This one-bedroom flat is located in Penetang, a picturesque town just 15 kilometres from Midland, offering easy access to the shores of Lake Simcoe and its charming downtown area. The self-catering accommodation features a fully equipped kitchen, air conditioning and a private garden, perfect for families or couples seeking a peaceful retreat.
10 13 reviews
Midland
10/07 – 12/07
SG$464/nighttotal: SG$928 (2 )
Newly Renovated Beachfront 2 Bdrm W/ Patio!
1 2
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.
8.8 3 reviews
Midland
03/09 – 20/12
SG$159/nighttotal: SG$17172 (108 )
Charming Cottage 2 Min Walk From A Private Beach On Georgian Bay
3 1
cottage , Port McNicoll
This charming three-bedroom cottage is located in Tay, Ontario, just five minutes' walk from Lake Huron and Georgian Bay, offering easy access to stunning natural landscapes. It has received very good user ratings. The cottage comfortably sleeps six guests and provides a range of amenities including Wi-Fi, air conditioning, towels, and linens. Guests can enjoy a short drive to Little Lake Park (11km) and Cawaja Beach (24km) for a variety of outdoor activities and entertainment.
9.5 36 reviews
Midland
28/06 – 03/07
SG$405/nighttotal: SG$2025 (5 )
7-11: Lake Beach Kayaks Fishing Swim: All Included
1 3
apartment , Tiny
This Tiny shoreline cottage boasts direct beach access and a private boat ramp, ideal for water sports enthusiasts. Sleeping eight comfortably in four bedrooms, this self-catering holiday home offers a fully equipped kitchen with dishwasher, central air conditioning, laundry facilities, a spacious deck with BBQ, and an on-site tennis court.
10 2 reviews
Midland
12/07 – 29/07
SG$411/nighttotal: SG$6987 (17 )
Georgian Bay Cottage/ Beach Access •Yard• Sleeps 8
1 2
apartment , Midland
This three-bedroom Tay cottage, a short walk from Patterson Park and Grandview beaches, offers easy access to Midland and Awenda Provincial Park (a short drive away). Sleeping eight comfortably across three bedrooms and a sofa bed, the property includes a kitchen with fridge and microwave, air conditioning, parking, high-speed Wi-Fi, Netflix, and a spacious yard ideal for barbecues; nearby attractions include the Waterfront Trail.
9.8 533 reviews
Midland
24/06 – 25/06
SG$178/nightfor 1 night
The Haunted House Apt 302
2 2
apartment , Midland
This charming flat is situated on the third floor of a historic Victorian house in Midland, just a short walk from the town museum and railway station. It has received excellent ratings for cleanliness, location, and overall experience, making it a great choice for travellers seeking a comfortable and convenient stay. The apartment is fully equipped with a kitchen, dining area, living room with Netflix, and two bedrooms with double beds, comfortably accommodating up to four guests. Amenities include air conditioning, parking, and self check-in, along with the unique features of a historic setting and a quiet atmosphere.
10 67 reviews
Midland
25/07 – 26/07
SG$229/nightfor 1 night
Sunset Loft
1 2
apartment , Midland
This one-bedroom apartment is located in a peaceful and central area of Midland, just a short walk from the marina, restaurants, and the Tay Trail. It has received excellent ratings for its cleanliness, location, and overall experience. The apartment offers a comfortable and convenient stay for two guests, with a fully equipped kitchen and a private backyard patio with a wood stove and BBQ. Guests can enjoy the Tay Trail, explore the nearby bush, or relax in the peaceful surroundings.
9.7 46 reviews
Midland
28/06 – 03/07
SG$219/nighttotal: SG$1095 (5 )
Georgian Bay Tiny Cabin - Bunkie Loft With A/c
1 2
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.
10 6 reviews
Midland
04/07 – 11/07
SG$347/nighttotal: SG$2429 (7 )
The Wright House - Modern 3bdrm Home In Midland!
3 5
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.
Midland
04/07 – 11/07
SG$341/nighttotal: SG$2387 (7 )
Chit Chat - Beach Lakefront Cabin On Georgian Bay
1 5
cabin , Tiny
Chit Chat is a modern lodge situated on Georgian Bay in Tiny, part of a family cottage compound offering a prime waterfront experience. This comfortable lodge accommodates eight guests with two bathrooms, features air conditioning, internet, and a kitchen, making it ideal for a relaxed cottage getaway.
