Holiday houses in Midland

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Midland

Guests agree: these stays are highly rated for location, cleanliness and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Apartment in Penetanguishene

4.88 out of 5 average rating, 377 reviews

The Haunted House Apt 302

As you pull into the driveway this 1885 Victorian towers above you, your mouth drops in awe of the size. Up the porch to enter a small front door, a dimly lit winding staircase creaks as you ascend to 3rd floor. Original architecture painted many times over oozes with history. 70 years ago the house was turned into apartments, unloved for many of those years, time has definately taken its tole, yet to the spirits within, their big old house still stands proud and distinguished in all its glory.

21–28 Jan

$239 NZD per night

Guest favourite

Apartment in Penetanguishene

4.92 out of 5 average rating, 120 reviews

Church Hill Haven Bed & Breakfast Guest Suite #1

A continental breakfast (a fruit, yogurt & baked good) now available for a small extra cost - please give at least 48 hours if you would like this, (need to know allergies & preferences.) or save money & bring your own & prepare in equipped kitchen. Separate basement walkout entrance with own back deck. (The owner lives on the upper level.) There is a queen size bed in the bedroom & a pull-out queen bed in the LR. The toilet & sink are separate from the walk-in shower. BBQ available in summer.

7–14 Aug

$138 NZD per night

Guest favourite

Place to stay in Wasaga Beach

5.0 out of 5 average rating, 190 reviews

Newly Built Woodsy Loft Retreat

Welcome to Woodsy Loft, a newly built retreat. A great spot for a getaway! A perfect home base for not just the beach and stunning walks into the sunset, but Blue Mtn, Scandinavian Spa, Collingwood, Cross Country Skiing Provincial Park and a brand new casino, all close by. Packed with amenities like screened in patio, XL bathtub, King size bed, 'The Frame' Smart TV, full kitchen, fast WIFI, motorized blind...and the list goes on. Situated and designed to offer max. privacy and relaxation.

16–23 Sep

$281 NZD per night

Guest favourite

Apartment in Midland

4.95 out of 5 average rating, 22 reviews

Loft By The Bay

Welcome to our charming second storey apartment in downtown Midland, Ontario. This cozy space features a bedroom, office with futon, full kitchen, bathroom, laundry, and a bright open concept living area. Enjoy easy access to local shops, restaurants, and attractions. Explore the picturesque waterfront and nearby hiking trails. Retreat to this comfortable and inviting apartment after a day of work or play. Book your stay today for a convenient, comfortable, and memorable experience in Midland.

5–12 Nov

$138 NZD per night

Guest favourite

Home in Penetanguishene

4.97 out of 5 average rating, 143 reviews

White Rolling Sands of Penetanguishene by theatre

Enjoy a firepit in the private backyard of a large deep lot backing onto woods with trails. Local walking and cycling routes, or stay home and enjoy the veggie and flower gardens from back deck. Fully licensed and located close to Kings' Wharf Theatre / Discovery Harbour. Experience the natural beauty of Tiny Beaches, Georgian Bay Islands N.P and Awenda P.P. nearby (Park pass available for use). Marinas, beaches, boat cruise of the islands, Ste Marie Among the Hurons and Wye Marsh are nearby.

21–28 Apr

$210 NZD per night

Guest favourite

Loft in Midland

4.88 out of 5 average rating, 285 reviews

Nest By The Bay - Downtown Midland / Private Loft

Luxury, Comfort & Style. This one-of-a-kind rental, "Nest By The Bay", is located in Downtown Midland. Walk everywhere, park your car & enjoy what Midland has to offer. Midland Harbour is only minutes by foot. Live our lifestyle, enjoy our many festivals, professional theatre, artisans, culinary cuisine, seasonal events & so much more! See our other listing "Perch By The Bay", also at this same location. 2 nights min. preferred, 1 night by request. Listing not suitable for ages under 6.

