
Vacation rentals in Penetanguishene
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Top-rated vacation rentals in Penetanguishene
Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

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.

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

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.

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.

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.

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.

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.

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.

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

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.

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
Stay near Penetanguishene's top sights
Other great vacation rentals in Penetanguishene

Georgian Bay retreat - apartment in Midland

King Bed, Pool, Gym, Ravine View, Your Getaway!

Waterfront Muskoka guest suite near Casino Rama

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

Georgian Bay Escape

Spacious Apartment Facing The Severn River

Luxury Cottage - The Lookout. Next to Balm Beach

3BR Townhome – Wright Dr Midland Near Little Lake
When is the best time to visit Penetanguishene?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 94 | € 91 | € 93 | € 112 | € 126 | € 115 | € 141 | € 142 | € 118 | € 158 | € 103 | € 104 |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 12°C | 17°C | 20°C | 19°C | 15°C | 9°C | 3°C | -3°C |
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!
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- Blue Mountain Village
- Snow Valley Ski Resort
- Cobble Beach Golf Resort Community
- Beaver Valley Ski Club
- Devil's Glen Country Club
- Osler Bluff Ski Club
- Craigleith Ski Club
- Rocky Crest Golf Club
- Mount St. Louis Moonstone
- Port Carling Golf & Country Club
- The Ridge at Manitou Golf Club
- The Georgian Peaks Club
- Muskoka Lakes Golf and Country Club
- The Club At Bond Head
- Windermere Golf & Country Club
- Muskoka Bay Resort
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- The Georgian Bay Club
- Georgian Bay Islands National Park
- Barrie Country Club
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