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Midland cottages
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21 Best cottages in Midland

Search Cottages near the Old Town in Midland

Navigate local attractions easily on foot from centrally positioned cottages in Midland, putting historic districts steps away.

The Relaxation Station - Midland
10 11 reviews

The Relaxation Station

cottage, Tiny
This waterfront cottage in Tiny offers a prime location, just a 6-minute walk to Awenda Provincial Park and a 15-minute drive to Discovery Harbour.
This 950 square foot rental accommodates up to 10 guests with 3 bedrooms and 1 bathroom, featuring a full kitchen, air conditioning, free Wi-Fi, and on-site water sports equipment.
Gorgeous Winfield Chalet Cottage - Midland
9.9 91 reviews

Gorgeous Winfield Chalet Cottage

cottage, Midland
The Winfield Chalet is a cozy cottage located in Victoria Harbour, just a short distance from Midland, with easy access to the Georgian Bay, the Tay Trail, and local amenities. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
This charming vacation rental features 3 bedrooms and 1 bathroom, comfortably accommodating up to 9 guests. The cottage provides a variety of amenities for a relaxing and enjoyable stay, including a heated garage with games, an above-ground pool, a trampoline, a swing set, and a fire pit.
Stylish Sandy Beach 4-bed Waterfront - Midland
9.8 11 reviews

Stylish Sandy Beach 4-bed Waterfront

cottage, Tiny
This Tiny, Ontario waterfront vacation home is a 10-minute walk from Lake Huron and Georgian Bay, and within 9 miles of the Midland Golf and Country Club and Copeland Creek Wetlands Trail.
This 3000-square-foot family-friendly retreat boasts four bedrooms, three bathrooms, sleeps eight, and includes a fully equipped kitchen, jacuzzi, sauna, tennis court, game room, and private balcony.
Luxury 4br Lakefront Cottage W/ Sauna & Dock! - Midland
10 2 reviews

Luxury 4br Lakefront Cottage W/ Sauna & Dock!

cottage, Midland
This waterfront cottage in Tay offers direct lake access and is approximately a 15-20 minute drive to Midland's cultural attractions, including the Huronia Museum and Sainte-Marie among the Hurons.
This pet-friendly, family-friendly rental spans 2480 square feet, accommodating up to 10 guests with 4 bedrooms and 3 bathrooms, featuring a modern kitchen with a wine fridge, a private dock, a wood-burning barrel sauna, and outdoor living spaces with a fire pit and BBQ.

Top Family-Friendly Cottages in Midland

Kid-friendly cottages in Midland place city attractions within easy reach, making for a stress-free family vacation.

Luxury 4br Lakefront Cottage W/ Sauna & Dock! - Midland
10 2 reviews

Luxury 4br Lakefront Cottage W/ Sauna & Dock!

cottage, Midland
This waterfront cottage in Tay offers direct lake access and is approximately a 15-20 minute drive to Midland's cultural attractions, including the Huronia Museum and Sainte-Marie among the Hurons.
This pet-friendly, family-friendly rental spans 2480 square feet, accommodating up to 10 guests with 4 bedrooms and 3 bathrooms, featuring a modern kitchen with a wine fridge, a private dock, a wood-burning barrel sauna, and outdoor living spaces with a fire pit and BBQ.
The Relaxation Station - Midland
10 11 reviews

The Relaxation Station

cottage, Tiny
This waterfront cottage in Tiny offers a prime location, just a 6-minute walk to Awenda Provincial Park and a 15-minute drive to Discovery Harbour.
This 950 square foot rental accommodates up to 10 guests with 3 bedrooms and 1 bathroom, featuring a full kitchen, air conditioning, free Wi-Fi, and on-site water sports equipment.
Stylish Sandy Beach 4-bed Waterfront - Midland
9.8 11 reviews

