Holiday Rentals in Midland

115 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 115 accommodations in Midland, here are the 4 best family friendly rentals

Beachfront Apt-patio/huge Beach! - Midland
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.
3 Bdrm | Bbq | Fire Pit - Steps To Waterfront Park - Midland
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.
The Wright House - Modern 3bdrm Home In Midland! - Midland
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.
Terrific Cottage At The Lakeside, Relax And Cozy. - Midland
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

Balm Beach Tourist Cabin # 1 - Midland
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.
Rawley Resort, Spa & Marina, Trademark Collection By Wyndham - Midland
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.
Home On Bay - Midland
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.
Cabin Peace And Cozy On Tay Trail Georgian Bay, Ski/snowboard/snowmobile/walks - Midland
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?

    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.

Destinations nearby

Best Midland holiday rentals with a balcony

Cozy All-season Family Cottage In Balm Beach! - Midland
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.
Spacious 4 Bdrm, Lake Views, Steps From The Beach - Midland
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.
Stunning Waterfront Cottage & Bunkie! - Midland
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.
Balm Beach Bungalow - 3 Bedrooms - Midland
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

1bdrm Rental In Victoria Harbour - Midland
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.
Awenda Provincial Park Dream Cottage\n** Hot Tub & Dog Friendly ** - Midland
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.
Hidden Gem - Midland
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.
Forever Memories - Midland
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.
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