Book Holiday Homes in Penetanguishene

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Featured Holiday Homes in Penetanguishene

Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage

Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage

Victoria Harbour ON
Stay at this holiday home in Tay. Enjoy a garden, laundry facilities and air conditioning. Popular attractions Waubaushene Beaches Provincial Park and Tay Township ...
Opens in a new windowUp to 40% SALE Near-Skiing-Mount Gorgeous Cottage
A-Frame Escape in the Woods of Georgian Bay, Muskoka

A-Frame Escape in the Woods of Georgian Bay, Muskoka

Georgian Bay ON
The price is NZ$879 per night from 11 May to 12 May
NZ$879
11 May - 12 May
includes taxes & fees
Stay at this holiday home in Georgian Bay. Enjoy free Wi-Fi, patios and cable/satellite TV service. Popular attractions Kelleher Island and Vanomi Island are ...
Opens in a new windowA-Frame Escape in the Woods of Georgian Bay, Muskoka
VILLA UPPER & LOWER SPECIAL RATES SLEEPS 15, VERY CLOSE TO BEACH ACCESS,

VILLA UPPER & LOWER SPECIAL RATES SLEEPS 15, VERY CLOSE TO BEACH ACCESS,

Wasaga Beach ON
Stay at this ski holiday home in Wasaga Beach. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Wasaga Beach Provincial Park and Wasaga ...
Opens in a new windowVILLA UPPER & LOWER SPECIAL RATES SLEEPS 15, VERY CLOSE TO BEACH ACCESS,
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Little Lake Escape | Waterfront 2 Bedroom Getaway

Little Lake Escape | Waterfront 2 Bedroom Getaway

Midland ON
Stay at this holiday home in Midland. Enjoy a garden, balconies and an in-room coffee maker. Popular attractions Little Lake Park and Huronia Museum are located ...
Opens in a new windowLittle Lake Escape | Waterfront 2 Bedroom Getaway
Georgian Bay Cottage-
Hot Tub/Sauna/Trail/Run/Bike/Swim//Marina!

Georgian Bay Cottage- Hot Tub/Sauna/Trail/Run/Bike/Swim//Marina!

Waubaushene ON
Stay at this holiday home in Tay. Enjoy free Wi-Fi, a sauna and a garden. Popular attractions Tay Township Public Library - Waubaushene Branch and Waubaushene ...
Opens in a new windowGeorgian Bay Cottage- Hot Tub/Sauna/Trail/Run/Bike/Swim//Marina!
HOT TUB-Natural paradise, timber frame, sauna, close to Casino and ski hill.

HOT TUB-Natural paradise, timber frame, sauna, close to Casino and ski hill.

Coldwater ON
Stay at this holiday home in Severn. Enjoy free Wi-Fi, a sauna and a garden. Popular attractions Matchedash Bay Trail Trailhead and Little Gem Island are located ...
Opens in a new windowHOT TUB-Natural paradise, timber frame, sauna, close to Casino and ski hill.
Sun, Sand and S'mores-The Great Escape
STRTT-2026-071

Sun, Sand and S'mores-The Great Escape STRTT-2026-071

Penetanguishene ON
Stay at this holiday home in Tiny. Enjoy laundry facilities, patios and an in-room coffee maker. Popular attractions Wahnekewaning Beach and Cawaja Beach are ...
Opens in a new windowSun, Sand and S'mores-The Great Escape STRTT-2026-071
Gorgian Bay cottage for rent in Tiny

Gorgian Bay cottage for rent in Tiny

Tiny ON
Stay at this holiday home in Tiny. Enjoy patios, an in-room coffee maker and in-room fireplaces. Popular attractions Wahnekewaning Beach and Cawaja Beach are ...
Opens in a new windowGorgian Bay cottage for rent in Tiny
Spectacular Waterfront three Bedroom Home!

Spectacular Waterfront three Bedroom Home!

Port McNicoll ON
Stay at this family-friendly holiday home in Tay. Enjoy free Wi-Fi, breakfast (surcharge) and a garden. Popular attractions Martyrs' Shrine and Sainte-Marie ...
Opens in a new windowSpectacular Waterfront three Bedroom Home!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Penetanguishene Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Penetanguishene vacation homes are the perfect way for you to wing it.

Holiday houses in Penetanguishene let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Penetanguishene in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Penetanguishene adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Penetanguishene with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Penetanguishene vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Penetanguishene Holiday Homes essential information

Accommodation
118 Holiday Homes
Lowest Price
NZ$143
Highest Price
NZ$879
Popular accommodation
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage, A-Frame Escape in the Woods of Georgian Bay, Muskoka, VILLA UPPER & LOWER SPECIAL RATES SLEEPS 15, VERY CLOSE TO BEACH ACCESS,, Little Lake Escape | Waterfront 2 Bedroom Getaway, Georgian Bay Cottage- Hot Tub/Sauna/Trail/Run/Bike/Swim//Marina!, HOT TUB-Natural paradise, timber frame, sauna, close to Casino and ski hill., Sun, Sand and S'mores-The Great Escape STRTT-2026-071, Gorgian Bay cottage for rent in Tiny, Spectacular Waterfront three Bedroom Home!

Top trending hotels in Penetanguishene

Quality Inn & Conference Centre

Quality Inn & Conference Centre

2.5 out of 5
924 King Street Midland ON
Fully refundable
The price is NZ$143 per night from 18 May to 19 May
NZ$143
18 May - 19 May
includes taxes & fees
Stay at this business-friendly hotel in Midland. Enjoy free breakfast, free parking and a fitness centre. Our guests praise the breakfast and the pool in their ...
Opens in a new windowQuality Inn & Conference Centre
Super 8 by Wyndham Midland

Super 8 by Wyndham Midland

2 out of 5
1144 Hugel Avenue Midland ON
Fully refundableReserve now, pay when you stay
The price is NZ$156 per night from 10 May to 11 May
NZ$156
10 May - 11 May
includes taxes & fees
Stay at this business-friendly motel in Midland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
Opens in a new windowSuper 8 by Wyndham Midland
Midland Inn & Suites

Midland Inn & Suites

2.5 out of 5
720 Prospect Blvd Midland ON
Fully refundableReserve now, pay when you stay
The price is NZ$149 per night from 10 May to 11 May
NZ$149
10 May - 11 May
includes taxes & fees
Stay at this hotel in Midland. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in their reviews. ...
Opens in a new windowMidland Inn & Suites
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Hampton Inn Midland, On

Hampton Inn Midland, On

2.5 out of 5
877 King Street Midland ON
Fully refundableReserve now, pay when you stay
The price is NZ$211 per night from 17 May to 18 May
NZ$211
17 May - 18 May
includes taxes & fees
Stay at this hotel in Midland. Enjoy free breakfast, free parking and a 24-hour fitness centre. Our guests praise the breakfast and the helpful staff in their ...
Opens in a new windowHampton Inn Midland, On
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.