincial Park which has great hiking, beaches, biking and winter activities. Short drive to Balm Beach. Downtown Midland has great restaurants and everything a quaint downtown has to offer. Winter has so much to offer including ice fishing, OFSC snowmobile trails, cross country skiing and much more. Max occupancy is 8 adult.

Secluded Lakeside Retreat - Atkins Hideaway
Tucked in the heart of Muskoka, this handcrafted timber frame cabin rests alongside a scenic spring-fed lake, surrounded by 8 acres of private forest. Only 10 minutes from Bracebridge, enjoy serene lake life and natural beauty while remaining close to town amenities, local shops, and eateries. Enjoy private dock relaxation, cozy cabin comforts, and outdoor fires. A Provincial Park Day Pass is included (*security deposit required) for added adventure. Come relax, recharge and reconnect.

Glass Dome - Sleep Under The Stars- Free Sundays
Discover this new, stunning 22ft Glass Geodesic Dome nestled in the heart of Uxbridge. Imagine waking up surrounded by 360-degree panoramic views of the natural landscape Please note... its FULL WEEKEND STAYS ONLY - BOOK FRIDAY AND SATURDAY-SUNDAY IS FREE. This allows guests to fully enjoy their Sunday without feeling rushed to check out at 11am. Enjoy all day Sunday with option of staying the evening. 8X12 BUNKIE NOW AVAIL. SLEEPS 4 $100/NIGHT ( 2 bunk beds)

Sunset Beach Cottage
Part log treehouse, part beach house and 100% of what you need to enjoy a peaceful getaway only 1.5 hours from Toronto! Walk up the private staircase and pause to enjoy the spectacular treetop and waterfront views from your own wraparound deck before entering your 900 sq. ft. oasis. Enjoy access to your own lawn, picnic table and beach* area and all that Georgian Bay and the area has to offer. *water levels fluctuate Insta: sunset_beach_cottage_canada

Hosted by Nous Midland
Small-town charm at its best! Our centrally located apartment is the perfect home base for your small-town adventures. We're minutes from the unique shops and restaurants in downtown Midland and the Midland Harbour. There is plenty to experience; attend a local festival, take in a tourism site, hop onto the Trans Canada Trail System with your bike or snowmobile, attend a show/concert at the Midland Cultural Centre, or snowshoe through the Wye Marsh.

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. Listing not suitable for ages under 6.

A-Frame hidden in forest Muskoka, Georgian Bay
Welcome to our A-frame /Triangle House, Wifi, Sauna, Kitchen, A/C, Free Parking, King Bed, FIFA friendly, Smart Tv, Peaceful, Social Media Favourite, Top Choice for city escape, and an ideal weekend getaway. Come heal, enjoy the light luxury in nature, and enjoy the slow living at this premium vacation experience. Rare architecture, designer cabin. Come and gather energy in this forest sanctuary.
Popular amenities for Penetanguishene holiday rentals
Stay near Penetanguishene's top sights
Other great holiday rentals in Penetanguishene

Waterfront Cottage in Muskoka | SAUNA | Beach

A modern retreat on Georgian Bay STRTT-2026-089

Rustic Muskoka Bunkie | Fire Pit, Nearby Beach

Lakeside Stunning Cottage - Private Beach - New

Lakefront Sauna Winter Escape

The Beach Deck Retreat

3BR Townhome – Wright Dr Midland Near Little Lake

Quiet & Pristine Georgian Bay Escape near trails
When is the best time to visit Penetanguishene?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $153 AUD | $149 AUD | $151 AUD | $183 AUD | $205 AUD | $187 AUD | $229 AUD | $231 AUD | $192 AUD | $175 AUD | $150 AUD | $171 AUD |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 12°C | 17°C | 20°C | 19°C | 15°C | 9°C | 3°C | -3°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Penetanguishene?
Penetanguishene has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Penetanguishene?
Experience the best of Penetanguishene with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
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 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.
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 cottage rentals in Penetanguishene have air conditioning?
Absolutely! We offer over 20 cottage rentals with air conditioning in Penetanguishene. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Penetanguishene have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Penetanguishene. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Penetanguishene have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Penetanguishene. Enjoy a tailored experience with all the comforts you desire.
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.
What are the most popular amenities for House Rentals in Penetanguishene?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 10 homes with air conditioning, over 20 homes with a kitchen, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Penetanguishene

Total holiday rentals
Explore 80 holiday rentals in Penetanguishene

Nightly prices starting at
Penetanguishene holiday rentals start at $28 AUD per night before taxes and fees

Verified guest reviews
Over 3,480 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 30 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
70 of Penetanguishene holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Penetanguishene rentals

4.8 Average rating
Penetanguishene stays are highly rated by guests—averaging 4.8 out of 5!
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- Family-friendly rentals Penetanguishene
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- House rentals Penetanguishene
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- Pet-friendly rentals Penetanguishene
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- Rentals with a patio Penetanguishene
- Rentals with a fireplace Penetanguishene
- Beachfront rentals Penetanguishene
- Rentals with lake access Penetanguishene
- Blue Mountain Village
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Beaver Valley Ski Club
- Wasaga Beach Area
- Osler Bluff Ski Club
- Devil's Glen Country Club
- The Ridge at Manitou Golf Club
- Three Mile Lake
- Georgian Bay Islands National Park
- Scandinave Spa Blue Mountain
- Kee To Bala
- Torrance Barrens Dark Sky Conservation Area
- Taboo Muskoka Resort & Golf
- Burl's Creek Event Grounds
- Innisfil Beach Park
- Bass Lake Provincial Park
- Awenda Provincial Park
- Casino Rama Resort
- Wye Marsh Wildlife Centre
- Menominee Lake
- Orillia Opera House
- Centennial Beach
- Couchiching Beach Park




