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

Find Holiday Rentals in the City Centre of Midland

Reconnect deeply with your significant other at peaceful holiday rentals for couples in Midland, offering romantic, quiet settings.

The Midland Nest | Cozy 2br Walkout Suite - Midland
9.7 7 reviews

The Midland Nest | Cozy 2br Walkout Suite

apartment, Midland
This centrally located flat in Midland offers convenient access to downtown, the harbour, and numerous restaurants and attractions, with a private walkout leading to a large, tree-lined garden and patio.
This spacious lower unit features an open-concept living and dining area, a sunroom with ample natural light, and accommodates up to three guests with a king bed in the primary bedroom and a single bed in the second, providing essential amenities for a comfortable stay.
Downtown Luxury Loft With Rooftop Terrace - Midland
10 11 reviews

Downtown Luxury Loft With Rooftop Terrace

apartment, Midland
This stylish loft apartment is located in downtown Midland, just a few steps from the waterfront, harbourfront trails, restaurants, and shops.
This 111.5 square meter loft sleeps four guests across two Queen beds and features a fully equipped kitchen, in-suite laundry, high-speed Wi-Fi, and a private rooftop terrace with Midland Bay views, a gazebo, sky bar, and BBQ.
The Wright House - Modern 3bdrm Home In Midland! - Midland
10 37 reviews

The Wright House - Modern 3bdrm Home In Midland!

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.
Close To Hospital And School 4 Bedroom Bungalow - Midland
9.7 85 reviews

Close To Hospital And School 4 Bedroom Bungalow

apartment, Midland
This apartment is located in Midland, a short walk from Aberdeen Boulevard and within easy reach of Balm Beach, Little Lake, and the Sainte-Marie among the Hurons museum. It has consistently received excellent ratings for user experience, location, and cleanliness.
This spacious home sleeps up to 8 guests and offers 4 bedrooms and 2 bathrooms. The apartment features a private backyard with ravine views, a large basement for group activities, an outdoor deck with BBQ, and a master bedroom with deck access.

Best Midland holiday rentals with air conditioning

The Discovery Retreat: Heated Pool, Hot Tub, Firepit, Bbq, Sauna, Game Room - Midland
No reviews

The Discovery Retreat: Heated Pool, Hot Tub, Firepit, Bbq, Sauna, Game Room

apartment, Midland
This six-bedroom, four-bathroom property is located in Penetanguishene, approximately 240km from Toronto and near Discovery Harbour and the Midland Golf and Country Club.
Sleeping up to 18 guests, this spacious holiday home boasts a heated 56m² pool, hot tub, games room with pool table, and is equipped with high-speed internet and an EV charger.
Victoria Harbour Cottages - Midland
9.3 29 reviews

Victoria Harbour Cottages

house, Midland
Victoria Harbour Cottages are located on the beachfront in Victoria Harbour, just 5.5 miles from Tay River Basin and 29 miles from Lake Simcoe Regional Airport. The cottages have received excellent ratings for location, cleanliness, and overall experience.
These one-bedroom cottages offer a comfortable and convenient stay for travellers. Enjoy the on-site amenities, including a fully equipped kitchen, private balconies, and access to free bikes for exploring the beautiful surroundings.
Lakefront Retreat- Private Beach, Up To 30 Guests! - Midland
10 9 reviews

Lakefront Retreat- Private Beach, Up To 30 Guests!

apartment, Midland
Rolling Sands Retreat, a five-unit property on Georgian Bay's shoreline, is situated a short drive from Midland, offering easy access to Balm Beach (24km), Awenda Provincial Park (42km), and Wasaga Beach (53km).
This large holiday home sleeps up to 31 guests across five units, each with a fully equipped kitchen, private entrance, BBQ, and firepit; enjoy 82 metres of private beach, water toys, and a 10% discount on boat rentals at a nearby marina.
Georgian Bay Cottage/ Beach Access Yard Sleeps 8 - Midland
10 6 reviews

Georgian Bay Cottage/ Beach Access Yard Sleeps 8

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.

Frequently asked questions about holiday rentals in Midland

  • What are the top family-friendly attractions in Midland?