Stylish Sandy Beach 4-bed Waterfront

cottage, Tiny
This Tiny, Ontario waterfront vacation home is a 10-minute walk from Lake Huron and Georgian Bay, and within 9 miles of the Midland Golf and Country Club and Copeland Creek Wetlands Trail.
This 3000-square-foot family-friendly retreat boasts four bedrooms, three bathrooms, sleeps eight, and includes a fully equipped kitchen, jacuzzi, sauna, tennis court, game room, and private balcony.
Gorgeous Winfield Chalet Cottage - Midland
9.9 91 reviews

Gorgeous Winfield Chalet Cottage

cottage, Midland
The Winfield Chalet is a cozy cottage located in Victoria Harbour, just a short distance from Midland, with easy access to the Georgian Bay, the Tay Trail, and local amenities. It has consistently received excellent ratings for location, cleanliness, and overall user experience.
This charming vacation rental features 3 bedrooms and 1 bathroom, comfortably accommodating up to 9 guests. The cottage provides a variety of amenities for a relaxing and enjoyable stay, including a heated garage with games, an above-ground pool, a trampoline, a swing set, and a fire pit.

Frequently Asked Questions about cottages in Midland

  • What would be a good 2-days itinerary for visiting Midland?

    On your first day, check out the Midland Bay Marina and enjoy the views of Georgian Bay. Then, head over to the Huronia Museum to learn about the history of the area. On day two, spend some time at the Midland Cultural Centre for some entertainment, and afterwards, take a stroll along the waterfront trail for some fresh air.
  • What are the best cottages in Midland?

  • What part of Midland is ideal for renting a cottage?

    The best spots for cottages are along the shores of Georgian Bay, especially around the areas of Little Lake and the Penetanguishene Road. You'll find plenty of options with stunning views and easy access to water activities.
  • What are the best cottages with a pool in Midland?

  • When is the best time to rent a cottage in Midland?

    The peak season for cottage rentals in Midland is during the summer months, from June to August. However, if you prefer a quieter experience, spring and fall offer pleasant weather and fewer crowds.
  • What are the best cottages with a jacuzzi in Midland?

  • What are the can't-miss sights in Midland?

    You have to visit the Midland Bay Marina, the Huronia Museum, and the Midland Cultural Centre. The waterfront trail is a must-do for a scenic walk or bike ride, and don't forget to check out the historic Steamship Midland for a glimpse into the past.
  • What are the best cottages for families and kids in Midland?

  • Why consider renting a cottage in Midland for your stay?

    Renting a cottage in Midland gives you the opportunity to experience the beauty of Georgian Bay firsthand. You can enjoy swimming, boating, fishing, and relaxing in a peaceful setting. Plus, it's a great way to escape the city and reconnect with nature.
  • What are the best pet friendly cottages in Midland?

  • Can you easily explore Midland on foot or by bike?

    Midland is a very walkable city, especially the downtown area. You can easily explore the shops, restaurants, and attractions on foot. If you want to venture further, the waterfront trail is perfect for a leisurely bike ride.
  • What are the best cottages with parking in Midland?

  • What are the best restaurants in Midland with nature views?

    Try the The Docks Restaurant & Bar, with its stunning views of the marina, or The Wooden Paddle for a more casual dining experience with a patio overlooking the water. Both offer delicious food and breathtaking scenery.
  • What family-friendly activities are available in Midland?

    Midland has plenty of family-friendly activities, like visiting the Huronia Museum, taking a boat tour on Georgian Bay, or enjoying a picnic at the park. The splash pad at the waterfront is a big hit with kids, and the Midland Cultural Centre often hosts children's shows and events.

Popular destinations

Guest-Favorite Cottages with a Hot Tub in Midland

A private hot tub at your cottage makes every trip to Midland truly unforgettable after a day in the city.

