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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.

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Top guest favorite
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, 538 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 favorite
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, 174 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 favorite
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, 146 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 favorite
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, 270 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 favorite
A quaint blue cottage features a welcoming front deck with two yellow chairs facing the lush green lawn. The cottage is surrounded by trees and showcases large windows that bring natural light into the interior.
Tiny home in Waubaushene
5 out of 5 average rating, 253 reviews

Saltbox by the Bay | Views, Bikes, Beaches & Vetta

*SUMMER AVAILS* *GUEST BIKES* Welcome to Saltbox by the Bay, a cozy vintage cottage with beautiful views & luxe amenities. Perfect as a couples getaway, small family/friends vacation or solo retreat. Ease into slow living, cook your favourite meals, play boardgames & albums, as you watch birds & sunsets over the bay. Walk or borrow our bikes for the Tay Shore Trail, visit nearby beaches & Quayle's Brewery, pamper yourself at Vetta Nordic Spa & explore charming towns around Georgian Bay.

Top guest favorite
A cozy bedroom features a wooden headboard with a herringbone pattern and decorative elements. Two bedside tables hold lamps and small plants, while a wall display includes round mirrors and framed signs. Light-colored bedding is complemented by a decorative pillow, creating a welcoming ambiance.
Loft in Midland
4.92 out of 5 average rating, 372 reviews

Perch by the Bay - Downtown Midland / Private Loft

Welcome to Perch By The Bay, a stylish retreat in downtown Midland. Park for free and walk to Midland Harbour, shops, restaurants, cafe's and waterfront trail. Enjoy festivals, theatre, artisan markets, and great dining nearby. Local sights, include Vetta Nordic Spa, Multicultural Centre, Horseshoe, Moonstone, Saint Marie, King's Wharf & Discovery Harbour. Traveling with others? Our sister Airbnb, Nest By The Bay, is a 2 bedroom private loft at the rear of this building.

Guest favorite
The geodesic dome features a modern white exterior, set against a backdrop of trees. A wooden deck extends from the dome, leading to a covered gazebo, with a pathway of wood chips guiding the approach. Soft sunlight filters through the branches, creating a serene atmosphere.
Dome in Uxbridge
4.85 out of 5 average rating, 117 reviews

The Bubble Glamping Dome

Escape to a luxury geodesic dome on our scenic farm, nestled at the edge of the forest. Fully equipped with heating, cooling, a private washroom, deck, and hot tub, it’s the perfect blend of comfort and nature. Explore the farm, meet our sheep, chickens, and livestock guardian dog, or hike over 100 acres of connected regional forest. Whether you’re relaxing under the stars or adventuring outdoors, this unique glamping retreat promises an unforgettable experience.

Top guest favorite
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, 292 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

Guest favorite
A hot tub is set under wooden beams, providing a calming retreat. It overlooks a grassy area leading to the waterfront, where bright red Muskoka chairs are positioned. Steps lead up to the deck, enhancing outdoor accessibility and views.
Home in Victoria Harbour
4.88 out of 5 average rating, 104 reviews

Modern Waterfront Home on Georgian Bay w/ Hot Tub!

Escape to a peaceful haven with this new and breathtaking modern waterfront cottage. Immerse yourself in the stunning views from the walkout deck with outdoor seating, a hot tub and a BBQ area. Quiet neighbourhood in Victoria Harbour on Georgian Bay. Short drive to charming town of Midland and nearby attractions such as the Tay Shore Trail and the Wye Marsh Wildlife Centre. This bright and beautifully finished home is less than a 2-hour drive from the GTA.

Top guest favorite
A living area features a modern fireplace below a large flat-screen television, providing an inviting focal point. A comfortable chair and a small lamp create a cozy reading nook, while a wooden coffee table sits atop an area rug, enhancing the warm ambiance.
Apartment in Midland
4.94 out of 5 average rating, 196 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.

Top guest favorite
A white dome structure is surrounded by greenery, featuring a wooden deck and railing. A picnic table made of natural wood is positioned in the foreground, offering a place to relax outdoors. The landscape includes grass and shrubbery, contributing to a serene outdoor setting.
Dome in East Gwillimbury
4.94 out of 5 average rating, 163 reviews

Starry nights…

Do you like camping without the camping? If so, hang out here at the farm for a day or the weekend. Enjoy the stars, have a sauna (ice bath extra $75.00) outdoor shower and a campfire, see deer, or wild turkeys or listen to nothing for a while. Feed the donkeys and chickens or grab a Muskoka chair and a book. It is your time to relax and unwind !

Guest favorite
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, 254 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 vacation rentals

When is the best time to visit Midland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$25,731 GYDG$26,568 GYDG$23,011 GYDG$26,149 GYDG$26,358 GYDG$28,241 GYDG$30,542 GYDG$31,170 GYDG$30,333 GYDG$26,149 GYDG$25,940 GYDG$26,358 GYD
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 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 private suite rentals in Midland?

    Experience the best of Midland with our private suite 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 60 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 90 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 270 vacation rentals in Midland, and over 50 vacation rentals in Port McNicoll.

  • Do apartment rentals in Midland have air conditioning?

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

  • Do apartment rentals in Midland have a kitchen?

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

  • Do cottage rentals in Midland have wifi?

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

  • Do house rentals in Midland have free parking?

    Absolutely! We offer over 50 house rentals with free parking in Midland. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Midland

  • Total vacation rentals

    Explore 160 vacation rentals in Midland

  • Nightly prices starting at

    Midland vacation rentals start at G$8,368 GYD per night before taxes and fees

  • Verified guest reviews

    Over 8,260 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    90 properties have a dedicated workspace

  • Wi-Fi availability

    160 of Midland vacation 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

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