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

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.
Cottage On Water At Oak Bay Gulf Club - Midland
9.8 6 reviews

Cottage On Water At Oak Bay Gulf Club

cottage, Port Severn
This Georgian Bay holiday home is situated a short distance from both Lake Huron and Georgian Bay, and 2.3 kilometres from the Oak Bay Golf Club.
Sleeping up to eight guests, this two-bedroom, two-bathroom property boasts a fully equipped kitchen, air conditioning, Wi-Fi, laundry facilities, a patio, and barbecue grills; enjoy on-site amenities and the nearby attractions of Georgian Bay.
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.
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.

Best Midland holiday rentals with parking

Victoria Harbour Cottages One Bedroom Chalet - Midland
9.7 71 reviews

Victoria Harbour Cottages One Bedroom Chalet

apartment, Midland
This charming cottage is situated on the shores of Georgian Bay, a short drive from Midland town centre and the bustling Midland Bay Marina. It has received excellent ratings for location, cleanliness and overall user experience.
The one-bedroom chalet offers a pull-out queen sofa bed, accommodating up to four guests. It features a fully equipped kitchen, a private deck and patio, and access to shared water equipment including a canoe, paddle boat and kayak.
Red Rustic Cabin By The Beach - Midland
No reviews

Red Rustic Cabin By The Beach

cabin, Midland
This 3-bedroom, 3-season cottage in Midland is located on the shores of Georgian Bay, offering exclusive access to a private, members-only beach directly across the street.
This pet-friendly lodge accommodates up to eight guests and features a kitchen with a fridge and microwave, air conditioning, a garden, parking, and a unique outdoor shower alongside an indoor powder room for an authentic cottage lifestyle experience.
Victoria Harbour Cottages Loft Chalet - Midland
9.6 80 reviews

Victoria Harbour Cottages Loft Chalet

apartment, Midland
This charming cottage is located on a peaceful inlet of Georgian Bay, just a short distance from the town of Midland, offering stunning sunsets over the water. The property has received excellent ratings from previous guests for its cleanliness, location, and overall experience.
The cottage features a modern kitchen, a private deck with a BBQ, and comfortable sleeping arrangements for up to four guests. Enjoy the option of a sleep loft, a king-size bed, and a pull-out sofa bed, perfect for families or couples seeking a relaxing getaway.
Weekly Midland Vacation Rental With Pool - Midland
8.8 15 reviews

Weekly Midland Vacation Rental With Pool

apartment, Midland
This comfortable apartment is located in Midland, just 200 metres from Georgian Bay and 100 metres from a lively area with restaurants and shops. It has received excellent ratings for its location, cleanliness, and user experience.
The property has three bedrooms, two bathrooms, a spacious kitchen, a living/dining room, a TV/games room, and a large deck with a barbecue. Guests can enjoy a private backyard, access to a swimming pool, and a peaceful atmosphere with friendly neighbours.

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

Beautiful Luxury Lake Front Cottage Georgian Bay. - Midland
10 39 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.
Private Family Retreat! 
Now Open For Summer 2026! - Midland
9.9 84 reviews

Private Family Retreat! Now Open For Summer 2026!

apartment, 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.
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.
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.

Best pet friendly Midland holiday rentals

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

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.
Hideaway Retreat Bungalow W/ Hot Tub - Midland
9.8 8 reviews

Hideaway Retreat Bungalow W/ Hot Tub

apartment, Midland
This cosy bungalow is located in Midland, just 5 kilometres from the shores of Georgian Bay and Balm Beach, and a short distance from the town centre. The property enjoys excellent user, location and cleanliness ratings, making it a popular choice for travellers.
The bungalow offers 3 bedrooms and 1 bathroom, comfortably accommodating up to 6 guests. Amenities include a private hot tub with gazebo, a large deck with fire table and BBQ, a fire pit with Muskoka chairs, kayaks for guest use, a fully equipped kitchen, air conditioning, and a garden.
Perfect Summer Gateway.lots To Do Here - Midland
9.7 69 reviews

Perfect Summer Gateway.lots To Do Here

apartment, Midland
This charming cottage is located on the southern tip of Georgian Bay in Victoria Harbour, just 160 kilometres from the Greater Toronto Area, offering a tranquil escape surrounded by the beauty of Georgian Bay.
The cottage comfortably accommodates up to six guests and features a well-equipped kitchen, a cosy living room, two bathrooms, and a games room with a pool table. Guests can enjoy a private garden, a fire pit, and a year-round hot tub, as well as access to a range of outdoor activities in the area.
Georgian Grace/3bdr/5 Person - Midland
No reviews

Georgian Grace/3bdr/5 Person

apartment, Midland
This Georgian Bay cottage provides direct beach access with unparalleled sunset views, situated a short drive from Midland's downtown amenities.
This three-bedroom, one-bathroom property accommodates up to five guests and features a kitchen, air conditioning, and parking, offering a tranquil natural setting with a deck for enjoying the waterfront.
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