Holiday Rentals in Midland

198 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • hotelscom
  • vrbo
  • tripadvisor
  • expedia
  • tripcom
  • agoda
  • homestay
  • tuivillas
  • hostelworld
  • hotelopia
Midland holiday rentals
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

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.
The Quiet Escape - Midland
9.6 15 reviews

The Quiet Escape

bungalow, Midland
This one-bedroom flat is situated in a quiet neighbourhood in Midland, offering privacy and peaceful surroundings.
The apartment sleeps up to four guests and features a fully equipped kitchenette, a dining area, a queen-sized bed, and a pull-out sofa bed, providing ample space for relaxation and comfortable living.
Spacious 6-bdrm Luxury, Modern House With Lake View In Cottage Country, Ontario - Midland
9.8 10 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.
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.

Best Midland holiday rentals with parking

Georgian Bay Retreat - Apartment In Midland - Midland
9.7 72 reviews

Georgian Bay Retreat - Apartment In Midland

apartment, Midland
This basement flat is located in Midland, a short distance from Georgian Bay and the best sandy beaches in Ontario. The property has excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The self-contained suite has a separate bedroom with a queen-size bed, and can accommodate up to two guests. It comes with modern amenities, including unlimited internet, a full kitchen, a fireplace, a private garden area, and a washer and dryer, as well as being close to local attractions like Georgian Bay, the Midland Waterfront, and Little Lake Park.
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.
Charming Century Home W. Cottage Garden Suite - Midland
8.3 6 reviews

Charming Century Home W. Cottage Garden Suite

apartment, Midland
This historic Century home in Midland offers spectacular lake and escarpment views from a quiet hilltop, providing easy walking access to downtown Midland's shops, restaurants, festivals, and waterfront, as well as proximity to extensive hiking trail systems.
This four-bedroom holiday rental accommodates up to eight guests with versatile sleeping arrangements across the main house and a renovated garden suite, featuring a full kitchen with new appliances, air conditioning, a garden, and ample parking for four or more vehicles.
Waterfront Retreat | Sandy Beach, Kayak, Sup & A/c - Midland
9.7 56 reviews

Waterfront Retreat | Sandy Beach, Kayak, Sup & A/c

cabin, Midland
This off-grid bunkie is situated in a quiet campground on Georgian Bay, approximately 145 kilometres north of Toronto. The property is highly rated, with excellent reviews for its location, cleanliness, and overall user experience.
The bunkie is a cosy dwelling with a double bed in a loft, a sofa, a small fridge, and battery-powered lights. Guests can enjoy a range of amenities, including a shared sandy beach, a water pad, a canoe, a kayak, paddleboards, a fire pit, and a BBQ area.

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

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.
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.
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.
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.

Best pet friendly Midland holiday rentals

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

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.
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.
Your Happy Place - Midland
9.8 12 reviews

Your Happy Place

apartment, Midland
This four-bedroom, two-bathroom apartment in Port McNicoll, near Midland, Ontario, offers easy access to Georgian Bay's beaches and hiking trails.
Sleeping up to nine guests, this self-catering property features a fully equipped kitchen, air conditioning, parking, internet access, and a queen-size air mattress; nearby attractions require further investigation to determine precise distances.
Newly Renovated Beachfront 2 Bdrm W/ Patio! - Midland
9.7 15 reviews

Newly Renovated Beachfront 2 Bdrm W/ Patio!

house, Midland
The Beausoleil Suite, a two-bedroom apartment sleeping six, is situated on Georgian Bay, a short drive (approx. 24km) from Midland, offering easy access to Balm Beach (24km), Awenda Provincial Park (42km), and Wasaga Beach (53km).
This lakeside property boasts 82 metres of stunning shoreline, a private patio, a fully equipped kitchen with BBQ, shared access to water toys, and a 10% discount at Diverse Rentals marina; modern amenities include a smart TV and central heating and air conditioning.
©2026 cozycozy.com