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Vacation rentals in Midland

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Top-rated vacation rentals in Midland

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

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Guest suite in Moonstone

4.83 out of 5 average rating, 194 reviews

SKI & 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.

Dome in Bradford West Gwillimbury

4.96 out of 5 average rating, 294 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...

Loft in Midland

4.93 out of 5 average rating, 283 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

Rental unit in Penetanguishene

4.92 out of 5 average rating, 159 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.

Rental unit in Penetanguishene

4.88 out of 5 average rating, 432 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.

Tiny home in Waubaushene

5 out of 5 average rating, 150 reviews

Saltbox by the Bay | Tiny House | 4-Season Cottage

Welcome to your 4-season, bayside escape. Relax & unwind to swaying reeds & water views in this vintage cottage, upcycled with luxe amenities. Make gourmet meals, listen to albums & play boardgames, as you watch sunsets over the bay. Known as the Heart of Georgian Bay, explore some of the best of cottage country: swim at a local beach, trek Wye Marsh, visit beautiful Quayle's Brewery, pamper yourself at Vetta Nordic Spa, bike ride the Tay Shore Trail or visit one of the quaint nearby towns.

Guesthouse in Victoria Harbour

4.96 out of 5 average rating, 256 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

Rental unit in Midland

4.95 out of 5 average rating, 100 reviews

Chez 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.

Cottage in Tiny

4.94 out of 5 average rating, 237 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

Guest suite in Midland

4.98 out of 5 average rating, 106 reviews

Inn At Little Lake

Our place is located on a quiet street that backs onto Little Lake. Access to Little Lake Park is close by where there is hiking trails, swimming, a restaurant, lawn bowling, rowing club, free tennis courts and a local disc golf course. We are a 15 minute walk to downtown with many great restaurants, shops, art gallery, theatre, library and the town docks. My place is good for couples, solo adventurers, and business travelers.

Home in Midland

4.84 out of 5 average rating, 195 reviews

The Little Lake House

The Little Lake House can be described as charming, and cozy. Located close to downtown, and a short walk from Little Lake Park, this newly renovated house is a sweet spot for your next stay in Midland. Relax, and read a book in the little backyard. Go out for a scrumptious meal downtown, or choose to stay in, and cook in our airy & bright kitchen. With 2 cozy bedrooms, you'll feel well rested in one of our pillow-top beds.

Cottage in Midland

4.87 out of 5 average rating, 183 reviews

House on the Hill, HotTub, Ski, Ice Fish, Trails

Experience the perfect blend of historic charm and modern comfort in this century home. Bask in the refreshing breeze from Georgian Bay and enjoy the tranquility it brings. Explore nearby downtown shops, take advantage of the Trans Canada Trail for walking or biking, and discover a variety of local attractions just minutes away.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Popular amenities for Midland vacation rentals

Free parking on premises

Air conditioning

Stay near Midland's top sights

Wye Marsh Wildlife Centre156 locals recommend

Discovery Harbour119 locals recommend

The Boathouse Eatery109 locals recommend

Martyrs' Shrine80 locals recommend

Dillon's Wood Fired Pizza57 locals recommend

King's Wharf Theatre56 locals recommend

Other great vacation rentals in Midland

Home in Georgian Bay

5 out of 5 average rating, 61 reviews

A-Frame in the Woods of GeorgianBay, Muskoka

Cabin in Innisfil

5 out of 5 average rating, 27 reviews

Brand New - A-frame w Hot Tub!

Cottage in Penetanguishene

4.95 out of 5 average rating, 38 reviews

Georgian Bay Escape

Rental unit in Penetanguishene

4.88 out of 5 average rating, 83 reviews

Quiet & Pristine Georgian Bay Escape near trails

Cabin in Tiny

5 out of 5 average rating, 6 reviews

The Beach House, Georgian Bay, Beach View w/ Sauna

Bungalow in Midland

4.93 out of 5 average rating, 28 reviews

Boho Hideaway Retreat w/ Hot Tub & Sauna!

Dome in Tay

4.97 out of 5 average rating, 33 reviews

The Secret Garden - Dome Escape

Cottage in Port McNicoll

4.92 out of 5 average rating, 38 reviews

Steps to beach - 1.5 hr from Toronto

Quick stats about vacation rentals in Midland

Total rentals
220 properties
Nightly prices starting at
$20 before taxes and fees
Total number of reviews
8.2K reviews
Family-friendly rentals
150 properties are a good fit for families
Pet-friendly rentals
80 properties allow pets
Rentals with a pool
30 properties have a pool

Frequently Asked Questions

Are there pet-friendly cottage rentals in Midland?
Four-legged friends are welcome in Midland. Choose from more than 20 cottage rentals for guests traveling with pets.
Are there house rentals with a dedicated workspace in Midland?
Yes! Work meets play with ease at over 50 house rentals in Midland featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in cabin rentals in Midland?
Experience the best of Midland with our cabin 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 house rentals in Midland have wifi?
Absolutely! We offer over 80 house rentals with wifi in Midland. Enjoy a tailored experience with all the comforts you desire.
Are there Midland house rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 house rentals 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 80 vacation rentals in Port McNicoll, and over 270 vacation rentals in Penetanguishene.
Do cottage rentals in Midland have a kitchen?
Absolutely! We offer over 40 cottage rentals with a kitchen in Midland. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly cottage rentals in Midland?
Midland has more than 40 family-friendly cottage rentals. 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.
Do private suite rentals in Midland have free parking?
Absolutely! We offer over 10 private suite rentals with free parking in Midland. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore