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Holiday rentals in Penetanguishene

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Penetanguishene

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

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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.
Flat in Penetanguishene
4.9 out of 5 average rating, 535 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, 171 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.

Top guest favourite
A modern kitchen features natural wood cabinetry and a large marble countertop island with seating. Stainless steel appliances, including an electric stove and refrigerator, are visible. The space is well-lit with recessed lighting, and decorative plants add a touch of warmth.
Flat in Midland
4.91 out of 5 average rating, 143 reviews

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.

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, 269 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
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.
Flat 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
A quaint blue cottage features a welcoming front deck with two yellow chairs facing the lush green lawn. The cottage is surrounded by trees and showcases large windows that bring natural light into the interior.
Tiny home in Waubaushene
5 out of 5 average rating, 250 reviews

Saltbox by the Bay | Views, Bikes, Vetta Spa

*MAY AVAILS* *GUEST BIKES* Welcome to Saltbox by the Bay, a cozy vintage cottage with luxe amenities & beautiful views. Perfect as a couples getaway, small family/friends vacation or solo retreat. Ease into slow living with indoor or outdoor fires, cook your favourite meals, play boardgames & albums, as you watch birds & sunsets over the bay. Enjoy nearby excursions: walk or bike the Tay Shore Trail, visit Quayle's Brewery, Vetta Nordic Spa & explore charming towns around Georgian Bay.

Top guest favourite
A handcrafted timber frame cabin is set among trees, featuring natural wood siding and large windows that invite the outdoors in. A welcoming porch is accessed by a wooden staircase, while a covered area to the side provides shelter. The surrounding forest complements the rustic design.
Cabin in Bracebridge
5 out of 5 average rating, 267 reviews

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.

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.
Guest house in Victoria Harbour
4.96 out of 5 average rating, 291 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

Top guest favourite
A modern garage apartment is displayed, featuring a neutral-toned exterior with a large garage door and a side entrance. A spacious driveway is visible, providing ample parking space. The entrance is highlighted by a white door, and trees are partially visible in the background.
Flat in Midland
4.94 out of 5 average rating, 195 reviews

Chez 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.

Guest favourite
An outdoor fire pit surrounded by gravel is present, featuring two wooden chairs. A hot tub is located nearby, positioned in front of a geodesic dome with large windows. String lights are draped overhead, illuminating the outdoor space.
Dome in Utopia
4.96 out of 5 average rating, 180 reviews

Glamping Dome Riverview Utopia

Come retreat into nature at the Riverview Glamping Dome… a 4 season getaway located on Rustic Roots Farm and Eco-retreat 1 hour north of Toronto. Whether you're looking for a romantic getaway or to come disconnect from the hustle and bustle of everyday life this geodesic dome is for you! Located on 64 sprawling acres come explore hiking trails, go fishing, relax in the hot tub, and stargaze fireside.

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, 155 reviews

A-Frame Hidden in the 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.

Guest favourite
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, 252 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?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$151 SGD$142 SGD$123 SGD$165 SGD$185 SGD$168 SGD$207 SGD$208 SGD$174 SGD$158 SGD$135 SGD$154 SGD
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 $51 SGD 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    70 of Penetanguishene holiday rentals include wifi 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