Vacation rentals in Penetanguishene

4.92 out of 5 average rating, 302 reviews

A pristine bathroom countertop is showcased, featuring a sleek white marble surface. Two elegantly bottled toiletries are positioned beside a neatly rolled white towel. Above, a decorative mirror enhances the space, reflecting the soft lighting and serene atmosphere.

Loft in Midland

Perch by the Bay - Downtown Midland / Private Loft

Luxury, Comfort & Georgian Bay Style. This first class rental, "Perch By The Bay", is located in Downtown Midland. Walk everywhere, park your car (free) & enjoy what Midland has to offer. Midland's boat harbour, is only minutes by foot. Live our lifestyle, enjoy our many festivals, professional theatre, artisans, culinary cuisine, etc! It's "sister" AirBnB is "Nest By The Bay" private loft at the rear of the building. 2 night min. preferred, 1 night by request. Not suitable for ages under 6

A private deck area features a small table with two blue chairs on a patterned rug. Potted flowers border the wooden deck, adding a touch of nature. A BBQ grill is positioned nearby, and a large umbrella provides shade.

4.93 out of 5 average rating, 164 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.

The historic Beck House is depicted in this image, showcasing its striking red facade and unique architectural features. A white porch with hanging plants can be seen on the front. The surrounding greenery adds to the charm of the property.

4.92 out of 5 average rating, 255 reviews

The Haunted House Apt 301

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.

4.97 out of 5 average rating, 159 reviews

Home in Penetanguishene

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.

4.91 out of 5 average rating, 95 reviews

An outdoor balcony area features a wooden deck with a green and white patterned rug. Two metal chairs and a glass-top table are arranged for seating. Lush greenery adds a natural element, creating a pleasant outdoor space.

Apartment in Midland

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.

A covered deck is equipped with a round dining table surrounded by white chairs, overlooking a sandy beach and the water. Soft string lights create a gentle ambiance, while chairs invite relaxation. The view extends over Georgian Bay, highlighting the tranquil shoreline.

4.97 out of 5 average rating, 111 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.

A scenic waterfront boardwalk stretches along the calm waters, with a view of a traditional red building and a tall ship docked nearby. Lush greenery frames the scene, contrasting with the bright blue sky. The wooden walkway invites leisurely strolls by the water.

4.99 out of 5 average rating, 78 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 .

A view from the top of a staircase, showcasing a well-lit kitchen area with dark cabinetry and a green countertop. A coffee maker is placed on the counter, and hardwood flooring unites the space leading towards a dining area with red accent wall decor.

4.88 out of 5 average rating, 85 reviews

Quiet & Pristine Georgian Bay Escape near trails

This location is perfect for stays of 28 days or more. Perfect for professionals or students taking semesters. Quiet location 1 block from park on Georgian Bay. Walking distance to town amenities and Host's Irish Pub, Champlain Rotary Trail and Tiny Trails system linking other communities. Entire lower apartment completely refurbished and newly painted. Double car driveway. Completely separate entrance for guests. Also for your use is side patio and a garage for bikes etc.

A dining area features a glass table surrounded by six white chairs. Large sliding glass doors provide access to a wooden deck, revealing a view of the water and surrounding greenery. The space is well-lit by natural light entering from the windows.

4.97 out of 5 average rating, 29 reviews

Georgian Bay Sunset

Enjoy a stylish experience at this centrally located place. Walking distance to all of Penetanguishene’s amenities including the waterfront, walking trails, snowmobile trails, ice fishing, restaurants, grocery, lcbo and much more. From this location you can snowmobile right from the driveway and down to the trails. Enjoy the picturesque view of Georgian Bay and its beautiful sunsets from the deck or inside from the large windows and doors that surround the entire living area.

Guesthouse in Victoria Harbour

A grassy area is framed by two trees, overlooking a sandy beach and water. A picnic table is positioned on the lawn, accompanied by two chairs facing the sunset. The warm light of the setting sun casts long shadows across the scene.

4.97 out of 5 average rating, 260 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

4.95 out of 5 average rating, 125 reviews

A modern electric fireplace is mounted on the wall, featuring realistic flames that gently flicker over a textured surface. The setting is complemented by a cozy seating area nearby, providing an inviting space for relaxation.

Apartment in Midland

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.

4.94 out of 5 average rating, 285 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

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Popular amenities for Penetanguishene vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Penetanguishene

4.88 out of 5 average rating, 42 reviews

A set of decorative dishware is displayed on a white shelf. The collection includes several blue plates and bowls adorned with floral patterns featuring vibrant red roses and delicate blue butterflies. The dishes are stacked neatly, showcasing an inviting design.

Vacation home in Midland

Georgian Bay retreat - apartment in Midland

Superhost

4.9 out of 5 average rating, 52 reviews

A modern retreat on Georgian Bay STRTT-2025-062

Superhost

A serene outdoor area features string lights strung between trees, illuminating the space. Two wooden lounge chairs are positioned on a bed of fallen leaves, facing a large deck that provides a view of the water. The cottage exterior is visible in the background.

5 out of 5 average rating, 7 reviews

Lakeview Cottage

4.8 out of 5 average rating, 45 reviews

Home in Midland

Our vacation home. Fully equipped. Pool. Fire Pit.

5 out of 5 average rating, 14 reviews

A striking black and white photograph of a longhorn cow hangs on the wall, showcasing its prominent horns against a soft, blurred background. The image is framed and positioned above a wooden dining table with dark chairs, contributing to a modern yet rustic dining space.

Townhouse in Midland

Cozy Comfort by the Bay w/Jacuzzi

Cottage in Penetanguishene

5 out of 5 average rating, 23 reviews

Beautiful & spacious all-season waterfront cottage