Holiday Rentals in Midland

115 available vacation rental offers

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Midland holiday rentals
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115 Holiday rentals and Airbnb in Midland

Best family friendly Midland holiday rentals

Among the 115 accommodations in Midland, here are the 4 best family friendly rentals

Sandy Beach/boating/swimming/hot Tub/marina/trails - Midland
8.8 50 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.
3-bedroom Lakeview Cottage With Resort Amenities! - Midland
10 1 review

3-bedroom Lakeview Cottage With Resort Amenities!

apartment, Severn
This newly renovated three-bedroom stone cottage is located adjacent to Christie's Mill Inn and Spa in Severn, offering exclusive access to the resort's extensive amenities.
This family-friendly accommodation, which accommodates up to six guests, features a fully equipped kitchen, air conditioning, a swimming pool, jacuzzi, garden, sauna, and fitness centre, with nearby opportunities for water activities and dining at the resort's restaurant and patio.
The Relaxation Station - Midland
10 11 reviews

The Relaxation Station

cottage, Tiny
This waterfront holiday home in Tiny, Ontario, is situated 550 metres from Awenda Provincial Park and a 15-minute drive from Discovery Harbour.
This 88 square metre cottage accommodates up to 10 guests across 3 bedrooms and features a private terrace with barbecue, air conditioning, and on-site watersports equipment, with free Wi-Fi and parking provided.
Spacious 6-bdrm Luxury, Modern House With Lake View In Cottage Country, Ontario - Midland
9.8 9 reviews

Spacious 6-bdrm Luxury, Modern House With Lake View In Cottage Country, Ontario

apartment, Victoria Harbour
This six-bedroom Tay holiday home, sleeping up to 16 guests, is situated within 10km of Martyrs' Shrine, Sainte-Marie among the Hurons, and the Wye Marsh Wildlife Centre, offering easy access to Midland's key attractions.
The property boasts a fully equipped kitchen, three bathrooms, a jacuzzi, fitness centre, and parking; enjoy on-site amenities including a barbecue and Smart TV, perfect for a relaxing family getaway.

Best Midland holiday rentals with parking

Cozy Georgian Bay Getaway In Midland - Midland
9.6 5 reviews

Cozy Georgian Bay Getaway In Midland

apartment, Midland
This one-bedroom flat is located in Midland, offering convenient access to Georgian Bay.
This comfortable accommodation for two guests features a fully equipped kitchen, air conditioning, and Wi-Fi, making it ideal for exploring the local area or for business trips.
Mcgibbon By The Bay-the Annex - Midland
9.7 20 reviews

Mcgibbon By The Bay-the Annex

resort, Midland
This apartment is situated in the historic town of Penetanguishene, just 10 kilometres from Midland, offering a charming and peaceful setting on the shores of Georgian Bay. It has consistently received excellent ratings for location, cleanliness, and overall guest experience.
The apartment is a one-bedroom property, comfortably accommodating up to two guests. It features a fully equipped kitchenette, modern amenities like a large flat-screen television and smart TVs, and easy access to local attractions, outdoor activities, and day trips to nearby destinations.
By The Bay Spacious One Bedroom - Midland
10 107 reviews

By The Bay Spacious One Bedroom

apartment, Midland
This one-bedroom apartment is located in Midland, just a short walk from the beach, waterfront restaurants, and theatres. The property has received excellent ratings for its location, cleanliness, and overall experience.
The apartment is suitable for two guests and features a comfortable bedroom with a queen-size bed, a spacious bathroom with a walk-in shower, and a fully equipped kitchen with a dishwasher, microwave, and a washer/dryer. Enjoy relaxing on the private deck or explore the nearby attractions.
Steps To Beach & Scenic Nature Trails -1.5h Fromto - Midland
9.9 68 reviews

Steps To Beach & Scenic Nature Trails -1.5h Fromto

apartment, Midland
This charming cottage is situated in Paradise Point, just across the road from Paterson Park and the beach on Georgian Bay, a peaceful area 145 kilometres from Toronto. The cottage consistently receives excellent ratings for its location, cleanliness, and overall experience.
The property offers two bedrooms and one bathroom, comfortably accommodating up to six guests. The cottage is fully equipped with a kitchen, a private garden with a fire pit and barbecue, and a garage for storing outdoor equipment, making it perfect for families or groups seeking a relaxing getaway.

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

Cheerful 4-bedroom Cottage In Nature Setting - Midland
9.7 61 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.
Georgian Bay 5 Bedroom Waterfront , Large Deck .Quiet Family Neighbourhood. - Midland
No reviews

Georgian Bay 5 Bedroom Waterfront , Large Deck .Quiet Family Neighbourhood.

apartment, Tay
This Tay apartment offers direct waterfront access to Georgian Bay within a quiet, family-friendly neighbourhood, situated close to the natural attractions of Lake Huron.
This spacious five-bedroom, two-bathroom flat boasts a large deck, garden access, on-site laundry, a jetted bathtub, smart TV, and complimentary Wi-Fi, ideal for those seeking a relaxing stay with ample amenities.
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.
Stylish Sandy Beach 4-bed Waterfront - Midland
9.8 6 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 115 accommodations in Midland, here are the 4 best pet friendly rentals

Duke's Point - Georgian Bay Island Cottage - Midland
No 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.
Antique Retreat Private Apt Midtown Midland - Midland
9.6 10 reviews

Antique Retreat Private Apt Midtown Midland

apartment, Midland
This two-bedroom flat is located in Mid-Midland, a short walk from the Midland Arena and Midland Cultural Centre, and less than 3 kilometres from the town centre.
The apartment offers a dedicated workspace for remote working, a fenced patio, and access to a swimming pool, making it ideal for families or groups of up to four.
1bdrm Rental In Victoria Harbour - Midland
No reviews

1bdrm Rental In Victoria Harbour

apartment, Midland
This one-bedroom apartment in Victoria Harbour, overlooking Georgian Bay and directly on the Tay Trail, offers easy access to Midland (16km), Orillia (40km), Barrie (64km), and Wasaga Beach (72km).
The self-contained basement flat sleeps two, includes private garage parking, Wi-Fi, and a kitchen, and is ideally located for exploring Georgian Bay cruises and nearby skiing opportunities.
Discounted Rates. Farm + Atv Trails + Fire Pit - Midland
9.0 2 reviews

Discounted Rates. Farm + Atv Trails + Fire Pit

apartment, Tay
This cabin is located in Tay, just five minutes from a major shopping centre and surrounded by forest, gardens, and fruit trees. It has excellent user, location and cleanliness ratings, making it a great choice for travellers.
The property spans seven acres and can accommodate up to ten guests. It features a fully equipped kitchen, a private trampoline and soccer field, a fire pit, a BBQ, and access to nearby bike, ATV, and snowmobile trails.
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