Holiday Rentals in Midland

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Midland holiday rentals
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198 Holiday rentals and Airbnb in Midland

Best family friendly Midland holiday rentals

Among the 198 accommodations in Midland, here are the 4 best family friendly rentals

The Wright House - Modern 3bdrm Home In Midland! - Midland
10 37 reviews

The Wright House - Modern 3bdrm Home In Midland!

apartment, Midland
This modern three-bedroom townhouse is situated in a quiet Midland neighbourhood, within walking distance of Georgian Bay General Hospital and local shops, and a short drive (approximately 8km) from Midland's town centre and attractions such as Marty's Shrine and St. Marie Among the Hurons.
The self-catering property sleeps six guests, offering a newly renovated open-plan living space with modern amenities including stainless steel appliances, a Keurig coffee maker, and a Samsung Smart TV; it also includes a garage for bike storage and a 10% discount on Georgian Spirit Cruises is available.
Eco Bay Chalet Year Round Group Stay In Muskoka - Midland
9.7 103 reviews

Eco Bay Chalet Year Round Group Stay In Muskoka

apartment, Severn
This luxurious five-bedroom, four-bathroom Severn chalet boasts 5800 sq ft of waterfront space overlooking Georgian Bay, minutes from a public dock and beach.
The property offers a chef's kitchen, jacuzzi, sauna, fitness centre, and parking, accommodating up to 16 guests and providing access to non-motorised watersports on a private bay.
Sunset Waterfront Cottage  Bbq  Dock  Kayaks - Midland
9.1 13 reviews

Sunset Waterfront Cottage Bbq Dock Kayaks

apartment, Midland
This apartment is located in a convenient district of Midland, offering easy access to local attractions, including the Midland Museum of Art, which is 2.5 kilometers away.
This dwelling offers accommodation for up to 8 guests with 3 bathrooms and high-speed internet, providing a comfortable base for exploring Midland's offerings.
Duke's Point - Georgian Bay Island Cottage - Midland
10 4 reviews

Duke's Point - Georgian Bay Island Cottage

apartment
This Brousseau Island cottage offers a unique island retreat situated on the southeast corner of Brousseau Island in south Georgian Bay, accessible by boat, between Port Severn and Honey Harbour.
This renovated 3-bedroom holiday home, approximately 56 square metres, accommodates up to six guests and features a screened-in porch with bay views, a granite shoreline ideal for wildlife spotting, and opportunities for swimming and paddling.

Best Midland holiday rentals with parking

Downtown Luxury Loft With Rooftop Terrace - Midland
10 15 reviews

Downtown Luxury Loft With Rooftop Terrace

apartment, Midland
This stylish loft apartment is located in downtown Midland, just a few steps from the waterfront, harbourfront trails, restaurants, and shops.
This 111.5 square meter loft sleeps four guests across two Queen beds and features a fully equipped kitchen, in-suite laundry, high-speed Wi-Fi, and a private rooftop terrace with Midland Bay views, a gazebo, sky bar, and BBQ.
Beautiful & Spacious All-season Waterfront Cottage - Midland
9.9 31 reviews

Beautiful & Spacious All-season Waterfront Cottage

apartment
This charming cottage is located just a short drive from the town of Penetanguishene, on the shores of Georgian Bay, offering stunning views and easy access to the area's attractions. It has received excellent ratings for location, cleanliness, and overall experience, making it a popular choice for travellers.
The cottage features four bedrooms and two bathrooms, comfortably accommodating up to eight guests. Enjoy a fully equipped kitchen, a relaxing living area with a fireplace, modern conveniences like Wi-Fi and a washer/dryer, and a private garden with parking.
The Wright House - Modern 3bdrm Home In Midland! - Midland
10 8 reviews

The Wright House - Modern 3bdrm Home In Midland!

apartment, Midland
This Midland holiday home enjoys a central location, a 15-minute walk from Little Lake Park and Georgian Bay General Hospital, and within 3.2km of Midland Golf and Country Club and Bamboo Spa.
The 139 square metre property offers three bedrooms, three bathrooms, sleeps six guests, and includes a fully equipped kitchen, private balcony, free Wi-Fi, and access to a spa.
Sandy Beach/boating/swimming/hot Tub/marina/trails - Midland
8.9 59 reviews

Sandy Beach/boating/swimming/hot Tub/marina/trails

cottage, Midland
This charming waterfront cottage in Midland is just a short walk from the beautiful shores of Lake Huron and Georgian Bay, and within easy reach of the historical Sainte-Marie among the Hurons and Martyrs' Shrine. The property has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
The cottage offers three bedrooms, comfortably accommodating up to 12 guests. Enjoy a range of features including a fully equipped kitchen, a cosy fireplace, a terrace, a garden, a tennis court, and a Jacuzzi, perfect for relaxing and enjoying the stunning views.