9.3 57 reviews
Midland
03/09 – 20/12
SG$135/nighttotal: SG$14580 (108 )
Charming Cottage 2 Min From Private Beach
1 1
apartment , Midland
This charming cottage is situated in the peaceful town of Port McNicoll, just a short drive from Midland and a two-minute walk from a private beach. The property has received excellent ratings for its cleanliness, location, and overall experience. This three-bedroom holiday home comfortably accommodates six guests. The cottage boasts a fully-equipped kitchen, a relaxing porch, a private backyard perfect for outdoor gatherings, and access to a private beach with a playground and benches.
10 1 review
Midland
28/06 – 03/07
SG$302/nighttotal: SG$1510 (5 )
Cozy & Bright 3br Midland Home
1 3
apartment , Midland
This three-bedroom flat at 984 Wright Drive in Midland, Ontario, offers convenient access to the Georgian Bay area, situated only 500 meters from local attractions. This well-maintained property comfortably accommodates up to six guests, featuring a kitchen, air conditioning, and internet, making it suitable for families and small groups exploring Midland.
Best family friendly Midland holiday rentals
Among the 115 accommodations in Midland, here are the 4 best family friendly rentals
9.0 2 reviews
Midland
10/07 – 12/07
SG$534/nighttotal: SG$1068 (2 )
Beachfront Apt-patio/huge Beach!
2 2
apartment , Midland
This beachfront apartment in Penetanguishene, Ontario, is situated a short drive (approx. 8km) from Awenda Provincial Park and Rotary Park. The 50 square metre self-catering flat offers two bedrooms, one bathroom, sleeps five, and includes a fully equipped kitchen, private garden, terrace, Wi-Fi, and parking.
Midland
28/06 – 03/07
SG$624/nighttotal: SG$3120 (5 )
3 Bdrm | Bbq | Fire Pit - Steps To Waterfront Park
3 3
apartment , Midland
This Port McNicoll flat is located in a quiet residential area of Tay Township, a short walk from the 14-hectare Patterson Park waterfront and a brief drive to Midland's town centre shops and eateries. This 180 square metre residence accommodates up to six guests, offering three bedrooms, one bathroom, a fully equipped kitchen, a games room with a pool table and foosball, and a spacious private deck with a BBQ and fire pit, alongside convenient keyless entry and parking.
10 32 reviews
Midland
28/06 – 03/07
SG$352/nighttotal: SG$1760 (5 )
The Wright House - Modern 3bdrm Home In Midland!
1 3
apartment , Midland
This modern three-bedroom townhouse is situated in a quiet Midland neighbourhood, within walking distance of Georgian Bay General Hospital and local shops, and a short drive (approximately 8km) from Midland's town centre and attractions such as Marty's Shrine and St. Marie Among the Hurons. The self-catering property sleeps six guests, offering a newly renovated open-plan living space with modern amenities including stainless steel appliances, a Keurig coffee maker, and a Samsung Smart TV; it also includes a garage for bike storage and a 10% discount on Georgian Spirit Cruises is available.
Midland
28/06 – 03/07
SG$592/nighttotal: SG$2960 (5 )
Terrific Cottage At The Lakeside, Relax And Cozy.
3 2
cottage , Georgian Bay
This Georgian Bay holiday home is situated a short distance from Lake Huron, with Nicholson and Zumrud Islands less than 3.2km away. The 93 square metre property offers three bedrooms, two bathrooms, sleeps six, and includes a fully equipped kitchen, Jacuzzi, free Wi-Fi, and parking.
Best Midland holiday rentals with parking
10 2 reviews
Midland
10/07 – 12/07
SG$466/nighttotal: SG$932 (2 )
Balm Beach Tourist Cabin # 1
2 2
cottage , Tiny
This 2-bedroom holiday home in Tiny offers convenient access to Lake Huron and Georgian Bay, both within an 11-minute walk, providing car-free exploration opportunities. This rental sleeps four guests and features a fully equipped kitchen with a microwave, oven, and stove, alongside air conditioning and on-site parking.
9.2 142 reviews
Midland
28/06 – 03/07
SG$394/nighttotal: SG$1970 (5 )
Rawley Resort, Spa & Marina, Trademark Collection By Wyndham
1 3
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.
9.7 160 reviews
Midland
10/07 – 12/07
SG$421/nighttotal: SG$842 (2 )
Home On Bay
1 2
bungalow , Midland
This charming bungalow is conveniently situated just a short walk from the lake, grocery stores, an LCBO, a pharmacy, a pub, and a restaurant, making it a perfect base for exploring Midland. The property consistently receives excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay. The bungalow features four bedrooms, comfortably accommodating up to eight guests, making it ideal for families or groups of friends. The well-equipped kitchen, spacious garden, and air conditioning provide everything you need for a relaxing and enjoyable holiday, with additional features including a microwave, dishwasher, and parking.
