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

Luxury 4br Lakefront Cottage W/ Sauna & Dock! - Midland
Midland
12/09 – 21/09
SG$759/nighttotal: SG$6831 (9 )

Luxury 4br Lakefront Cottage W/ Sauna & Dock!

4 2
cottage , Midland
This waterfront holiday home in Tay offers direct access to shallow waters via a private dock and is located approximately 1.6 to 2.4 kilometres from the Huronia Museum and Ste-Marie among the Hurons.
This spacious 230 square metre lodge comfortably accommodates up to 10 guests across four bedrooms, featuring a modern kitchen with a wine fridge, a gas fireplace, a wood-burning barrel sauna, kayaks, and parking for seven vehicles.
Discounted Rates. Farm + Atv Trails + Fire Pit - Midland
9.0 2 reviews
Midland
27/06 – 04/07
SG$358/nighttotal: SG$2506 (7 )

Discounted Rates. Farm + Atv Trails + Fire Pit

1 2
apartment , Tay
This cabin is located in Tay, just five minutes from a major shopping centre and surrounded by forest, gardens, and fruit trees. It has excellent user, location and cleanliness ratings, making it a great choice for travellers.
The property spans seven acres and can accommodate up to ten guests. It features a fully equipped kitchen, a private trampoline and soccer field, a fire pit, a BBQ, and access to nearby bike, ATV, and snowmobile trails.
Rawley Resort, Spa & Marina, Trademark Collection By Wyndham - Midland
9.2 142 reviews
Midland
12/09 – 21/09
SG$395/nighttotal: SG$3555 (9 )

Rawley Resort, Spa & Marina, Trademark Collection By Wyndham

1 2
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.
Pickerel Point - Midland
Midland
26/06 – 27/06
SG$382/nightfor 1 night

Pickerel Point

2 2
house , Georgian Bay
This detached house, situated in Port Severn, is located 37 kilometres from Tay River Basin and Midland Cultural Centre, offering a gateway to the Georgian Bay region.
This pet-friendly, family-oriented cottage spans 79 square metres with two bedrooms and one bathroom, accommodating up to seven guests with amenities including free WiFi, private parking, a garden, balcony, and a terrace with lake views.

Best Midland holiday rentals with parking

2 Bdrm Waterfront Retreat - Huge Beach! - Midland
10 1 review
Midland
12/09 – 21/09
SG$316/nighttotal: SG$2844 (9 )

2 Bdrm Waterfront Retreat - Huge Beach!

3 2
apartment , Penetanguishene
This family-friendly apartment in Penetanguishene is conveniently located just 3km from Awenda Provincial Park and 2.4km from the Copeland Creek Wetlands Trail, offering easy access to outdoor activities.
The 50 square metre self-catering property sleeps five guests across three bedrooms and one bathroom, and boasts a well-equipped kitchen, free Wi-Fi, air conditioning, on-site amenities including a garden, tennis court and spa, plus parking.
Terrific Cottage At The Lakeside, Relax And Cozy. - Midland
Midland
28/06 – 03/07
SG$583/nighttotal: SG$2915 (5 )

Terrific Cottage At The Lakeside, Relax And Cozy.

3 3
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.
3 Bedroom Waterfront Oasis / Water Toys! - Midland
Midland
12/09 – 21/09
SG$427/nighttotal: SG$3843 (9 )

3 Bedroom Waterfront Oasis / Water Toys!

4 2
apartment , Midland
This beachfront flat in Penetanguishene, a short 8km drive from both Awenda Provincial Park and Penetanguishene Rotary Park, offers easy access to Midland attractions.
The 90 square metre property sleeps eight guests in four bedrooms, one bathroom, and boasts a fully equipped kitchen, private garden, spa, parking, and free Wi-Fi.
Lakeside Retreat: Steps To Beach - Midland
9.4 3 reviews
Midland
12/09 – 21/09
SG$463/nighttotal: SG$4167 (9 )

Lakeside Retreat: Steps To Beach

3 2
cabin , Midland
This charming cottage is located in Tay Township, just a short 15-minute drive from Midland, offering easy access to local attractions like the Huronia Museum and Sainte-Marie among the Hurons. The surrounding area provides a peaceful retreat, perfect for families and couples seeking a relaxing escape.
The Hilde House is a spacious 83 square metre property with three bedrooms and one bathroom, comfortably accommodating up to five guests. The cottage features a fully equipped kitchen, a private beach, a cosy fireplace, and a children's playground, ensuring a comfortable and enjoyable stay for all.

