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Holiday houses in Midland

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Top-rated holiday rentals in Midland

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

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Guest favourite
Guest suite in Moonstone
4.86 out of 5 average rating, 311 reviews

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.

Guest favourite
A spacious outdoor balcony features a wooden deck with a green and white patterned rug. Two chairs are positioned around a glass-top table, surrounded by lush greenery from neighboring trees. A large window on the wall offers natural light to the space.
Apartment in Midland
4.9 out of 5 average rating, 130 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.

Top Guest favourite
Cottage in Victoria Harbour
4.83 out of 5 average rating, 232 reviews

Serenity, Simplicity and Stone

This is a tiny cottage in a sleepy little hollow that opens onto the Georgian Bay. Inside, each stone was carefully chosen and the woodwork was built, piece by piece, by two craftsmen who are highly skilled and passionate about repurposing. It's an art that will leave you in awe; especially if you're worried about climate crisis. The coat hangers are upcycled 100-year-old railway spikes! If you're looking for luxury you will be disappointed but if you're a minimalist you're going to love it.

Top Guest favourite
A rustic wooden dining table is set with plates and jars of milk, complementing a cozy gas stove. Large windows frame views of the bay and surrounding nature, while soft curtains allow natural light to fill the room.
Tiny home in Waubaushene
5 out of 5 average rating, 240 reviews

Saltbox by the Bay + Snowshoes/Ski/Snowboard/Vetta

JANUARY AVAILS + Snowshoes + Skiing Welcome to Saltbox by the Bay, your 4-season escape. Perfect for couples, a small family/friends getaway or solo retreat. This vintage cottage is upcycled with luxe amenities. Made for slow living, play boardgames & classic albums & watch sunsets over the bay. Explore winter in cottage country: borrow our snowshoes for a trek, visit Quayle's Brewery, pamper yourself at Vetta Nordic Spa, ski/snowboard Mount St. Louis or head into town for dinner & bowling.

Top Guest favourite
A charming two-story house is captured against a clear blue sky. The exterior features horizontal grey siding, wooden accents, and a balcony above the entrance. A stone facade frames the lower part of the structure, while a garage door adds to the home's appeal.
Apartment in Penetanguishene
4.99 out of 5 average rating, 102 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 .

Guest favourite
Home in Victoria Harbour
4.84 out of 5 average rating, 151 reviews

Georgian Bay Paradise

Enjoy a relaxing vacation away from the hustle & bustle in this delightful 3 bedroom waterfront cottage. Just 90 minutes north of Toronto, this newly-renovated, gorgeous retreat is right on Georgian Bay, one of the world's most sought after destinations. Revel in breathtaking views, amazing sunsets and the privacy of numerous cedars. You will love the sun, sand, rock and waves which will captivate you. Access your own deck, lawn, and beach as well as many fun winter activities.

Top Guest favourite
Two wooden Adirondack chairs are positioned on a lush green lawn facing the water, framed by overhanging tree branches. The sunset creates a colorful display on the horizon, reflecting on the calm surface of the lake, while a small table holds a wine bottle and glasses.
Guesthouse in Victoria Harbour
4.96 out of 5 average rating, 284 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

Top Guest favourite
A modern garage apartment is displayed, featuring a neutral-toned exterior with a large garage door and a side entrance. A spacious driveway is visible, providing ample parking space. The entrance is highlighted by a white door, and trees are partially visible in the background.
Apartment in Midland
4.94 out of 5 average rating, 179 reviews

Hosted by 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.

Guest favourite
A cozy outdoor fire pit area is designed with smooth stones surrounding a crackling fire. Two black wooden chairs provide seating nearby. In the background, a cottage features string lights and large windows, nestled among trees in a serene garden setting.
Cottage in Tiny
4.93 out of 5 average rating, 333 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. Licence STRTT-2026-057

Guest favourite
Loft in Midland
4.89 out of 5 average rating, 396 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. Listing not suitable for ages under 6.

Top Guest favourite
A welcoming living area features a spacious sofa draped with soft blankets. A modern kitchen with white cabinetry and stainless steel appliances is visible. A cozy fireplace adds warmth, while large windows provide natural light, leading to a door opening to an outdoor space.
Apartment in Coldwater
4.97 out of 5 average rating, 126 reviews

Cozy getaway for two with hot tub!

Unwind in our peaceful guest suite attached to our home located near Mount St-Louis Moonstone, Vetta Nordic Spa and the cozy town of Coldwater. With its private entrance, hot tub (accessible daily between 8am and 10pm) and serene forest surroundings, this space is designed for guests who value calm, quiet and nature. We ask that guests share our appreciation for a tranquil environment.

Guest favourite
A hot tub is positioned on a wooden deck, illuminated with soft blue lights. Surrounding greenery adds a natural backdrop. The tranquil water surface reflects the gentle glow, creating a relaxing ambiance in the evening setting.
Cottage in Midland
4.87 out of 5 average rating, 247 reviews

House on the Hill, HotTub, Relaxation, Bike 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, running or biking, and discover a variety of local attractions just minutes away.

Popular amenities for Midland holiday rentals

When is the best time to visit Midland?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Midland?

    Midland has more than 110 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 Midland?

    Experience the best of Midland 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.

  • Are there pet-friendly vacation rentals in Midland?

    Four-legged friends are welcome in Midland. Choose from more than 70 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 100 vacation rentals in Midland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Midland vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 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 280 vacation rentals in Midland, and over 60 vacation rentals in Port McNicoll.

  • Do private suite rentals in Midland have air conditioning?

    Absolutely! We offer over 10 private suite rentals with air conditioning in Midland. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Midland have a kitchen?

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

  • Do private suite rentals in Midland have wifi?

    Absolutely! We offer over 10 private suite rentals with wifi in Midland. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Midland have free parking?

    Absolutely! We offer over 20 apartment rentals with free parking in Midland. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Midland

  • Total holiday rentals

    Explore 180 holiday rentals in Midland

  • Nightly prices starting at

    Midland holiday rentals start at $28 AUD per night before taxes and fees

  • Verified guest reviews

    Over 8,440 verified reviews to help you choose

  • Family-friendly holiday rentals

    110 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 70 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    100 properties have a dedicated workspace

  • Wi-Fi availability

    180 of Midland holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Midland rentals

  • 4.8 Average rating

    Midland stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore

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  5. Midland