Vacation rentals in Midland

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Top-rated vacation rentals in Midland

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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

Place to stay in Wasaga Beach

5.0 out of 5 average rating, 190 reviews

Newly Built Woodsy Loft Retreat

Welcome to Woodsy Loft, a newly built retreat. A great spot for a getaway! A perfect home base for not just the beach and stunning walks into the sunset, but Blue Mtn, Scandinavian Spa, Collingwood, Cross Country Skiing Provincial Park and a brand new casino, all close by. Packed with amenities like screened in patio, XL bathtub, King size bed, 'The Frame' Smart TV, full kitchen, fast WIFI, motorized blind...and the list goes on. Situated and designed to offer max. privacy and relaxation.

Sep 16 – 23

G$29,464 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

Loft in Midland

4.88 out of 5 average rating, 285 reviews

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. 2 nights min. preferred, 1 night by request. Listing not suitable for ages under 6.

Dec 31 – Jan 7

G$28,519 GYD per night

Guest favorite

Farm stay in Gravenhurst

4.98 out of 5 average rating, 369 reviews

Stix N Stones (Includes Light Breakfast & Kayaks)

Nestled in the woods on Walkers Point, this is a great opportunity to reconnect with nature. We promise when you leave you’ll appreciate the forest as much as the water that surrounds us. Although we are not on the water, we are a 3min drive to a semi-private beach. Kayaks & life vests included (& delivered). Snowshoes incl in winter. Light breakfast is yogurt & fruit. Short distance to renowned hiking trails, Hardy Lake Park, Sawdust City & Clearlake Brewery, Muskoka Winery.

Dec 28 – Jan 4

G$24,930 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 Midland vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Midland's top sights

Wye Marsh Wildlife Centre156 locals recommend

Martyrs' Shrine80 locals recommend

Discovery Harbour119 locals recommend

McDonald's6 locals recommend

The Boathouse Eatery109 locals recommend

Mom's Restaurant19 locals recommend

Other great vacation rentals in Midland

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

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

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

Guest favorite

Apartment in Midland

4.98 out of 5 average rating, 62 reviews

Cozy Downtown Private Retreat

Nov 5 – 12

G$30,305 GYD per night

Guest favorite

Apartment in Penetanguishene

4.98 out of 5 average rating, 47 reviews

By The Bay spacious one bedroom

Dec 10 – 17

G$20,825 GYD per night

Guest favorite

Townhouse in Midland

5.0 out of 5 average rating, 16 reviews

Gorgeous 3BR Home in Midland's Premier Location

May 15 – 22

G$27,765 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

Sep 20 – 27

G$31,755 GYD per night

Show all

Quick stats about vacation rentals in Midland

Total rentals
230 properties
Rentals with a pool
20 properties have a pool
Pet-friendly rentals
90 properties allow pets
Family-friendly rentals
150 properties are a good fit for families
Total number of reviews
7K reviews
Nightly prices starting at
G$4,180 GYD before taxes and fees

Frequently Asked Questions

Are there pet-friendly vacation rentals in Midland?
Four-legged friends are welcome in Midland. Choose from more than 90 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Midland?
Yes! Work meets play with ease at over 140 vacation rentals in Midland featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for Apartment Rentals in Midland?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 30 homes with free parking, over 30 homes with a kitchen, over 30 homes with wifi, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
How much does it cost to stay in cottage rentals in Midland?
Experience the best of Midland with our cottage rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Midland have wifi?
Absolutely! We offer over 50 cottage rentals with wifi in Midland. Enjoy a tailored experience with all the comforts you desire.
Are there Midland vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Midland, available on Airbnb. Make a splash and soak up the sun in style!
Where should I stay in Midland?
Make yourself at home in Midland by choosing from our most frequently booked neighborhoods. We have over 90 vacation rentals in Port McNicoll, and over 300 vacation rentals in Penetanguishene.
Do cottage rentals in Midland have a kitchen?
Absolutely! We offer over 50 cottage rentals with a kitchen in Midland. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Midland?
Midland has more than 150 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Midland have air conditioning?
Absolutely! We offer over 70 house rentals with air conditioning in Midland. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Midland

Top-rated vacation rentals in Midland

Vacation rentals for every style

Houses

Cottages

Apartments

Popular amenities for Midland vacation rentals

Stay near Midland's top sights

Other great vacation rentals in Midland

Apartment in Midland

Guest suite in Port McNicoll

Apartment in Midland

Home in Midland

Apartment in Midland

Apartment in Penetanguishene

Townhouse in Midland

Apartment in Penetanguishene

Quick stats about vacation rentals in Midland

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there pet-friendly vacation rentals in Midland?

Are there vacation rentals with a dedicated workspace in Midland?

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

How much does it cost to stay in cottage rentals in Midland?

Do cottage rentals in Midland have wifi?

Are there Midland vacation rentals on Airbnb with pools?

Where should I stay in Midland?

Do cottage rentals in Midland have a kitchen?

Are there family-friendly vacation rentals in Midland?

Do house rentals in Midland have air conditioning?

Destinations to explore