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

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.

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.

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.

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.

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.

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.

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.

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.

Side Tracked in Muskoka
Welcome to Side Tracked in Muskoka, Muskoka’s premier railway-themed stay. Step back in time inside a beautifully restored Ontario Northland Railway Caboose No. 122. Thoughtfully designed, the interior pays homage to the caboose’s railway history while complementing Muskoka’s cozy cottage feel.
Popular amenities for Midland holiday rentals
Other great holiday rentals in Midland

Welcoming Waterfront Cottage

Cozy Downtown Private Retreat

Cozy Cottage with Private Beach Access

Georgian Bay Waterfront Cottage with Sandy Beach

Tiny Home Farm Stay

Guest suite near the lake

Steps From the Beach and Hiking Trails!

Georgian Bay Waterfront Cottage HotTub King Bed
When is the best time to visit Midland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $156 SGD | $161 SGD | $139 SGD | $158 SGD | $160 SGD | $171 SGD | $185 SGD | $189 SGD | $184 SGD | $158 SGD | $157 SGD | $160 SGD |
| 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 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 $51 SGD 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!
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- Blue Mountain Village
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- Beaver Valley Ski Club
- Osler Bluff Ski Club
- Devil's Glen Country Club
- Georgian Bay Islands National Park
- Three Mile Lake
- Torrance Barrens Dark Sky Conservation Area
- Scandinave Spa Blue Mountain
- Taboo Muskoka Resort & Golf
- Burl's Creek Event Grounds
- Kee To Bala
- Casino Rama Resort
- Menominee Lake
- Awenda Provincial Park
- Wasaga Beach Area
- Wye Marsh Wildlife Centre
- Sunset Point Park
- Mono Cliffs Provincial Park
- Bass Lake Provincial Park
- Centennial Beach
- Innisfil Beach Park
- Couchiching Beach Park