Frequently asked questions about holiday rentals in Midland

  • What are the top family-friendly attractions in Midland?

    Midland is a great place for families. The Huronia Museum is a popular choice, with interactive exhibits on the history of the region. You can also take a scenic boat tour on Georgian Bay, or spend a day at the beach at Little Lake Park. For a fun day out, head to the Midland Bay Landing, with its playground, splash pad, and scenic walking trails.
  • What are the best Airbnb and holiday rentals in Midland?

  • When is the best time to book a vacation rental in Midland?

    The best time to book a vacation rental in Midland is during the shoulder seasons, from April to May and September to October. You'll find fewer crowds and lower prices during these months, making it a great time to enjoy the town's attractions without the summer rush.
  • What are the most popular Airbnbs in Midland?

  • What events or festivals should visitors check out in and around Midland?

    The Midland Waterfront Festival is a popular event that takes place in July, featuring live music, food vendors, and family activities. The annual Midland Fall Fair, held in September, is another great option, with agricultural displays, live entertainment, and carnival rides. In the surrounding area, you can also check out the Collingwood Elvis Festival and the Barrie Ribfest.
  • What are the best holiday rentals with a pool in Midland?

  • What are the best budget-friendly activities in Midland?

    Midland has plenty of budget-friendly activities. You can explore the town's scenic walking trails, such as the waterfront trail along the Georgian Bay. The Midland Public Library offers free events and programs throughout the year. You can also enjoy a picnic at Little Lake Park or take a free guided tour of the Huronia Museum.
  • What are the best rentals for families and kids in Midland?

  • What are the best restaurants with local dishes in Midland?

    For local cuisine, you should try The Old Stone Restaurant, known for its fresh seafood and classic Canadian dishes. Another favourite is The Bayside Grill, offering a casual atmosphere and delicious burgers and fries. For a more upscale dining experience, head to The Georgian Bay Club, renowned for its fine dining and panoramic views of the bay.
  • What are the best rentals or Airbnbs with a jacuzzi in Midland?

  • What are the best walking or cycling routes in Midland?

    The Waterfront Trail is a popular choice for both walking and cycling, offering stunning views of Georgian Bay. For a longer ride, consider the scenic route to Penetanguishene, passing through charming villages and picturesque farmland. If you're looking for a more challenging route, the trail to the top of Mount St. Louis Moonstone offers breathtaking views of the surrounding area.
  • Are there pet-friendly attractions in Midland?

    Yes, Midland is very pet-friendly. Little Lake Park has a designated dog park, and many restaurants and shops welcome well-behaved dogs. You can also enjoy scenic walks with your furry friend along the waterfront trail or through the town's parks.
  • What are the benefits of choosing a vacation rental in Midland?

    Vacation rentals offer more space and privacy compared to hotels, often at a more affordable price. You can enjoy the comforts of home, such as a fully equipped kitchen and laundry facilities. Many rentals also have unique features and amenities that cater to specific needs and preferences.

Popular destinations

Best Midland holiday rentals with a balcony

Boho Hideaway W/ Hot Tub, Sauna & Games - Midland
10 6 reviews

Boho Hideaway W/ Hot Tub, Sauna & Games

apartment, Midland
This spacious five-bedroom, two-bathroom flat is located in the lakeside community of Midland, Ontario, offering immediate access to Georgian Bay and being just 3.2 kilometres from Balm Beach and 32 kilometres from Mount St. Louis Moonstone Ski Resort.
This property accommodates up to ten guests and boasts a private backyard with a six-seater hot tub, a games room with multiple entertainment options, two fully equipped kitchens, and direct access to kayaking, hiking, and biking trails.
Luxury Georgian Bay Gem, Heated Pool! Hot Tub, Close To Trails & Lake - Midland
10 1 review

