
Holiday houses in Midland
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Top-rated holiday rentals in Midland
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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.

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.

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.

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.

Saltbox by the Bay | Snowshoes/Ski/Snowboard/Vetta
DECEMBER 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.

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.

Secluded Lakeside Retreat - Atkins Hideaway
Tucked in the heart of Muskoka, this handcrafted timber frame cabin rests alongside a scenic spring-fed lake, surrounded by 8 acres of private forest. Only 10 minutes from Bracebridge, enjoy serene lake life and natural beauty while remaining close to town amenities, local shops, and eateries. Enjoy private dock relaxation, cozy cabin comforts, and outdoor fires. A Provincial Park Day Pass is included (*security deposit required) for added adventure. Come relax, recharge and reconnect.

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

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.

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-2025-008

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.

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
Other great holiday rentals in Midland

Welcoming Waterfront Cottage

New home|LAKE FRONT|Hot tub|20ft ceilings

Bunkie in the Pines

Spacious Apartment Facing The Severn River

Cozy Comfort by the Bay w/Jacuzzi

Steps From the Beach and Hiking Trails!

Boho Hideaway w/ Hot Tub, Sauna & Games

The Carriage Unit: 2 connecting rooms, 1 bathroom
When is the best time to visit Midland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $166 AUD | $163 AUD | $163 AUD | $190 AUD | $192 AUD | $205 AUD | $222 AUD | $227 AUD | $221 AUD | $187 AUD | $180 AUD | $181 AUD |
| Avg. temp | -7°C | -6°C | -1°C | 6°C | 12°C | 17°C | 20°C | 19°C | 15°C | 9°C | 3°C | -3°C |
Frequently Asked Questions
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 290 vacation rentals in Midland, and over 60 vacation rentals in Port McNicoll.
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.
How much does it cost to stay in cottage rentals in Midland?
Experience the best of Midland with our cottage 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.
Are there family-friendly apartment rentals in Midland?
Midland has more than 10 family-friendly apartment 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 50 house rentals with air conditioning in Midland. Enjoy a tailored experience with all the comforts you desire.
Are there apartment rentals with a dedicated workspace in Midland?
Yes! Work meets play with ease at over 10 apartment rentals in Midland featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for Cottage Rentals in Midland?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 30 homes with wifi, over 30 homes with air conditioning, over 40 homes with a kitchen, over 40 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Midland have free parking?
Absolutely! We offer over 60 house rentals with free parking 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.
Quick stats about holiday rentals in Midland

Total holiday rentals
Explore 190 holiday rentals in Midland

Nightly prices starting at
Midland holiday rentals start at $30 AUD per night before taxes and fees

Verified guest reviews
Over 8,770 verified reviews to help you choose

Family-friendly holiday rentals
120 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
110 properties have a dedicated workspace

Wi-Fi availability
180 of Midland holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Midland rentals

4.8 Average rating
Midland stays are highly rated by guests—averaging 4.8 out of 5!
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- Blue Mountain Village
- Snow Valley Ski Resort
- Beaver Valley Ski Club
- Devil's Glen Country Club
- Osler Bluff Ski Club
- Craigleith Ski Club
- Mount St. Louis Moonstone
- Rocky Crest Golf Club
- Port Carling Golf & Country Club
- Windermere Golf & Country Club
- The Georgian Peaks Club
- The Club At Bond Head
- Muskoka Lakes Golf and Country Club
- Muskoka Bay Resort
- Lake Joseph Golf Club
- The Georgian Bay Club
- Georgian Bay Islands National Park
- Barrie Country Club
- Alpine Ski Club
- Toronto Ski Club
- Mansfield Ski Club
- Hawk Ridge Golf & Country Club
- Springwater Golf Course
- Heritage Hills Golf Club




