Holiday rentals in Penetanguishene

4.92 out of 5 average rating, 301 reviews

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

5 out of 5 average rating, 184 reviews

Tiny home in Waubaushene

Saltbox by the Bay | Vetta/Tay Shore Trail/Bikes

*GUEST BIKES AVAILABLE* Welcome to Saltbox by the Bay, your 4-season escape. A perfect couple's getaway or small family, friends or solo retreat. This vintage cottage is upcycled with luxe amenities. Make delicious meals, play records & boardgames & watch sunsets over the bay. Explore the treats of cottage country: walk or bike the Tay Shore Trail, visit Quayle's Brewery & Wye Marsh, pamper yourself at Vetta Nordic Spa & enjoy one of the nearby towns for beaches, restaurants & local amenities.

4.92 out of 5 average rating, 254 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, 158 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, 94 reviews

Flat 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, 111 reviews

Cottage in Tiny

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.

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 .

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.

4.95 out of 5 average rating, 124 reviews

Flat 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

Cottage in Tiny

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

Superhost

Townhouse in Penetanguishene

4.88 out of 5 average rating, 16 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!

Superhost

Cottage in Midland

4.87 out of 5 average rating, 219 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.

Holiday rentals for every style

Get the amount of space that is right for you

Flats

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Cottages

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A space that's all yours, with room for everyone

Popular amenities for Penetanguishene holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Penetanguishene

4.85 out of 5 average rating, 125 reviews

The Snug Above a Pub

Nicole,JenniferRating, 5 stars1 month ago

Our stay was truly amazing, Courtney was amazing and very helpful when needed. I I highly recommend staying at the Sung above the Pub. super clean everything looked just like the pictures.

Cottage in Penetanguishene

5 out of 5 average rating, 23 reviews

Beautiful & spacious all-season waterfront cottage

DevniRating, 5 stars10 months ago

The place was beautiful and exactly like the pictures. There was plenty of room of group of 8. We were able to use the canoes and also go for a swim as the water near the dock was shallow enough. In the evening, we got a beautiful view of the sunset over Georgian bay while we barbecued and had the gas fire pit going. The place is also close (~15 mins) to a town with some great restaurants we got to try out. The host, Tanya, was very responsive with all the inquires we had. Gave very clear instructions of check in and check out. Great host and stay overall!

4.95 out of 5 average rating, 39 reviews

Bungalow in Midland

Boho Hideaway w/ Hot Tub, Sauna & Games

TianaRating, 5 stars1 week ago

I had a fantastic experience staying here! The place was exactly as described—clean, cozy, and well-decorated. The host was friendly and responsive, and check-in was a breeze. The location is super convenient and close to everything, although it is right near a busy road, so it can get a bit noisy at times. That said, everything else more than made up for it. I’d absolutely stay here again and highly recommend it. Thank you for the lovely stay!

Cottage in Penetanguishene

4.79 out of 5 average rating, 57 reviews

Discovery Retreat: Heated Pool, Hot Tub, Firepit

PaulRating, 5 stars1 month ago

Excellent rental with eveything you need plus some extras. Private and comfortable, perfect for couples or small familes. Hot-tub was a great bonus!

5 out of 5 average rating, 29 reviews

Flat in Midland

Hidden Gem

JoanneRating, 5 stars1 week ago

Truly a hidden gem! The apartment was as described and more - we immediately felt at home. Excellent bed, comfy couch, fully equipped kitchen even nice towels! Loved the outdoor space complete with BBQ. We have marked this as our landing spot when putting our boat on and out of the water in Midland - will be back for sure! Michelle was a very responsive and kind host.

Houseboat in Penetanguishene

4.83 out of 5 average rating, 12 reviews

Float House on Georgian Bay

JosephRating, 5 stars1 month ago

This place is amazing right on the water. What a sunset Thanks, Jessica for allowing me the opportunity to enjoy your Oasis on lake Huron, it's great, keep up the good work.

4.97 out of 5 average rating, 39 reviews

Dome in Tay

The Secret Garden - Dome Escape

MarygraceRating, 5 stars1 week ago

My friends and I stayed at the Secret Garden Dome, and it was truly an unforgettable experience! The dome itself was cozy, stylish, and super unique — definitely a stay to remember. The property was absolutely beautiful and peaceful, set right on a lovely farm surrounded by nature. One of the highlights was getting to meet the ponies and horses — such a sweet and unexpected bonus! Deborah was incredibly friendly and welcoming, which made the stay even more enjoyable. You can really tell they put care into every detail. If you’re looking for a quiet, nature-filled getaway with some serious charm, I highly recommend this place. We had such a great time and would absolutely come back again!