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Holiday rentals in Midland

Find and book unique accommodation on Airbnb

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
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.
Flat in Penetanguishene
4.89 out of 5 average rating, 529 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.
Flat in Midland
4.91 out of 5 average rating, 137 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, 265 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
Tiny home in Waubaushene
5 out of 5 average rating, 248 reviews

Saltbox by the Bay | 4-Seasons | Bikes | Vetta Spa

*GUEST BIKES AVAILABLE* Welcome to Saltbox by the Bay, your 4-season escape. Perfect for couples, a small family/friends getaway or solo retreat. This vintage cottage has been reimagined with luxe amenities & cozy vibes. Play boardgames & classic albums, as you watch sunsets over the bay. Experience cottage country, year round. Walk or bike the Tay Shore Trail, visit Quayle's Brewery, pamper yourself at Vetta Nordic Spa, enjoy some glow-in-the dark bowling & explore charming nearby towns.

Guest favourite
A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.
Cottage in Tiny
4.96 out of 5 average rating, 151 reviews

Ultimate Georgian Bay Vacation Getaway

Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

Top guest favourite
Guest house in Barrie
5 out of 5 average rating, 257 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.

Guest favourite
A serene sunset is captured over Georgian Bay, with warm orange and gold hues reflecting on the water. Silhouetted figures are seated on a dock, gazing out towards the horizon, creating a sense of tranquil evening ambiance.
Home in Victoria Harbour
4.84 out of 5 average rating, 153 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
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, 364 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.

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.
Guest house in Victoria Harbour
4.96 out of 5 average rating, 287 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.
Flat in Midland
4.94 out of 5 average rating, 189 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 favourite
An outdoor fire pit surrounded by gravel is present, featuring two wooden chairs. A hot tub is located nearby, positioned in front of a geodesic dome with large windows. String lights are draped overhead, illuminating the outdoor space.
Dome in Utopia
4.96 out of 5 average rating, 170 reviews

Glamping Dome Riverview Utopia

Come retreat into nature at the Riverview Glamping Dome… a 4 season getaway located on Rustic Roots Farm and Eco-retreat 1 hour north of Toronto. Whether you're looking for a romantic getaway or to come disconnect from the hustle and bustle of everyday life this geodesic dome is for you! Located on 64 sprawling acres come explore hiking trails, go fishing, relax in the hot tub, and stargaze fireside.

Popular amenities for Midland holiday rentals

When is the best time to visit Midland?

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Avg. price£81£79£79£93£93£100£108£110£107£93£92£93
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 cottage rentals in Midland have air conditioning?

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

  • Do house rentals in Midland have a kitchen?

    Absolutely! We offer over 50 house 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 cottage rentals in Midland have free parking?

    Absolutely! We offer over 30 cottage 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 £30 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 & child-friendly amenities

  • Pet-friendly holiday rentals

    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

  • Wifi availability

    160 of Midland holiday rentals include wifi 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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  3. Ontario
  4. Simcoe County
  5. Midland