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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.

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Guest favourite
The image captures a tranquil hot tub filled with clear water, positioned on a deck overlooking Georgian Bay. A soft sunset casts a warm glow across the sky, and the silhouettes of a gazebo and dock are visible in the background.
Home in Meaford
4.87 out of 5 average rating, 521 reviews

Beach House Hideaway by Post Office Motel *HOT TUB

This beach house was designed with relaxation and the enjoyment of togetherness in mind. Let your worries melt away as you slip into the warmth of this water side hot tub featuring stunning view across Georgian Bay and up the mountain side, as fresh snow falls around you. The open concept design makes this the perfect place to gather with family and friends w/ walkout waterfront patio and dock access for swimming. 2 min to downtown Meaford, 20 min to Blue Mtn, 1.5 hrs to Tobermory. Hiking Trails

Top Guest favourite
The historic Beck House, a striking Victorian structure, stands with a distinctive red façade and slate roof. A spacious porch with white railings invites guests, while the well-kept lawn adds to its charm. A wooden sign identifies the property, blending history with a warm welcome.
Apartment in Penetanguishene
4.89 out of 5 average rating, 533 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.

Top Guest favourite
A vibrant garden showcases a variety of colorful flowers, with a prominent rock identified by the number 14. Lush greenery surrounds the area, adding to the inviting outdoor space in front of a brick house. Well-maintained lawns complement the floral displays.
Home in Penetanguishene
4.97 out of 5 average rating, 170 reviews

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.

Guest favourite
A spacious glamping dome is nestled among lush green trees, showcasing large windows and a triangular design. The entrance is framed by rustic outdoor seating, and soft lighting emanates from inside, creating an inviting atmosphere amidst the surrounding foliage.
Dome in Utopia
4.95 out of 5 average rating, 266 reviews

Off-grid Glamping Dome Nestled in the Woods

Welcome to our private campsite in Utopia, ON. Our family’s glamping dome is your chance to experience a unique getaway surrounded by the sights & sounds of nature. Amenities include camping essentials & some glamping perks: king size bed, bbq, fireplace, Indoor incineration toilet, soap & water, outdoor shower (summer only), kettle, cooking utensils. Nearby is Purple Hill Lavender Farms, Drysdale's Tree Farm, Tiffin Conservation Area, Nottawasaga & golf courses. Wasaga Beach is 30 min away.

Top Guest favourite
Cabin in Huntsville
4.95 out of 5 average rating, 585 reviews

Aux Box Muskoka | Boutique | Private Nordic Spa

Escape to the Aux Box, a boutique luxury cabin nestled in the Muskoka woods with serene river views. Designed for comfort and style, it features in-floor heating, custom cabinetry, and premium amenities. Step into your private Nordic Spa with a sauna, hot tub, and cold plunge for the ultimate relaxation. Enjoy total seclusion while being less than 10 minutes from the shops, dining, and charm of downtown Huntsville. COMING SOON: waterfront access with private dock, lounge chairs and a canoe.

Top Guest favourite
A charming two-story house is captured against a clear blue sky. The exterior features horizontal grey siding, wooden accents, and a balcony above the entrance. A stone facade frames the lower part of the structure, while a garage door adds to the home's appeal.
Apartment in Penetanguishene
4.99 out of 5 average rating, 102 reviews

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 .

Top Guest favourite
An exterior view of a modern black tiny house is depicted, surrounded by trees and natural foliage. Two sets of stairs lead to the entrance, with a gravel pathway visible. Window placements create a unique design, and soft lighting illuminates the scene against the evening sky.
Home in Gravenhurst
4.98 out of 5 average rating, 216 reviews

Woodland Muskoka Tiny House

Enjoy the sounds of nature when you stay in this unique tiny house. This 600 sq ft home is nestled amongst 10 acres of towering trees, granite rock and trails to explore. The tiny home will not feel so tiny once inside. With high ceilings, plenty of windows, and surprisingly spacious rooms - it is the perfect hideaway for those wanting to unplug in Muskoka. The three season, screened in porch invites you to enjoy your coffee (or wine!) in nature without being bothered by the mosquitos!

