Holiday Rentals in Midland

198 available vacation rental offers

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Midland holiday rentals
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Best Holiday rentals and Airbnb offers in Midland

Best family friendly Midland holiday rentals

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

Rawley Resort, Spa & Marina, Trademark Collection By Wyndham - Midland
9.0 165 reviews

Rawley Resort, Spa & Marina, Trademark Collection By Wyndham

resort, Severn
Rawley Resort, Spa & Marina is located in Port Severn, just 16 miles from the Tay River Basin and 30 miles from Casino Rama, offering easy access to the picturesque landscapes of the surrounding area. The resort has received very good user ratings, with excellent location and cleanliness scores.
The hotel offers a range of facilities, including a spa, a sauna, a hot tub, a marina, a restaurant, a bar, and a fitness centre. Guests can enjoy a variety of activities, such as hiking, skiing, cycling, boating, and water sports.
Modern 4br Cottage, Hot Tub & Sauna On Tay Trail - Midland
9.4 242 reviews

Modern 4br Cottage, Hot Tub & Sauna On Tay Trail

house, Tay
This four-bedroom house is located in Waubaushene, just 19 kilometres from Orillia Community Centre Arena and 12 kilometres from Midland Cultural Centre. The area offers a peaceful setting with easy access to Georgian Bay, trails, and nearby attractions. This property has received excellent user ratings for location, cleanliness, and overall experience.
This spacious 111 square metre property comfortably accommodates up to eight guests. The house is equipped with modern amenities including a fully equipped kitchen, a fireplace, a hot tub, a sauna, a tennis court, and a private garden, making it ideal for families and groups seeking a relaxing and enjoyable stay.
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.
Luxury 4br Lakefront Cottage W/ Sauna & Dock! - Midland
10 1 review

Luxury 4br Lakefront Cottage W/ Sauna & Dock!

cottage, Midland
This waterfront holiday home in Tay offers direct access to shallow waters via a private dock and is located approximately 1.6 to 2.4 kilometres from the Huronia Museum and Ste-Marie among the Hurons.
This spacious 230 square metre lodge comfortably accommodates up to 10 guests across four bedrooms, featuring a modern kitchen with a wine fridge, a gas fireplace, a wood-burning barrel sauna, kayaks, and parking for seven vehicles.

Best Midland holiday rentals with parking

Float Cabin On Georgian Bay 2 - Midland
No reviews

Float Cabin On Georgian Bay 2

barge
This unique floating cabin accommodation is situated on Georgian Bay, offering a serene waterfront experience just 500 meters from marina amenities.
This houseboat accommodates up to two guests and features a private bathroom, a Queen and Single bunk bed, a private deck with bay views, and access to an outdoor swimming pool and BBQ gazebo.
Sandy Beach/boating/swimming/hot Tub/marina/trails - Midland
8.9 59 reviews

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

apartment, 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.
10 Acre Romantic Country Retreat - Midland
No reviews

10 Acre Romantic Country Retreat

apartment, Tiny
This charming country retreat is located just a short five-minute drive from the stunning Georgian Bay, offering easy access to its beautiful waters and recreational activities. The surrounding area is peaceful and tranquil, perfect for escaping the hustle and bustle of city life.
The cottage offers three bedrooms and two bathrooms, comfortably accommodating up to eight guests. It is well-equipped with a kitchen, air conditioning, and a cosy fireplace, as well as outdoor amenities like parking and a fire pit, perfect for enjoying evenings under the stars.
Guest Unit - Midland
9.8 30 reviews

Guest Unit

house, Midland
This brand-new, three-bedroom self-catering apartment in Midland, Ontario, is located minutes from Georgian Bay, offering easy access to water activities and scenic trails.
The 3-bathroom property sleeps six guests and boasts modern amenities including air conditioning, parking, and Wi-Fi, alongside a comfortable and stylish layout perfect for families.

Frequently asked questions about holiday rentals in Midland

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

    The Discovery Harbour Museum is a great place for families, it has interactive exhibits and historical ships. The Midland Bay Landing is also a good option, with a playground and splash pad.
  • What are the best Airbnb and vacation rentals in Midland?

    The Haunted House Apt 302, Nest By The Bay - Downtown Midland / Private Loft and Perch By The Bay - Downtown Midland / Private Loft are the most popular Airbnb and vacation rentals in Midland among travelers.

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

    The summer months are the busiest, so book your vacation rental early if you want to visit during July or August. If you're looking for a quieter time, spring or autumn are good options.
  • What are the most popular Airbnbs in Midland?

