Vacation rentals in Penetanguishene

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Top-rated vacation rentals in Penetanguishene

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Guest favorite

Loft in Midland

4.92 out of 5 average rating, 243 reviews

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

Jan 2 – 9

G$31,840 GYD per night

Guest favorite

Apartment in Penetanguishene

4.88 out of 5 average rating, 377 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.

Jan 21 – 28

G$26,471 GYD per night

Guest favorite

Apartment in Penetanguishene

4.92 out of 5 average rating, 120 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.

Aug 7 – 14

G$14,676 GYD per night

Guest favorite

Apartment in Midland

4.95 out of 5 average rating, 22 reviews

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.

Nov 5 – 12

G$14,180 GYD per night

Guest favorite

Home in Penetanguishene

4.97 out of 5 average rating, 143 reviews

White Rolling Sands of Penetanguishene by theatre

Enjoy a firepit in the private backyard of a large deep lot backing onto woods with trails. Local walking and cycling routes, or stay home and enjoy the veggie and flower gardens from 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 are nearby.

Apr 21 – 28

G$24,487 GYD per night

Guest favorite

Apartment in Penetanguishene

4.98 out of 5 average rating, 47 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 .

Dec 10 – 17

G$20,825 GYD per night

Guest favorite

Apartment in Penetanguishene

4.97 out of 5 average rating, 34 reviews

The Sunnyside Stay - 2BD in Midland on 15 acres

Welcome to The Sunnyside Stay! A bright and private guest suite is nestled within a hardwood forest on 15 acres! Walk, bike, or drive to beautiful downtown Midland for restaurants, bars, shopping, and beautiful waterfront parks and beaches on Georgian Bay & just a 1:30 minute drive from Toronto! There are many trails to explore on the property and direct access to mountain biking trails and the trans Canada paved trail. Enjoy the fire pit, and mingle with our small flock of friendly hens

Sep 20 – 27

G$31,755 GYD per night

Guest favorite

Cottage in Port McNicoll

4.98 out of 5 average rating, 123 reviews

Boe's Cottage: Newly Renovated - Great WIFI

Experience Southern Georgian Bay - Ontario's Four Season Playground. Just 90 Minutes from Toronto! Relax in our fully renovated 4 season cabin with all the amenities of home. Steps from the lake with parks, beaches, hiking, kayaking. And in the winter, snowshoe, skate, snowmobile, cross country & downhill skiing at Mount st. louis moonstone Great setup for a 'working' vacation with excellent WIFI 10 Minutes to Midland for restaurants & unique shopping experiences

Sep 21 – 28

G$23,509 GYD per night

Guest favorite

Guesthouse in Victoria Harbour

4.98 out of 5 average rating, 228 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

Oct 3 – 10

G$36,800 GYD per night

Guest favorite

Cottage in Torrance

4.97 out of 5 average rating, 193 reviews

Beautiful Nine Mile Lake

Beautiful Muskoka getaway! Newly renovated 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.

May 5 – 10

G$34,742 GYD per night

Guest favorite

Cottage in Tiny

4.94 out of 5 average rating, 203 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-2024-017

Dec 20 – 27

G$36,963 GYD per night

Superhost

Cottage in Port Severn

4.86 out of 5 average rating, 130 reviews

Cottage "Down By The Bay"

1 bdrm cottage in beautiful Port Severn, ON with firepit, WIFI, Heat and AC. Great location year round. Located on the main road into Honey Harbour, ON and close to amenities such as Tim Hortens, LCBO, gas stations and restaurants. Near water and beaches (NOT A WATERFRONT- Port Severn Park and Beach is 7 min drive) Right beside entrance to OFSC trails for snowmobiling Mount ST. Louis is a 20 min drive Fishing/ice fishing options nearby

Nov 19 – 26

G$17,213 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Penetanguishene vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Penetanguishene's top sights

Discovery Harbour119 locals recommend

The Boathouse Eatery109 locals recommend

World Famous Dock Lunch36 locals recommend

Phil's Family Restaurant15 locals recommend

Village Square Mall3 locals recommend

Flynn's Irish Pub30 locals recommend

Other great vacation rentals in Penetanguishene

Guest favorite

Cottage in Penetanguishene

5.0 out of 5 average rating, 13 reviews

Cottage Retreat: HotTub, PingPong, Pool, Fireplace

Jan 17 – 24

G$50,769 GYD per night

Guest favorite

Guest suite in Penetanguishene

4.96 out of 5 average rating, 52 reviews

Nature’s Garden Couple Retreat 21 Park St Penetang

Sep 20 – 27

G$14,319 GYD per night

Guest favorite

Guest suite in Port McNicoll

4.93 out of 5 average rating, 29 reviews

Private farmhouse studio (full bath/kitchen)

Jul 29 – Aug 5

G$20,687 GYD per night

Guest favorite

Cabin in Penetanguishene

4.83 out of 5 average rating, 18 reviews

Pet Friendly Nostalgic Cabin

Sep 11 – 18

G$26,802 GYD per night

Guest favorite

Cottage in Penetanguishene

4.95 out of 5 average rating, 22 reviews

Georgian Bay Escape

Mar 12 – 19

G$28,704 GYD per night

Guest favorite

Apartment in Midland

4.91 out of 5 average rating, 58 reviews

Chez Nous Midland

Dec 24 – 31

G$17,516 GYD per night

Guest favorite

Apartment in Midland

4.99 out of 5 average rating, 72 reviews

Inn At Little Lake

Sep 13 – 20

G$16,405 GYD per night

Guest favorite

Home in Midland

5.0 out of 5 average rating, 42 reviews

Historic Coach House hosted by John & Donna

Jul 2 – 9

G$25,976 GYD per night

Show all

Quick stats about vacation rentals in Penetanguishene

Total rentals
90 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
2.7K reviews
Nightly prices starting at
G$4,180 GYD before taxes and fees

Frequently Asked Questions

Do cottage rentals in Penetanguishene have a kitchen?
Absolutely! We offer over 20 cottage 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 house rentals in Penetanguishene have free parking?
Absolutely! We offer over 20 house rentals with free parking in Penetanguishene. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Penetanguishene have air conditioning?
Absolutely! We offer over 20 house 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 Apartment Rentals in Penetanguishene?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with free parking, over 10 homes with air conditioning, over 10 homes with a kitchen, 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 apartment rentals in Penetanguishene?
Experience the best of Penetanguishene with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Vacation rentals in Penetanguishene

Top-rated vacation rentals in Penetanguishene

Vacation rentals for every style

Cottages

Houses

Hotels

Popular amenities for Penetanguishene vacation rentals

Stay near Penetanguishene's top sights

Other great vacation rentals in Penetanguishene

Cottage in Penetanguishene

Guest suite in Penetanguishene

Guest suite in Port McNicoll

Cabin in Penetanguishene

Cottage in Penetanguishene

Apartment in Midland

Apartment in Midland

Home in Midland

Quick stats about vacation rentals in Penetanguishene

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do cottage rentals in Penetanguishene have a kitchen?

Are there vacation rentals with a dedicated workspace in Penetanguishene?

Do house rentals in Penetanguishene have free parking?

Do house rentals in Penetanguishene have air conditioning?

Are there pet-friendly vacation rentals in Penetanguishene?

Are there Penetanguishene vacation rentals on Airbnb with pools?

Do house rentals in Penetanguishene have wifi?

What are the most popular amenities for Apartment Rentals in Penetanguishene?

Are there family-friendly vacation rentals in Penetanguishene?

How much does it cost to stay in apartment rentals in Penetanguishene?

Destinations to explore