Vacation rentals in Penetanguishene

4.92 out of 5 average rating, 299 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, 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.

4.88 out of 5 average rating, 460 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.

4.97 out of 5 average rating, 155 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.

4.9 out of 5 average rating, 90 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.

4.97 out of 5 average rating, 106 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 .

An expansive wooden deck overlooks verdant surroundings, featuring a sitting area with four black chairs and a glass table. Large windows enhance natural light and provide views of the forest beyond, creating an inviting space for relaxation.

4.86 out of 5 average rating, 115 reviews

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.

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.

4.96 out of 5 average rating, 26 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.

4.95 out of 5 average rating, 119 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.

A cozy outdoor fire pit area is designed with smooth stones surrounding a crackling fire. Two black wooden chairs provide seating nearby. In the background, a cottage features string lights and large windows, nestled among trees in a serene garden setting.

4.94 out of 5 average rating, 279 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

Townhouse in Penetanguishene

4.87 out of 5 average rating, 15 reviews

Beachfront Retreat - Huge beach/water toys!

Welcome to Rolling Sands Retreat! The Wooded Pine Suite is part of a charming 5-plex located on a spacious property with 270 feet of stunning shoreline. The property feels like a small resort, with the comforts and luxuries of home, featuring brand-new interiors and modern amenities. The large sandy beach is perfect for families with children, and there’s plenty of space for sunbathing!

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Penetanguishene vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Penetanguishene

A sandy beach area features fine, light-colored sand leading to calm, clear waters. The shoreline extends into the distance, bordered by a lush green landscape on the horizon under a clear blue sky.

4.84 out of 5 average rating, 220 reviews

Georgian Bay Cottage - 100 Acres & Private Beach

Chalet in The Blue Mountains

4.96 out of 5 average rating, 202 reviews

Blue Mountain Getaway!

4.88 out of 5 average rating, 113 reviews

Home in Wasaga Beach

2min walk to the beach & 20 min drive to Blue Mnt

4.94 out of 5 average rating, 18 reviews

A spacious backyard area is featured, showcasing a trampoline surrounded by a safety net. A small firepit sits on the grassy ground, accompanied by a canopy tent nearby. The scene is framed by trees and a wooden fence, with a clear blue sky above.

Cottage in Waubaushene

Waubaushene Getaway

5 out of 5 average rating, 10 reviews

Condo in Innisfil

Perfect Comfort 2 Bed ~ BBQ ~ Parking ~ Resort

Condo in The Blue Mountains

The living area features a spacious couch with decorative cushions facing a wall-mounted Smart TV and an electric fireplace. Natural light streams through the large windows with plantation shutters, while a contemporary coffee table rests on the wooden floor. A blue armchair adds a pop of color.

4.65 out of 5 average rating, 54 reviews

Mountainside North Creek Condo w Private Balcony

Apartment in Wasaga Beach

A colorful sign spelling 'WASAGA' is prominently displayed on the beach. The sandy shoreline is visible in the background, with people enjoying the beach under a clear blue sky dotted with clouds. Beach umbrellas and activities can be seen in the distance.

4.82 out of 5 average rating, 11 reviews

Double Waterside Beach Oasis