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

Modern 4br Cottage, Hot Tub & Sauna On Tay Trail - Midland
9.4 235 reviews
Midland
12/09 – 21/09
SG$519/nighttotal: SG$4671 (9 )

Modern 4br Cottage, Hot Tub & Sauna On Tay Trail

4 2
house , Tay
This four-bedroom house is located in Waubaushene, just 19 kilometres from Orillia Community Centre Arena and 12 kilometres from Midland Cultural Centre. The area offers a peaceful setting with easy access to Georgian Bay, trails, and nearby attractions. This property has received excellent user ratings for location, cleanliness, and overall experience.
This spacious 111 square metre property comfortably accommodates up to eight guests. The house is equipped with modern amenities including a fully equipped kitchen, a fireplace, a hot tub, a sauna, a tennis court, and a private garden, making it ideal for families and groups seeking a relaxing and enjoyable stay.
4br Honey Harbour Cottage | Hot Tub & Fire Pit - Midland
9.6 143 reviews
Midland
28/06 – 03/07
SG$415/nighttotal: SG$2075 (5 )

4br Honey Harbour Cottage | Hot Tub & Fire Pit

4 3
house , Georgian Bay
This charming holiday home is located in Honey Harbour, a picturesque village on the shores of Georgian Bay, just 24 miles from the Tay River Basin and 35 miles from Lake Simcoe Regional Airport. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The house has four bedrooms, comfortably accommodating up to eight guests, with a total floor area of 111 square metres. Guests can enjoy a fully equipped kitchen, a relaxing garden, a hot tub, and a terrace, as well as free Wi-Fi, private parking, and access to a range of outdoor activities in the surrounding area.
Sandy Beach/boating/swimming/hot Tub/marina/trails - Midland
8.8 50 reviews
Midland
03/09 – 20/12
SG$487/nighttotal: SG$52596 (108 )

Sandy Beach/boating/swimming/hot Tub/marina/trails

3 2
cottage , 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.
Farm House - Midland
8.5 13 reviews
Midland
12/09 – 21/09
SG$809/nighttotal: SG$7281 (9 )

Farm House

1 2
house , Oro-Medonte
This farmhouse is situated in Oro-Medonte, 21km from the Tay River basin, 21km from the Midland Cultural Centre, and 28km from the Orillia Community Centre, offering a peaceful rural setting. The property has received very good user ratings and excellent ratings for location and cleanliness.
This 186 square metre house can accommodate up to 25 guests and features a comfortable bedroom, a fully equipped kitchen, a garden, a terrace, and free parking. Guests can enjoy a cozy fireplace, prepare their own meals, and relax in the peaceful surroundings.

Best pet friendly Midland holiday rentals

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

Georgian Bay Retreat - Apartment In Midland - Midland
9.7 64 reviews
Midland
12/09 – 21/09
SG$153/nighttotal: SG$1377 (9 )

Georgian Bay Retreat - Apartment In Midland

1 2
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.
Your Happy Place - Midland
9.8 9 reviews
Midland
27/06 – 04/07
SG$270/nighttotal: SG$1890 (7 )

Your Happy Place

4 2
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.
Cozy Cottage 20 Min From Ski Resorts - Midland
9.0 26 reviews
Midland
28/06 – 03/07
SG$902/nighttotal: SG$4510 (5 )

Cozy Cottage 20 Min From Ski Resorts

3 3
cottage , Severn
This family-friendly cottage is located just 500 metres from the waterfront of Lake Huron and Georgian Bay, a short 15-minute drive from Waubaushene Beaches Provincial Park and the Matchedash Bay Trail Trailhead. It has received excellent ratings for its cleanliness, location and user experience.
This 93 square metre property has three bedrooms and one bathroom, comfortably sleeping up to 12 guests. It offers a private outdoor pool, a spa tub, an arcade/game room, a garden, barbecue grills, free Wi-Fi, and a fully equipped kitchen.
Beachfront Apt-patio/huge Beach! - Midland
9.0 2 reviews
Midland
12/09 – 21/09
SG$316/nighttotal: SG$2844 (9 )

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.
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