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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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Top Guest favourite
Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.
Dome in Bradford West Gwillimbury
4.96 out of 5 average rating, 466 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...

Guest favourite
The master bedroom features a spacious bed with a decorative 'RELAX' pillow. Natural light fills the room through a window adorned with dark curtains. Wall art depicting serene landscapes complements the calming neutral tones, while a stylish lamp and small seating area add functional decor.
Loft in Midland
4.89 out of 5 average rating, 399 reviews

Nest By The Bay - Downtown Midland / Private Loft

Ideally located in downtown Midland, Nest By The Bay blends comfort and style, with everything you need just steps away. Park your car and enjoy a walkable GBay Getaway with shops, restaurants, and the waterfront close by. Midland Harbour is a short stroll from your door. Experience festivals, theatre, artisan shops, and a growing culinary scene year-round. Travelling with others? Ask about our second suite, “Perch By The Bay.” A two-night stay is preferred. We look forward to hosting your stay.

Top Guest favourite
The historic Beck House, a striking Victorian structure, stands with a distinctive red façade and slate roof. A spacious porch with white railings invites guests, while the well-kept lawn adds to its charm. A wooden sign identifies the property, blending history with a warm welcome.
Apartment in Penetanguishene
4.9 out of 5 average rating, 534 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.

Top Guest favourite
A vibrant garden showcases a variety of colorful flowers, with a prominent rock identified by the number 14. Lush greenery surrounds the area, adding to the inviting outdoor space in front of a brick house. Well-maintained lawns complement the floral displays.
Home in Penetanguishene
4.97 out of 5 average rating, 170 reviews

White Rolling Sands of Penetang by Theatre

Shores of Georgian Bay - enjoy a firepit in the backyard of a deep lot backing onto woods with trails. Local walking and cycling routes, vege and flower gardens from private sunny 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 (Midland) nearby.

Top Guest favourite
A modern kitchen features natural wood cabinetry and a large marble countertop island with seating. Stainless steel appliances, including an electric stove and refrigerator, are visible. The space is well-lit with recessed lighting, and decorative plants add a touch of warmth.
Apartment in Midland
4.91 out of 5 average rating, 142 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.

Guest favourite
A spacious glamping dome is nestled among lush green trees, showcasing large windows and a triangular design. The entrance is framed by rustic outdoor seating, and soft lighting emanates from inside, creating an inviting atmosphere amidst the surrounding foliage.
Dome in Utopia
4.95 out of 5 average rating, 267 reviews

Off-grid Glamping Dome Nestled in the Woods

Welcome to our private campsite in Utopia, ON. Our family’s glamping dome is your chance to experience a unique getaway surrounded by the sights & sounds of nature. Amenities include camping essentials & some glamping perks: king size bed, bbq, fireplace, Indoor incineration toilet, soap & water, outdoor shower (summer only), kettle, cooking utensils. Nearby is Purple Hill Lavender Farms, Drysdale's Tree Farm, Tiffin Conservation Area, Nottawasaga & golf courses. Wasaga Beach is 30 min away.

Top Guest favourite
The open-concept living area features a comfortable sofa set against wooden accents and a rustic coffee table. The kitchen is visible in the background, equipped with modern appliances. Large windows allow natural light to fill the space, complementing the warm tones of the wood flooring.
Guesthouse in Barrie
5 out of 5 average rating, 263 reviews

Warnica Coach House

Welcome to the Warnica Coach House! This unique and historic property will not disappoint! Built by George R. Warnica in 1900, this spectacular property was the recipient of the Heritage Barrie award in 2018. The Coach House where you will stay, once housed horses and carriages, has been completely renovated top to bottom in 2023 with the finest touches. We are centrally located with a 30 second drive from the 400, and an 8 minute walk to the waterfront, restaurants, and downtown fun.

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, 289 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, 193 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.

Top Guest favourite
A wooden deck surrounds a cozy cabin, featuring a shaded barbecue area and two hot tubs. Colorful flower pots add vibrancy, while a large red umbrella provides shade. Lush greenery surrounds the space, enhancing the outdoor setting.
Cottage in Tiny
4.96 out of 5 average rating, 297 reviews

Private 40 Acre Cottage with Hot Tub

Our two bedroom cabin + cubby (available in summers) by a scenic pond is a private getaway while close to the main road and many amenities. Private outdoor space includes hot tub, deck, fire pit, and walking trails. We have a barn with ping pong and foosball tables. We are 20 min to Barrie, 10 min to Midland, 20 min to Balm beach, Wasaga beach, Mt. St Louis and Horseshoe Valley resort.

Guest favourite
A dining area features a round table surrounded by six white chairs, complemented by a decorative plant. A glass-front cabinet displays glassware. A cozy seating area with a brown couch is visible in the background, accented by a light-colored wall and framed artwork.
Cottage in Midland
4.87 out of 5 average rating, 250 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.

Guest favourite
Tiny home in Waubaushene
4.95 out of 5 average rating, 468 reviews

Unique TinyHome

This is a unique space with great attention placed on details. I design and build unique livable spaces catered to the individual needs of my clients. I invite you to come experience high quality living in a modern tiny home and experience sustainable, affordable living in just 286 square ft.

Popular amenities for Midland holiday rentals

When is the best time to visit Midland?

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Avg. price$170 AUD$175 AUD$152 AUD$172 AUD$174 AUD$186 AUD$201 AUD$205 AUD$200 AUD$172 AUD$171 AUD$174 AUD
Avg. temp-7°C-6°C-1°C6°C12°C17°C20°C19°C15°C9°C3°C-3°C

Frequently Asked Questions

  • Are there family-friendly house rentals in Midland?

    Midland has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Midland with our house rentals, starting at about $60 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 house rentals in Midland?

    Four-legged friends are welcome in Midland. Choose from more than 20 house rentals for guests traveling with pets.

  • Are there house rentals with a dedicated workspace in Midland?

    Yes! Work meets play with ease at over 30 house 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 270 vacation rentals in Midland, and over 50 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 apartment rentals in Midland have wifi?

    Absolutely! We offer over 20 apartment 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 160 holiday rentals in Midland

  • Nightly prices starting at

    Midland holiday rentals start at $55 AUD per night before taxes and fees

  • Verified guest reviews

    Over 8,260 verified reviews to help you choose

  • Family-friendly holiday rentals

    110 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 60 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    160 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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