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Vacation rentals in Penetanguishene

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Penetanguishene

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

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Guest favorite
A spacious living area features a comfortable brown sofa positioned near a glass coffee table. Natural light pours in through large windows with blinds, illuminating a dining area with seating for four. A modern kitchen is visible in the background, equipped with sleek appliances.
Guest suite in Moonstone
4.85 out of 5 average rating, 282 reviews

RELAX @ our HOT TUB and SAUNA in the woods

PLEASE READ! Mt. St. Louis & Horseshoe Valley at doorstep! This is a bright, large and private walk-out GUEST SUITE (basement apartment). Hot tub, patio, fire pit & secluded path in the woods to enjoy nature. Kitchen is equipped with an induction cooktop and all things necessary, even wine bottle opener:) Open concept living room/kitchen/dining room with TV & Roku. Bedroom is a work of Art: dark, mysterious and romantic! Custom Queen bed made from weathered barn wood salvaged from our property.

Top guest favorite
Tiny home in Waubaushene
5 out of 5 average rating, 223 reviews

Saltbox by the Bay/Vetta/4-Season Cottage Escape

Welcome to Saltbox by the Bay, your 4-season escape. Perfect for couples, a small family/friends getaway or solo retreat. This vintage cottage is upcycled with luxe amenities. Made for slow living, play boardgames & classic albums, cook up a storm & watching sunsets over the bay. Explore the charms of cottage country: hike or snowshoe the Tay Shore Trail, visit Quayle's Brewery, pamper yourself at Vetta Nordic Spa, ski/snowboard Moonstone or stop by one of the nearby towns for dinner & bowling.

Top guest favorite
A winterized cottage is surrounded by snow-covered terrain and tall trees. The exterior features large windows and a wraparound deck, offering views of the natural landscape. A black railing lines the deck, and a snow-dusted pathway leads to the entrance.
Cottage in Tiny
4.97 out of 5 average rating, 127 reviews

Cozy Winter Escape - Ski, Hike & Chill by the fire

Insta: @woodwardbythebeach 3min walk to the area’s most beautiful beach, sunsets & trails, you'll be sure to get lost in the serenity of the sand dunes year round Outdoor fire pit- s'mores included! Enjoy the BBQ, deck, & patio; the wine is on us! Fast WIFI for streaming movies or work from cottage Area is secluded yet central. 10min to Midland, close to Balm Beach - arcade, gokart, restaurant, & bar Ski/Hike/Snowmobile then unwind in a peaceful winterized home getaway with indoor fireplace

Top guest favorite
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, 506 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 favorite
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 favorite
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.
Apartment in Midland
4.9 out of 5 average rating, 120 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.

Top guest favorite
A cozy corner features two checkered chairs positioned near a stone hearth. Natural light filters through a large window, highlighting the textured wall. A small table topped with a potted plant adds a touch of greenery, while the warm surroundings evoke a sense of comfort.
Cottage in Victoria Harbour
4.82 out of 5 average rating, 222 reviews

Serenity, Simplicity and Stone

This is a tiny cottage in a sleepy little hollow that opens onto the Georgian Bay. Inside, each stone was carefully chosen and the woodwork was built, piece by piece, by two craftsmen who are highly skilled and passionate about repurposing. It's an art that will leave you in awe; especially if you're worried about climate crisis. The coat hangers are upcycled 100-year-old railway spikes! If you're looking for luxury you will be disappointed but if you're a minimalist you're going to love it.

Guest favorite
A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.
Cottage in Tiny
4.96 out of 5 average rating, 137 reviews

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.

Top guest favorite
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.
Apartment in Midland
4.95 out of 5 average rating, 162 reviews

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.

Guest favorite
A warm living area features a stone fireplace as the focal point, with a cozy fire burning inside. Comfortable leather seating is arranged around a rustic wooden coffee table, complemented by small decorative items and soft textiles, while glass doors lead to another space.
Cottage in Tiny
4.94 out of 5 average rating, 310 reviews

Bluestone

Bluestone is located less than 10 minutes' drive from beautiful Awenda Provincial Park in Tiny, Ontario. Every choice was made with guest comfort in mind. In the Summertime, take a short walk down a wooded path to Georgian Bay and perfect swimming, or explore a hiking trail and take in the natural beauty of the area. In Winter, enjoy skiing and snowshoeing locally, or stay in, put a record on, and cozy up by the fire. License #STRTT-2025-008

Guest favorite
The master bedroom features a spacious bed with a decorative 'RELAX' pillow. Natural light fills the room through a window adorned with dark curtains. Wall art depicting serene landscapes complements the calming neutral tones, while a stylish lamp and small seating area add functional decor.
Loft in Midland
4.89 out of 5 average rating, 382 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. Listing not suitable for ages under 6.

Top guest favorite
A spacious living area features a modern kitchen with stainless steel appliances and light cabinetry. A comfortable sofa is paired with a low coffee table, adorned with greenery. Natural light flows in through large windows, enhancing the inviting space.
Apartment in Coldwater
4.96 out of 5 average rating, 108 reviews

Cozy getaway for two with hot tub!

Unwind in our peaceful guest suite attached to our home located near Mount St-Louis Moonstone, Vetta Nordic Spa and the cozy town of Coldwater. With its private entrance, hot tub (accessible daily between 8am and 10pm) and serene forest surroundings, this space is designed for guests who value calm, quiet and nature. We ask that guests share our appreciation for a tranquil environment.

Popular amenities for Penetanguishene vacation rentals

When is the best time to visit Penetanguishene?

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Frequently Asked Questions

  • 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.

  • 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 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.

  • 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 20 house rentals with wifi 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 10 homes with air conditioning, over 20 homes with a kitchen, over 20 homes with wifi, 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 cottage rentals in Penetanguishene?

    Experience the best of Penetanguishene with our cottage rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Quick stats about vacation rentals in Penetanguishene

  • Total vacation rentals

    Explore 80 vacation rentals in Penetanguishene

  • Nightly prices starting at

    Penetanguishene vacation rentals start at € 17 per night before taxes and fees

  • Verified guest reviews

    Over 3,790 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    70 of Penetanguishene vacation 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