Luxury Georgian Bay Gem, Heated Pool! Hot Tub, Close To Trails & Lake

apartment, Midland
This seven-bedroom house is located in the mountains of Midland, just 2 km from Lake Huron, Georgian Bay, and Martyrs' Shrine, offering stunning views and easy access to local attractions. It has received excellent user ratings, making it a popular choice for travellers.
The property can accommodate up to 14 guests and features a fully equipped kitchen, a private pool, a jacuzzi, a terrace, a garden, and an arcade/game room, providing a comfortable and entertaining stay for families and groups.
Cheerful 4-bedroom Cottage In Nature Setting - Midland
9.7 63 reviews

Cheerful 4-bedroom Cottage In Nature Setting

house, Tay
This charming cottage is situated just 8 kilometres from the town of Waubaushene and a short walk from the southeast shore of Georgian Bay, offering easy access to both the stunning beauty of the area and the Tay Shore Trails. It has received excellent user, location, and cleanliness ratings.
The 139 square metre cottage has four bedrooms and one bathroom, comfortably accommodating up to eight guests. The well-equipped kitchen, spacious living area with a fireplace, large backyard deck, and access to a fire pit, plus a 65-inch Smart TV, air conditioning, and fast internet, make this a perfect choice for families looking for a relaxing getaway.
Beautiful Luxury Lake Front Cottage Georgian Bay - Midland
10 39 reviews

Beautiful Luxury Lake Front Cottage Georgian Bay

cottage, Georgian Bay
This waterfront property is located near Georgian Bay, just steps from Lake Huron, and within 20 kilometres of Georgian Bay Islands National Park and Six Mile Lake, offering a peaceful retreat for nature lovers. This cottage has consistently received excellent ratings for its location, cleanliness, and overall experience.
The accommodation is spacious, spanning 214 square metres, and features a private balcony, fireplace, and a fully equipped kitchen. Guests can enjoy a range of activities including swimming, kayaking, hiking, and exploring the nearby national park, all while staying connected with free Wi-Fi.

Best pet friendly Midland holiday rentals

Among the 198 accommodations in Midland, here are the 4 best pet friendly rentals

Newly Renovated Beachfront 2 Bdrm W/ Patio! - Midland
9.7 15 reviews

Newly Renovated Beachfront 2 Bdrm W/ Patio!

house, Midland
The Beausoleil Suite, a two-bedroom apartment sleeping six, is situated on Georgian Bay, a short drive (approx. 24km) from Midland, offering easy access to Balm Beach (24km), Awenda Provincial Park (42km), and Wasaga Beach (53km).
This lakeside property boasts 82 metres of stunning shoreline, a private patio, a fully equipped kitchen with BBQ, shared access to water toys, and a 10% discount at Diverse Rentals marina; modern amenities include a smart TV and central heating and air conditioning.
Chateau Champlain Cottage - Midland
9.1 13 reviews

Chateau Champlain Cottage

apartment, Penetanguishene
This waterfront property is conveniently located in Midland, just 5km from Copeland Creek Wetlands Trail Trailhead, Awenda Provincial Park, and Penetanguishene Rotary Park, offering easy access to nature and outdoor activities. The property has received excellent user ratings for its location, cleanliness, and overall experience.
The house has 3 bedrooms and 2 bathrooms, comfortably accommodating up to 8 guests. Enjoy a game room, a garden with barbecue facilities, a patio, and a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher.
Nearskiingmount Gorgeous Cottage - Midland
8.3 6 reviews

Nearskiingmount Gorgeous Cottage

apartment, Tay
This Tay dwelling offers direct access to the Tayshore Trail along Georgian Bay, with ski resorts like Mt. St. Louis just 22 kilometres away and Horseshoe Valley 40 kilometres away, all within a 5-10 minute drive of Highway 400 and essential amenities.
This five-bedroom property accommodates up to 16 guests with air conditioning, Wi-Fi, and a microwave, featuring an open-concept living area, an outdoor fire pit, and proximity to Wye Marsh Conservation, Awenda Provincial Park, and Wasaga Beach.
Chit Chat - Beach Lakefront Cabin On Georgian Bay - Midland
9.3 6 reviews

Chit Chat - Beach Lakefront Cabin On Georgian Bay

cabin, Tiny
Chit Chat is a modern lodge situated on Georgian Bay in Tiny, part of a family cottage compound offering a prime waterfront experience.
This comfortable lodge accommodates eight guests with two bathrooms, features air conditioning, internet, and a kitchen, making it ideal for a relaxed cottage getaway.
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