31 Dec – 7 Jan

$243 NZD per night

Guest favourite

Farm stay in Gravenhurst

4.98 out of 5 average rating, 369 reviews

Stix N Stones (Includes Light Breakfast & Kayaks)

Nestled in the woods on Walkers Point, this is a great opportunity to reconnect with nature. We promise when you leave you’ll appreciate the forest as much as the water that surrounds us. Although we are not on the water, we are a 3min drive to a semi-private beach. Kayaks & life vests included (& delivered). Snowshoes incl in winter. Light breakfast is yogurt & fruit. Short distance to renowned hiking trails, Hardy Lake Park, Sawdust City & Clearlake Brewery, Muskoka Winery.

28 Dec – 4 Jan

$215 NZD per night

Guest favourite

Cottage in Port McNicoll

4.98 out of 5 average rating, 123 reviews

Boe's Cottage: Newly Renovated - Great WIFI

Experience Southern Georgian Bay - Ontario's Four Season Playground. Just 90 Minutes from Toronto! Relax in our fully renovated 4 season cabin with all the amenities of home. Steps from the lake with parks, beaches, hiking, kayaking. And in the winter, snowshoe, skate, snowmobile, cross country & downhill skiing at Mount st. louis moonstone Great setup for a 'working' vacation with excellent WIFI 10 Minutes to Midland for restaurants & unique shopping experiences

21–28 Sep

$238 NZD per night

Guest favourite

Guesthouse in Victoria Harbour

4.98 out of 5 average rating, 228 reviews

Sunset Beach Cottage

Part log treehouse, part beach house and 100% of what you need to enjoy a peaceful getaway only 1.5 hours from Toronto! Walk up the private staircase and pause to enjoy the spectacular treetop and waterfront views from your own wraparound deck before entering your 900 sq. ft. oasis. Enjoy access to your own lawn, picnic table and beach* area and all that Georgian Bay and the area has to offer. *water levels fluctuate Insta: sunset_beach_cottage_canada

3–10 Oct

$349 NZD per night

Guest favourite

Cottage in Torrance

4.97 out of 5 average rating, 193 reviews

Beautiful Nine Mile Lake

Beautiful Muskoka getaway! Newly renovated 4 season waterfront cottage! Stunning views! Located on picturesque Nine Mile Lake. Over 70% of the lake is crown land. Perfect for kayaking and canoeing to enjoy all the beauty Muskoka is known for. We have kayaks a canoe and a paddle board for you to enjoy. Plenty of sun exposure on the dock you can swim all day long. Close to hiking and snowmobile trails. May 15-Oct 2 Minimum 6 nights with a Sunday check in.

5–10 May

$288 NZD per night

Guest favourite

Cottage in Tiny

4.94 out of 5 average rating, 203 reviews

Bluestone

Bluestone is located less than 10 minutes' drive from beautiful Awenda Provincial Park in Tiny, Ontario. Every choice was made with guest comfort in mind. In the Summertime, take a short walk down a wooded path to Georgian Bay and perfect swimming, or explore a hiking trail and take in the natural beauty of the area. In Winter, enjoy skiing and snowshoeing locally, or stay in, put a record on, and cozy up by the fire. License #STRTT-2024-017

20–27 Dec

$319 NZD per night

Superhost

Cottage in Port Severn

4.86 out of 5 average rating, 130 reviews

Cottage "Down By The Bay"

1 bdrm cottage in beautiful Port Severn, ON with firepit, WIFI, Heat and AC. Great location year round. Located on the main road into Honey Harbour, ON and close to amenities such as Tim Hortens, LCBO, gas stations and restaurants. Near water and beaches (NOT A WATERFRONT- Port Severn Park and Beach is 7 min drive) Right beside entrance to OFSC trails for snowmobiling Mount ST. Louis is a 20 min drive Fishing/ice fishing options nearby

19–26 Nov

$157 NZD per night