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

    The Midland Waterfront Festival in July is a big one, with live music, food vendors, and activities for all ages. The annual Santa Claus Parade in December is also popular.
  • What are the best vacation rentals with a pool in Midland?

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

    A walk along the waterfront is always free and offers lovely views. The Midland Public Library is a great place to spend a few hours, and it's completely free.
  • What are the best rentals for families and kids in Midland?

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

    The Ship & Anchor Pub is a great place to try some classic Canadian dishes. If you're looking for something a bit fancier, The Wooden Nickel Restaurant is a popular spot.
  • 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 great option for a walk or bike ride, it stretches for several kilometres along the shore. The Simcoe County Greenbelt is also a good option for a longer cycle.
  • Are there pet-friendly attractions in Midland?

    The waterfront park is pet-friendly, and many restaurants have outdoor patios where you can bring your dog. The Midland Bay Landing also has a dog park.
  • What are the benefits of choosing a vacation rental in Midland?

    Vacation rentals offer more space and privacy than a hotel room. They're also a good option for families or groups of friends travelling together.
  • What are the top sports attractions and facilities in Midland?

    Midland has a great sports scene, with the Midland Midgets hockey team and the Midland Mariners baseball team. The town also has a public swimming pool, a community centre with a gym, and several parks with sports fields.

Popular destinations

Best Midland holiday rentals with a balcony

Private Lakehouse Getaway Hot Tub On The Water - Midland
No reviews

Private Lakehouse Getaway Hot Tub On The Water

house, Tay
This holiday let is located in a district of Tay providing easy access to local attractions and amenities, with key landmarks and attractions within easy reach.
This 186 square meter holiday home accommodates up to 23 guests and features a fully equipped kitchen, two bathrooms, free high-speed WiFi, and complimentary private parking, with a private balcony for enjoying the Tay atmosphere.
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 Retreat Heated Pool, Hot Tub, Sauna + Trails Near The Lake - Midland
10 1 review

Luxury Georgian Bay Retreat Heated Pool, Hot Tub, Sauna + Trails Near The 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.
Stylish Sandy Beach 4-bed Waterfront - Midland
9.6 10 reviews

Stylish Sandy Beach 4-bed Waterfront

cottage, Tiny
This family-friendly Tiny lakeside retreat, a 10-minute walk from Lake Huron and Georgian Bay, is situated within 15km of the Midland Golf and Country Club and Copeland Creek Wetlands Trail.
This 279 square metre property boasts four bedrooms, three bathrooms, sleeping eight guests, and features a fully equipped kitchen, jacuzzi, sauna, tennis court, and free Wi-Fi.

Best pet friendly Midland holiday rentals

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

Boho Hideaway W/ Hot Tub, Sauna & Games - Midland
9.9 74 reviews

Boho Hideaway W/ Hot Tub, Sauna & Games

bungalow, Midland
This bungalow is located in Midland, just a few kilometres from the town centre and Georgian Bay, with easy access to the Mount St. Louis Moonstone Ski Resort within a 30-minute drive. It has received excellent ratings for its location, cleanliness, and user experience.
This spacious property offers five bedrooms, two kitchens, and two living areas, comfortably accommodating up to ten guests. Amenities include a private hot tub and sauna, a large garden with a gazebo, fire pit, and BBQ, and a game room with a multi-functional table for foosball, pool, ping pong, shuffleboard, and bowling.
Just Loafin, Georgian Bay / Muskoka Area Cottage - Midland
9.8 46 reviews

Just Loafin, Georgian Bay / Muskoka Area Cottage

apartment, Tiny
This three-bedroom, three-bathroom holiday home in Tiny, Ontario, boasts stunning shoreline access with a private beach and boat ramp.
The property offers a fully equipped kitchen, including a dishwasher, central air conditioning, and a tennis court, accommodating up to eight guests and providing access to various water toys.
2 Bdrm Waterfront Retreat - Huge Beach! - Midland
9.1 16 reviews

2 Bdrm Waterfront Retreat - Huge Beach!

house, Midland
The White Cloud Suite, a three-bedroom apartment near Midland, Ontario, boasts 270 feet (approximately 82 metres) of Georgian Bay shoreline, providing direct beach access and is 24km from Balm Beach Provincial Park.
This pet-friendly self-catering property sleeps five, features a fully equipped kitchen with BBQ, a basement games area with ping pong and smart TV, and offers access to shared kayaks, paddleboards, and water trampolines, plus a 10% discount at Diverse Rentals marina.
Beautiful Luxury Lake Front Cottage Georgian Bay. - Midland
10 40 reviews

Beautiful Luxury Lake Front Cottage Georgian Bay.

apartment, 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.
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