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

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.
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.
Cozy Beachside Getaway  Steps From Balm Beach! - Midland
10 2 reviews

Cozy Beachside Getaway Steps From Balm Beach!

cottage, Tiny
This holiday home is located in Tiny, mere steps from Balm Beach and within a 10-minute drive of Midland and Penetanguishene.
This 27-square-metre lodge accommodates four guests across two bedrooms and one bathroom, featuring a fully equipped kitchen, air conditioning, WiFi, a garden with a fire pit and BBQ, a sunroom with lake views, and a 10% discount offer on a Georgian Spirit Cruise from Midland.
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

Cozy Georgian Bay Getaway In Midland - Midland
9.3 11 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.
Forever Memories - Midland
9.0 2 reviews

Forever Memories

cabin, Midland
This new log lodge in Midland offers a peaceful escape, conveniently located a short drive from Penetanguishene and Midland's attractions.
This four-bedroom, four-bathroom property accommodates up to ten guests and features air conditioning, internet, a kitchen, and a jacuzzi, making it ideal for family holidays.
Home Grandview - Midland
10 32 reviews

Home Grandview

apartment, Midland
This magnificent four-bedroom, three-bathroom house in Magnus Beach, Midland, boasts stunning Georgian Bay views and is situated a short distance from Midland's resorts and parks.
The 3,400 sq ft property offers ample space for nine guests, featuring a fully equipped kitchen, sunroom, pool table, Weber BBQ, infrared sauna, fire pit, high-speed WiFi (1.5Gb), a three-car garage with Level 2 EV charger, and a tranquil garden.
New Guest House + Hobby Farm Stay+ Walking Trails - Midland
10 4 reviews

New Guest House + Hobby Farm Stay+ Walking Trails

gîte, Tay
This private, furnished 56 square meter gîte is located on an 8-acre hobby farm in Tay, a 16-24 minute drive from Midland, Penetanguishene, and Elmvale, offering a peaceful rural escape.
This accommodation sleeps up to three guests and features a sleeping loft accessible by ladder, a kitchen with a fridge, freezer, and microwave, and access to walking trails, a shared firepit, and nearby snowmobile and ski trails at Mount St. Louis Moonstone.

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

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.
Rawley Resort, Spa & Marina, Trademark Collection By Wyndham - Midland
9.0 154 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.
Victoria Harbour Cottages - Midland
9.3 29 reviews

Victoria Harbour Cottages

house, Midland
Victoria Harbour Cottages are located on the beachfront in Victoria Harbour, just 5.5 miles from Tay River Basin and 29 miles from Lake Simcoe Regional Airport. The cottages have received excellent ratings for location, cleanliness, and overall experience.
These one-bedroom cottages offer a comfortable and convenient stay for travellers. Enjoy the on-site amenities, including a fully equipped kitchen, private balconies, and access to free bikes for exploring the beautiful surroundings.
The Lake House! Private 3.6 Acres Family Retreat! - Midland
9.9 84 reviews

The Lake House! Private 3.6 Acres Family Retreat!

cottage, Georgian Bay
This five-bedroom holiday home is located on the shores of Georgian Bay, just 6km from Lake Huron and a 24km drive from Six Mile Lake Provincial Park.
The 297 square metre property boasts a fully-equipped kitchen, a terrace, a garden, and a playground, making it ideal for families and groups of up to 12 guests.

Best pet friendly Midland holiday rentals

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

Georgian Bay Water/beach Front Cottage - Midland
9.9 60 reviews

Georgian Bay Water/beach Front Cottage

apartment, Midland
This apartment is located in Midland, Ontario, directly across the street from the Trans Canada Trail and a short walk from Rotary Park, offering access to the waterfront and Georgian Bay. The apartment has received excellent ratings for location, cleanliness and user experience.
The property has three bedrooms and one bathroom, accommodating up to seven guests. Amenities include a fully equipped kitchen, air conditioning, a garden, parking, internet access, and a fireplace. Guests can also enjoy the nearby Trans Canada Trail for biking and walking, as well as the beach, skate park, basketball court, and splash pad at Rotary Park.
Up To 40% Sale Near-skiing-mount Gorgeous Cottage - Midland
8.6 24 reviews

Up To 40% Sale Near-skiing-mount Gorgeous Cottage

apartment, Tay
This five-bedroom Tay holiday home, near Georgian Bay, offers easy access to Highway 400 and lies within 22-40km of Mount St. Louis and Horseshoe Valley ski resorts.
Sleeping up to 19 guests, the property boasts an open-plan living area with pine ceilings, a fully equipped kitchen including a Brita filter, air conditioning, Wi-Fi, a fire pit, and direct access to the Tay Shore Trail; pets are welcome.
Life's A Beach House -Perfect Beachfront Vacation Rental - Midland
10 1 review

Life's A Beach House -Perfect Beachfront Vacation Rental

apartment, Tiny
This beachfront flat in Tiny offers direct access to Balm Beach, situated just a short walk from local amenities and within proximity to Lake Huron and Georgian Bay.
Accommodating up to seven guests across three bedrooms, this property features a patio with sunset views, a fire pit, and is ideal for those seeking beach access, swimming, and paddleboarding opportunities.
Beautiful Waterfront Cottage On Georgian Bay - Midland
9.9 17 reviews

Beautiful Waterfront Cottage On Georgian Bay

apartment, Midland
This waterfront holiday home is located on Georgian Bay, just a short distance from Midland, offering easy access to shops, restaurants, and a range of outdoor activities. The property has received excellent ratings for location, cleanliness, and overall user experience.
This three-bedroom cottage can comfortably accommodate up to nine guests. Enjoy a range of amenities including a private sandy beach, kayaks and paddle boards, a fire pit, BBQ, high-speed internet, a TV, and a jacuzzi.
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