House holiday rentals in Midland

Find and book unique houses on Airbnb

Top-rated house rentals in Midland

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

0 of 0 items showing

1 of 3 pages

Guest favourite

Home in Port McNicoll

4.92 out of 5 average rating, 13 reviews

Paradise Point Steps from Georgian Bay Great WIFI

Welcome to the Paradise Point Cottage. From the moment you walk in you'll feel your stress melt away. The original wood workmanship has been maintained to preserve the cabin escape feeling. Watch the 75" smart TV or play games by the stone fireplace. Enjoy cooking in the large dine-in kitchen, a place perfect for creating memories. On a half-acre, this property has a view of the waterfront from the front & back, easy access to Georgian Bay, and snowmobiling from the front door. Don't miss out!

30 Aug – 6 Sep

$269 SGD per night

Guest favourite

Home in Penetanguishene

4.98 out of 5 average rating, 150 reviews

Lafontaine Beach Paradise

Welcome to our Retreat in Paradise! A place where your body, mind and soul will relax! This stately executive home offers an elegant appeal inside and out, with 4000 sf of living space boasting an impressive interior with high-end finishes. Perfectly located close to the beach, trails and all amenities. Large windows and surrounded by mature trees on a beautiful quiet street. This home is ready for you to enjoy your get away. Time to start building your loving family memories! READ HOUSE RULES!

4–11 Jun

$535 SGD per night

Guest favourite

Home in Midland

4.89 out of 5 average rating, 57 reviews

4-bdr bungalow with walkout bsm & 2 private decks

Relax with the whole family or friends at this peaceful location with a private backyard facing a mature ravine. Rent Skiis/Snowboards at Mt.St. Louis and hit the slopes in the winter. Maybe bring your gear and try Ice Fishing in the Georgean Bay. Visit in the summer and enjoy a walk along the Aberdeen Boulevard, catch a tan at the sandy Balm Beach or at the Little Lake! Be sure to visit the 'Sainte-Marie among the Hurons' museum and immerse yourself into the lives of early European settlers.

28 May – 4 Jun

$213 SGD per night

Guest favourite

Home in Penetanguishene

4.97 out of 5 average rating, 143 reviews

White Rolling Sands of Penetang 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.

19–26 May

$159 SGD per night

Guest favourite

Home in Midland

5.0 out of 5 average rating, 42 reviews

Historic Coach House hosted by John & Donna

Approx. 600 sq ft of living space. 2 guests. 1 large bedroom with queen canopy bed - includes linens. 1 bath with original claw tub and shower - includes soap, toilet paper, towels. Great location on historic street. Kitchen - fridge, stove, dishwasher, coffee maker, toaster Dining room with antique table and chairs. Sitting room. Free parking for 1 car on premises. Air conditioning and heating. Wi-Fi. Private entrance. Large deck. Minimum stay 2 nights. Please no pets. No smoking or vaping.

2–9 Jul

$169 SGD per night

Guest favourite

Home in Bracebridge

4.93 out of 5 average rating, 341 reviews

Muskoka Hideaway-hot tub/private trails/wood stove

Hidden amongst the trees in the middle of Muskoka, this Hemlock log cabin boasts high ceilings and a true "cabin in the woods" feel. Its not hard to relax and unwind with a coffee in front of the fire, or go and explore along the private forest trails (1-2k of walking trails). As well, downtown Bracebridge is a convenient 10 minute drive away with all amenities. There is a veggie garden on the property and depending when you come you can pick away at it :) Pets are welcome in the home!

29 May – 5 Jun

$324 SGD per night

Superhost

Home in Orillia

4.85 out of 5 average rating, 203 reviews

Waterfront Cottage Over-the-Water view w fast Wifi

Our cottage backs directly onto lake Simcoe with a view overlooking the water reminiscent of a four season water villa bungalow. Enjoy the entire house with your family and friends and be captivated by nature's beauty as the sun sets behind the treeline across the lake. Easy access to lake Couchiching for fishing in the summer and ice fishing in the winter, 30 mins to Mount St. Louis for skiing and snowboarding, 30 mins to Vetta Nordic Spa and Casino Rama is only a 10 minute drive away!

24 Nov – 1 Dec

$262 SGD per night

Guest favourite

Home in Tiny

4.86 out of 5 average rating, 110 reviews

Beachy Blue Bay Cottage - licence #STRTT-2024-195

A 2 min walk to the beach, this 4 bedroom Cottage with Circular Driveway is bright and newly renovated with an open concept main floor. Very private and surrounded by mature trees. Relax on a very large deck with gas BBQ, seating and patio table. Over looking the deck is the fire pit area with lots of room for the kids to play & roast s’mores. The basement is well equipped with pool table, dart board, air-hockey, kids toys, board games & a small TV with lots of movies to snuggle up to!

16–23 Oct

$457 SGD per night

Superhost

Home in Midland

4.85 out of 5 average rating, 40 reviews

Outdoor Haven - Barrel Sauna - Skiing & Fishing

Bring your group to this cheerful country home with modern updates (in progress). Close to Georgian Bay, you are a 10-minute walk to the waterfront or downtown core. With a large backyard, fire pit, Sauna and bbq you have the option to enjoy the backyard or spend your time inside. Cedar ceilings throughout the main floor and an electric fireplace to provide a cozy, cottage vibe in the town of Midland. Ten minutes to the water close for fishing and 30 minutes from the closest ski hill.

15–22 Apr

$177 SGD per night

Guest favourite

Home in Victoria Harbour

4.83 out of 5 average rating, 134 reviews

Georgian Bay Paradise

Enjoy a relaxing vacation away from the hustle & bustle in this delightful 3 bedroom waterfront cottage. Just 90 minutes north of Toronto, this newly-renovated, gorgeous retreat is right on Georgian Bay, one of the world's most sought after destinations. Revel in breathtaking views, amazing sunsets and the privacy of numerous cedars. You will love the sun, sand, rock and waves which will captivate you. Access your own deck, lawn, and beach as well as many fun winter activities.

29 Oct – 5 Nov

$193 SGD per night

Guest favourite

Home in Gravenhurst

4.9 out of 5 average rating, 341 reviews

*Muskoka Bay Resort* All Season Modern Loft 3 Beds

Welcome to Lida's Home @ Muskoka Bay Resort - now with newly upgraded kitchen and all new appliances for even better stays! Near Muskoka Wharf and downtown Gravenhurst for easy access. Come and enjoy the modern luxury and gorgeous scenic views of Muskoka, there is something for everyone!! The golf course was rated top 10 in Canada and #74 on golf.com for 2021-2022 of over 18,000 courses, and it offers the best of Muskoka in all seasons.

3–10 Sep

$329 SGD per night

Guest favourite

Home in Midland

4.83 out of 5 average rating, 169 reviews

The Little Lake House

The Little Lake House can be described as charming, and cozy. Located close to downtown, and a short walk from Little Lake Park, this newly renovated house is a sweet spot for your next stay in Midland. Relax, and read a book in the little backyard. Go out for a scrumptious meal downtown, or choose to stay in, and cook in our airy & bright kitchen. With 2 cozy bedrooms, you'll feel well rested in one of our pillow-top beds.

28 Feb – 7 Mar

$158 SGD per night