Vacation rentals in Midland

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Midland

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 201 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Feb 21 – 28

$106 per night
Superhost

Guest suite in Moonstone

4.82 out of 5 average rating, 156 reviews

SKI, Trails 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.

May 10 – 17

$92 per night
Guest favorite

Apartment in Penetanguishene

4.88 out of 5 average rating, 374 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.

May 26 – Jun 2

$113 per night

Popular amenities for Midland vacation rentals

Stay near Midland's top sights

Discovery Harbour119 locals recommend
Martyrs' Shrine80 locals recommend
McDonald's6 locals recommend
The Boathouse Eatery109 locals recommend
Mom's Restaurant19 locals recommend
Real Canadian Superstore44 locals recommend

Other great vacation rentals in Midland

Guest favorite

Cottage in Torrance

4.97 out of 5 average rating, 190 reviews

Beautiful Nine Mile Lake

Apr 23 – 30

$153 per night
Guest favorite

Home in Penetanguishene

4.97 out of 5 average rating, 134 reviews

Tiny House in Penetanguishene

Jul 11 – 18

$180 per night
Guest favorite

Home in Port McNicoll

4.94 out of 5 average rating, 183 reviews

Spectacular Waterfront 3 Bedroom Home!

Apr 26 – May 3

$249 per night
Guest favorite

Place to stay in Wasaga Beach

5.0 out of 5 average rating, 186 reviews

Newly Built Woodsy Loft Retreat

Nov 16 – 23

$128 per night
Guest favorite

Apartment in Midland

4.91 out of 5 average rating, 58 reviews

Chez Nous Midland

Aug 19 – 26

$74 per night
Guest favorite

Apartment in Midland

4.99 out of 5 average rating, 70 reviews

Inn At Little Lake

Apr 15 – 22

$66 per night
Guest favorite

Apartment in Midland

4.94 out of 5 average rating, 18 reviews

Loft By The Bay

Aug 20 – 27

$100 per night
Guest favorite

Home in Midland

5.0 out of 5 average rating, 42 reviews

Historic Coach House hosted by John & Donna

Aug 7 – 14

$111 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

May 27 – Jun 3

$107 per night
Guest favorite

Vacation home in Midland

4.85 out of 5 average rating, 27 reviews

Cheerful 3 bedroom fully equipped vacation home

Apr 24 – May 1

$103 per night
Guest favorite

Apartment in Penetanguishene

4.98 out of 5 average rating, 47 reviews

By The Bay spacious one bedroom

Feb 23 – Mar 2

$88 per night
Guest favorite

Loft in Midland

4.95 out of 5 average rating, 65 reviews

Loft on King- Downtown Midland

Aug 22 – 29

$162 per night

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

6.8K reviews

Nightly prices starting at

$20 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 130 vacation rentals in Midland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • What are the most popular amenities for Guesthouse Rentals in Midland?

    Enhance your stay in our Guesthouse Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • How much does it cost to stay in cabin rentals in Midland?

    Experience the best of Midland with our cabin 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.

  • Do apartment rentals in Midland have wifi?

    Absolutely! We offer over 30 apartment 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 300 vacation rentals in Penetanguishene, and over 90 vacation rentals in Port McNicoll.

  • Do apartment rentals in Midland have a kitchen?

    Absolutely! We offer over 30 apartment 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 apartment rentals in Midland have air conditioning?

    Absolutely! We offer over 30 apartment rentals with air conditioning in Midland. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Simcoe County
  5. Midland