9.4 3 reviews
Midland
10/07 – 12/07
SG$336/nighttotal: SG$672 (2 )
Cabin Peace And Cozy On Tay Trail Georgian Bay, Ski/snowboard/snowmobile/walks
1 2
cabin , Tay
This one-bedroom Tay cottage offers a peaceful retreat near Lake Huron and Georgian Bay, a short 0.8km walk from the lake and within 1.8km of Waubaushene Public Library and Waubaushene Beach Provincial Park. The 28 square metre self-catering property sleeps two guests and includes free Wi-Fi, a Smart TV, on-site parking, and a garden, with essential amenities provided.
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?
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 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.
Destinations nearby
Best Midland holiday rentals with a balcony
10 2 reviews
Midland
04/07 – 11/07
SG$467/nighttotal: SG$3269 (7 )
Cozy All-season Family Cottage In Balm Beach!
3 5
cottage , Tiny
This Tiny lakeside retreat is a short walk from Lake Huron and Georgian Bay, and within 3.2 kilometres of Jackson Beach Park and Cawaja Beach. Sleeping six guests, this three-bedroom cottage boasts a fully equipped kitchen (including fridge, microwave and stovetop), a fireplace, in-cottage laundry, a terrace, and air conditioning.
Midland
28/06 – 03/07
SG$697/nighttotal: SG$3485 (5 )
Spacious 4 Bdrm, Lake Views, Steps From The Beach
4 2
house , Tiny
This spacious 275 square metre detached house in Honey Harbour is situated 26 kilometres from the Tay River Basin and 25 kilometres from the Midland Cultural Centre. Ideal for families and groups of up to 15, this property offers direct beach access, stunning lake views from a balcony with outdoor furniture, a fully equipped kitchen, an outdoor fireplace and barbecue, children's play equipment, ski storage, and proximity to skiing, cycling, and hiking, with complimentary Wi-Fi and private parking.
9.2 5 reviews
Midland
28/06 – 03/07
SG$714/nighttotal: SG$3570 (5 )
Stunning Waterfront Cottage & Bunkie!
3 2
cottage , Midland
This Tay Township holiday home enjoys a beachfront location on Lake Huron and Georgian Bay, just under 5 km from Martyrs' Shrine. The 150-square-metre property sleeps six across three bedrooms and two bathrooms, offering a fully equipped kitchen, Wi-Fi, a spa, and a terrace overlooking the garden; housekeeping is available.
9.0 2 reviews
Midland
28/06 – 03/07
SG$596/nighttotal: SG$2980 (5 )
Balm Beach Bungalow - 3 Bedrooms
3 3
apartment , Tiny
This holiday cottage in Tiny offers direct access to Balm Beach and is situated just 10 minutes by car from Midland and Penetanguishene, placing you within easy reach of local restaurants, an arcade, shops, and Georgian Bay attractions such as St Marie Among the Hurons. This family-friendly apartment, spanning 55 square metres and accommodating up to six guests, features three bedrooms, one bathroom, a fully-equipped kitchen, air conditioning, high-speed WiFi, and outdoor amenities including a deck with a BBQ, fire pit, and balcony, alongside extensive beach gear for all-season enjoyment.
Best pet friendly Midland holiday rentals
Among the 115 accommodations in Midland, here are the 4 best pet friendly rentals
Midland
28/06 – 03/07
SG$284/nighttotal: SG$1420 (5 )
1bdrm Rental In Victoria Harbour
1 2
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.
10 94 reviews
Midland
12/07 – 29/07
SG$551/nighttotal: SG$9367 (17 )
Awenda Provincial Park Dream Cottage\n** Hot Tub & Dog Friendly **
2 2
cottage , Tiny
This three-bedroom cottage in Tiny is situated just 800 metres from Awenda Provincial Park and Lake Huron, with Georgian Bay a mere 160 metres away. The property boasts a fully equipped kitchen, a spa tub, laundry facilities, a games room, a garden, and barbecue grills, ensuring a comfortable and enjoyable stay for families and groups.
10 59 reviews
Midland
24/06 – 25/06
SG$214/nightfor 1 night
Hidden Gem
1 2
apartment , Midland
This recently renovated basement flat is situated in Midland's desirable West End, a 0.8 km walk from the Midland hospital and shops, and a 3.2 km drive from Midland's town centre, with Tiny Beaches 15 minutes away by car. This dog-friendly self-catering apartment sleeps two, boasting a fully equipped kitchen with Keurig and Nespresso machines, in-unit laundry, two smart TVs, private patio with BBQ, and access to two kayaks for exploring Georgian Bay; owners provide local recommendations for hiking, biking and beach locations.
Midland
03/09 – 20/12
SG$1092/nighttotal: SG$117936 (108 )
Forever Memories
1 1
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.