    The Midland Bay Marina is a popular spot for families, with its playground, splash pad, and boat tours. The Huronia Museum is another great option, with interactive exhibits and hands-on activities for kids. Don't forget to check out the Midland Public Library, which has a fantastic children's section.
  • What are the best Airbnb and holiday rentals in Midland?

  • When is the best time to book a vacation rental in Midland?

    The peak season for tourism in Midland runs from June to August, so it's best to book your vacation rental early if you're planning to visit during those months. You'll find more availability and potentially lower prices if you travel in the shoulder seasons of spring or autumn.
  • 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 lively event with live music, food vendors, and family-friendly activities. If you're interested in arts and culture, the Midland Cultural Centre hosts a variety of performances and exhibitions throughout the year. For a unique experience, check out the annual Midland Bay Regatta in August, a celebration of sailing and maritime heritage.
  • What are the best holiday rentals with a pool in Midland?

  • What are the best budget-friendly activities in Midland?

    Take a walk or bike ride along the scenic waterfront trail. Enjoy a picnic at one of Midland's many parks, like Little Lake Park or King's Orchard Park. Visit the free exhibits at the Huronia Museum or the Midland Public Library.
  • What are the best rentals for families and kids in Midland?

  • What are the best restaurants with local dishes in Midland?

    For fresh seafood, check out The Docks Restaurant, located right on the waterfront. If you're in the mood for something more casual, try the popular local spot, The Midland Tap House, known for its burgers and craft beers. For a taste of Italian cuisine, head to La Piazza Ristorante.
  • 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 popular choice for both walking and cycling, offering scenic views of Georgian Bay. For a more challenging ride, try the 10 km loop around Little Lake. The Midland Trailway is a paved trail that runs through the town, perfect for a leisurely stroll or bike ride.
  • Are there pet-friendly attractions in Midland?

    Many of Midland's parks and beaches are dog-friendly, including Little Lake Park and the waterfront trail. The Huronia Museum also welcomes well-behaved dogs on a leash. Check with individual businesses and attractions to confirm their pet policies.
  • What are the benefits of choosing a vacation rental in Midland?

    Vacation rentals often offer more space and privacy compared to hotels. They can also be a more affordable option, especially for families or groups travelling together. Many rentals are located in desirable neighbourhoods, giving you a more authentic local experience.
  • What are the top sports attractions and facilities in Midland?

    Midland is home to the Midland Midgets, a junior hockey team that plays in the Ontario Hockey Association. The town also has a number of recreational facilities, including the Midland Community Centre, which offers a variety of programs and activities, including swimming, fitness classes, and ice skating.

Popular destinations

Choose the Right Holiday Rentals with a Balcony in Midland

Private balconies with city skyline views come as standard at these holiday rentals in Midland for a lovely start to your day.

Stunning Waterfront Cottage & Bunkie! - Midland
9.4 6 reviews

Stunning Waterfront Cottage & Bunkie!

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.
Lakefront Retreat- Private Beach, Up To 30 Guests! - Midland
No reviews

Lakefront Retreat- Private Beach, Up To 30 Guests!

cottage, Midland
This waterfront five-plex, located in Penetanguishene, is a short 5-10 kilometre drive from Midland, offering convenient access to Awenda Provincial Park and local attractions such as the Midland Cultural Centre and Ste-Marie among the Hurons.
This spacious property boasts 270 feet of private Georgian Bay shoreline, accommodating up to 31 guests with 14 bedrooms and 5 bathrooms spread across 250 square metres, featuring modern interiors, private barbecues, firepits, and a variety of water toys for an ideal retreat.
Sandy Beach/boating/swimming/hot Tub/marina/trails - Midland
8.8 56 reviews

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

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.
Pickerel Point - Midland
9.0 5 reviews

Pickerel Point

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.

Popular Family-Friendly Holiday Rentals in Midland

Choosing a holiday rental built for families in Midland means city attractions are close by for a much smoother trip.