Guest favourite
The geodesic dome features a modern white exterior, set against a backdrop of trees. A wooden deck extends from the dome, leading to a covered gazebo, with a pathway of wood chips guiding the approach. Soft sunlight filters through the branches, creating a serene atmosphere.
Dome in Uxbridge
4.84 out of 5 average rating, 103 reviews

The Bubble Glamping Dome

Escape to a luxury geodesic dome on our scenic farm, nestled at the edge of the forest. Fully equipped with heating, cooling, a private washroom, deck, and hot tub, it’s the perfect blend of comfort and nature. Explore the farm, meet our sheep, chickens, and livestock guardian dog, or hike over 100 acres of connected regional forest. Whether you’re relaxing under the stars or adventuring outdoors, this unique glamping retreat promises an unforgettable experience.

Top Guest favourite
Two wooden Adirondack chairs are positioned on a lush green lawn facing the water, framed by overhanging tree branches. The sunset creates a colorful display on the horizon, reflecting on the calm surface of the lake, while a small table holds a wine bottle and glasses.
Guesthouse in Victoria Harbour
4.96 out of 5 average rating, 288 reviews

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

Guest favourite
A secluded treehouse is nestled among tall trees, showcasing a modern design featuring large windows and a sloped roof. The structure is elevated, supported by solid timber, and surrounded by fallen leaves, highlighting the natural beauty of the forested setting.
Treehouse in Dorset
4.96 out of 5 average rating, 303 reviews

Raven's Roost- private luxury treehouse with sauna

Unplug your tech and let the sights and sounds of the forest be your muse. Treat your body to the healing powers of a eucalyptus sauna. Cool down in the outdoor shower, stargaze, crack a book, play some Scrabble, colour or write. Sing with the wolves, skate through the forest, canoe, climb, swim, ski or snowmobile from your door to the OFSC trail. The quaint town of Dorset is in the center of one if Canada's most impressive landscapes. Escape. Exhale.

Top Guest favourite
The exterior of the A-frame home is showcased, featuring a striking black facade and tall triangular roof. Large windows illuminate the interior, and a spacious wooden deck extends across the front, surrounded by lush greenery that encapsulates the natural setting.
Home in Georgian Bay
4.97 out of 5 average rating, 152 reviews

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.

Superhost
A dining area features a round table surrounded by six white chairs, complemented by a decorative plant. A glass-front cabinet displays glassware. A cozy seating area with a brown couch is visible in the background, accented by a light-colored wall and framed artwork.
Cottage in Midland
4.87 out of 5 average rating, 250 reviews

House on the Hill, HotTub, Relaxation, Bike Trails

Experience the perfect blend of historic charm and modern comfort in this century home. Bask in the refreshing breeze from Georgian Bay and enjoy the tranquility it brings. Explore nearby downtown shops, take advantage of the Trans Canada Trail for walking, running or biking, and discover a variety of local attractions just minutes away.

Popular amenities for Penetanguishene holiday rentals

When is the best time to visit Penetanguishene?

MonthJanFebMarAprMayJuneJulyAugSeptOctNovDec
Avg. price$163 AUD$153 AUD$132 AUD$178 AUD$200 AUD$182 AUD$224 AUD$225 AUD$188 AUD$171 AUD$146 AUD$167 AUD
Avg. temp-7°C-6°C-1°C6°C12°C17°C20°C19°C15°C9°C3°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 $70 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 40 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 30 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 apartment rentals in Penetanguishene have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Penetanguishene. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Penetanguishene have a kitchen?

    Absolutely! We offer over 10 apartment 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 house rentals in Penetanguishene have free parking?

    Absolutely! We offer over 20 house 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 free parking, over 20 homes with a kitchen, over 20 homes with wifi, over 10 homes with air conditioning, 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 $55 AUD per night before taxes and fees

  • Verified guest reviews

    Over 3,340 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 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!

Destinations to explore

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