Forest Oasis In Tay W/large Jacuzzi Hottub - Midland
9.7 103 reviews

Forest Oasis In Tay W/large Jacuzzi Hottub

cottage, Midland
This charming cottage is located just a short drive from Midland, offering easy access to the beautiful Georgian Bay and the quaint town's amenities. The cottage consistently receives excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
The three-bedroom cottage comfortably sleeps six guests and features a fully equipped kitchen, a cozy living area, and a private backyard with a hot tub. Enjoy year-round relaxation with access to a private swimming area, kayaks, paddleboards, a fire pit, and a Nintendo Switch, making it perfect for families and groups seeking a memorable getaway.
Stylish Sandy Beach 4-bed Waterfront - Midland
9.8 11 reviews

Stylish Sandy Beach 4-bed Waterfront

cottage, Tiny
This Tiny, Ontario waterfront vacation home is a 10-minute walk from Lake Huron and Georgian Bay, and within 9 miles of the Midland Golf and Country Club and Copeland Creek Wetlands Trail.
This 3000-square-foot family-friendly retreat boasts four bedrooms, three bathrooms, sleeps eight, and includes a fully equipped kitchen, jacuzzi, sauna, tennis court, game room, and private balcony.

Best Midland cottages with a kitchen

Forest Oasis In Tay W/large Jacuzzi Hottub - Midland
9.7 103 reviews

Forest Oasis In Tay W/large Jacuzzi Hottub

cottage, Midland
This charming cottage is located just a short drive from Midland, offering easy access to the beautiful Georgian Bay and the quaint town's amenities. The cottage consistently receives excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
The three-bedroom cottage comfortably sleeps six guests and features a fully equipped kitchen, a cozy living area, and a private backyard with a hot tub. Enjoy year-round relaxation with access to a private swimming area, kayaks, paddleboards, a fire pit, and a Nintendo Switch, making it perfect for families and groups seeking a memorable getaway.
The Relaxation Station - Midland
10 11 reviews

The Relaxation Station

cottage, Tiny
This waterfront cottage in Tiny offers a prime location, just a 6-minute walk to Awenda Provincial Park and a 15-minute drive to Discovery Harbour.
This 950 square foot rental accommodates up to 10 guests with 3 bedrooms and 1 bathroom, featuring a full kitchen, air conditioning, free Wi-Fi, and on-site water sports equipment.
Stylish Sandy Beach 4-bed Waterfront - Midland
9.8 11 reviews

Stylish Sandy Beach 4-bed Waterfront

cottage, Tiny
This Tiny, Ontario waterfront vacation home is a 10-minute walk from Lake Huron and Georgian Bay, and within 9 miles of the Midland Golf and Country Club and Copeland Creek Wetlands Trail.
This 3000-square-foot family-friendly retreat boasts four bedrooms, three bathrooms, sleeps eight, and includes a fully equipped kitchen, jacuzzi, sauna, tennis court, game room, and private balcony.
Luxury 4br Lakefront Cottage W/ Sauna & Dock! - Midland
10 2 reviews

Luxury 4br Lakefront Cottage W/ Sauna & Dock!

cottage, Midland
This waterfront cottage in Tay offers direct lake access and is approximately a 15-20 minute drive to Midland's cultural attractions, including the Huronia Museum and Sainte-Marie among the Hurons.
This pet-friendly, family-friendly rental spans 2480 square feet, accommodating up to 10 guests with 4 bedrooms and 3 bathrooms, featuring a modern kitchen with a wine fridge, a private dock, a wood-burning barrel sauna, and outdoor living spaces with a fire pit and BBQ.

Traveler-Approved Pet-Friendly Cottages in Midland

No need to leave your dog behind; each Midland cottage on this list offers nearby dog parks and easy city walks.

Luxury 4br Lakefront Cottage W/ Sauna & Dock! - Midland
10 2 reviews

Luxury 4br Lakefront Cottage W/ Sauna & Dock!

cottage, Midland
The Relaxation Station - Midland
10 11 reviews

The Relaxation Station

cottage, Tiny
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