Welcoming Waterfront Cottage - Midland
9.9 32 reviews

Welcoming Waterfront Cottage

apartment, Midland
This waterfront apartment is just a short drive from Midland, offering easy access to the Georgian Bay and its surrounding attractions, and is located in a peaceful and quiet community. The apartment boasts excellent ratings for location, cleanliness, and user experience.
The apartment is spacious and comfortable, perfect for families or groups of up to six guests. Enjoy private beach access, a dock for swimming, kayaking, or fishing, a full kitchen, an outdoor grill, and an enclosed backyard for children to play.
Cozy Beachside Getaway  Steps From Balm Beach! - Midland
10 2 reviews

Cozy Beachside Getaway Steps From Balm Beach!

cottage, Tiny
This holiday home is located in Tiny, mere steps from Balm Beach and within a 10-minute drive of Midland and Penetanguishene.
This 27-square-metre lodge accommodates four guests across two bedrooms and one bathroom, featuring a fully equipped kitchen, air conditioning, WiFi, a garden with a fire pit and BBQ, a sunroom with lake views, and a 10% discount offer on a Georgian Spirit Cruise from Midland.
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.
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.

Handpicked Self-Catering Rentals with Parking in Midland

On-site parking takes one thing off your list when visiting Midland. Our holiday rentals have it included.

Spacious -Custom Build Lakehouse-strtt-2026-127 - Midland
9.4 10 reviews

Spacious -Custom Build Lakehouse-strtt-2026-127

cottage, Tiny
Gleaming Family Friendly Vacation Home Near Beach - Midland
9.9 35 reviews

Gleaming Family Friendly Vacation Home Near Beach

apartment, Midland
3 Bedroom Waterfront Oasis / Water Toys! - Midland
9.8 25 reviews

3 Bedroom Waterfront Oasis / Water Toys!

house, Midland
The Little Lake House-cozy 2bdrm - Midland
8.0 4 reviews

The Little Lake House-cozy 2bdrm

apartment, Midland

Compare Luxury Holiday Rentals in Midland

Comfort, quality, and a prime location - each luxury holiday rental or Airbnb in Midland is selected with these standards in mind. Pick your favourite today.

The Wright House - Modern 3bdrm Home In Midland! - Midland
10 8 reviews

The Wright House - Modern 3bdrm Home In Midland!

apartment, Midland

Explore Pet-Friendly Holiday Rentals in Midland

Bringing your dog to Midland? These holiday rentals are perfectly set up with dog parks nearby and city walks on the doorstep.

Georgian Bay Cottage - Midland
No reviews

Georgian Bay Cottage

apartment, Midland
Welcome To Waterfront Paradise On Georgian Bay - Midland
9.9 60 reviews

Welcome To Waterfront Paradise On Georgian Bay

apartment
Beachfront Apt-patio/huge Beach! - Midland
9.0 2 reviews

Beachfront Apt-patio/huge Beach!

apartment, Midland
2 Bdrm Waterfront Retreat - Huge Beach! - Midland
10 1 review

2 Bdrm Waterfront Retreat - Huge Beach!

apartment, Midland

Find the Best Holiday Rentals with a Pool in Midland

These holiday rentals and Airbnbs in Midland include a pool, so a proper swim in the heart of the city is always on the cards.

Float Cabin On Georgian Bay 4 - Midland
No reviews

Float Cabin On Georgian Bay 4

barge
Float Cabin On Georgian Bay 2 - Midland
No reviews

Float Cabin On Georgian Bay 2

barge
Float Cabin On Georgian Bay 3 - Midland
No reviews

Float Cabin On Georgian Bay 3

barge
Georgian Bay Oasis: Pool, Hot Tub, Beach & Trails - Midland
No reviews

Georgian Bay Oasis: Pool, Hot Tub, Beach & Trails

apartment, Midland

Check Out Holiday Rentals with a Hot Tub in Midland

Whether you prefer a jacuzzi or a hot tub, these holiday rentals in Midland include one for your private use. See what catches your eye now.

Perfect Summer Gateway.lots To Do Here - Midland
9.7 69 reviews

Perfect Summer Gateway.lots To Do Here

apartment, Midland
Impressive Modern Waterfront Home On Georgian Bay - Midland
6.0 1 review

Impressive Modern Waterfront Home On Georgian Bay

house, Midland
Awenda Provincial Park Dream Cottage ** Hot Tub & Dog Friendly ** - Midland
10 95 reviews

Awenda Provincial Park Dream Cottage ** Hot Tub & Dog Friendly **

cottage, Tiny
4br Honey Harbour Cottage | Hot Tub & Fire Pit - Midland
9.5 152 reviews

4br Honey Harbour Cottage | Hot Tub & Fire Pit

house, Georgian Bay
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