Holiday houses 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

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, 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.

4.88 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.

4.96 out of 5 average rating, 27 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

4.97 out of 5 average rating, 259 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, 124 reviews

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.

4.97 out of 5 average rating, 228 reviews

Cottage in Torrance

Beautiful Nine Mile Lake

Beautiful Muskoka getaway! Modern 4 season waterfront cottage! Stunning views! Located on picturesque Nine Mile Lake. Over 70% of the lake is crown land. Perfect for kayaking and canoeing to enjoy all the beauty Muskoka is known for. We have kayaks a canoe and a paddle board for you to enjoy. Plenty of sun exposure on the dock you can swim all day long. Close to hiking and snowmobile trails. May 15-Oct 2 Minimum 6 nights with a Sunday check in.

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

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Popular amenities for Penetanguishene holiday rentals

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Pool

Free parking on premises

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Other great holiday rentals in Penetanguishene

Superhost

Cottage in Tiny

4.9 out of 5 average rating, 52 reviews

A modern retreat on Georgian Bay STRTT-2025-062

KaterynaRating, 5 stars5 months ago

Beautiful home! We absolutely loved the living area. It felt cozy with all the natural light coming in through the ceiling windows. The dining area was great on a snowy day. We played the games and enjoyed the views of the snow-covered pine trees! Loved the location and the house. Would recommend!

Superhost

Cottage in Penetanguishene

4.82 out of 5 average rating, 51 reviews

Georgian Bay Waterfront Cottage with Sandy Beach

John EdisonRating, 5 stars8 months ago

Alexandra was the perfect host. Very responsive, considered and even accommodated to all the needs we had. she allowed us to have a beautiful gathering with some extra friends that came for a celebration of our engagement (not staying at night). It was a lovely place, full of small details that enriched our experience, highly recommend this place.

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!