Family-friendly holiday rentals in Midland

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Top-rated family-friendly rentals in Midland

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Guest house in Orangeville

4.95 out of 5 average rating, 310 reviews

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

22–29 Aug

$197 SGD per night

Guest favourite

Barn in Eugenia

4.98 out of 5 average rating, 165 reviews

Blue Barn Bed n Bale / Blue Mountain

2 q. beds A relaxing farm stay on a working farm with or without your horses. Bright clean bunkie built in 2016 in our 160 year old barn. The space is new, cozy and offers a chance to spend hours of time with your horses or ours. Nothing like having coffee with your horses in the morning. We back on to 30,000 acres of trailed crown land and the Kolapore Trails lending itself to horseback riding, hiking, snow shoeing, atving, mountain biking. Check out the beautiful sunset behind the barn.

29 Sep – 6 Oct

$231 SGD per night

Guest favourite

Tiny home in Mono

4.94 out of 5 average rating, 152 reviews

Tiny home Soaring Heart Wellness Spa

A clean, bright space with high ceilings, privacy, and charm overlooking our Herbal Tea Garden. You can hike the Bruce Trail, relax by our pond or cycle through the Dufferin County Forest. Relax in the hot tub, book a massage, or enjoy a campfire under the stars. Check services online: Soaring Heart Wellness Inside is a bed, kitchenette, writing desk and sitting area. Outdoor is barbecue , firepit, and attached outhouse. Short walk to indoor bath Great local food and restaurants close by.

20–27 May

$81 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

$546 SGD per night

Guest favourite

Flat in Wasaga Beach

4.95 out of 5 average rating, 357 reviews

2 bedroom beachfront apartment

Lovely suite with its own 3 piece bathroom, living room with flat screen TV and kitchenette. Has its own deck, barbecue and entranceway overlooking the sandy shores of Georgian Bay. Steps to go swimming, kayaking or a sunset stroll. Parking available. No pets. Between June 30th - September 1st the apartment can only be rented by the week (check in & check out on Saturdays only). Outside of these dates, we are happy to host visitors with a minimum 1 night stay, check in/out any day of the week.

25 Nov – 2 Dec

$190 SGD per night

Guest favourite

Flat in Horning's Mills

4.96 out of 5 average rating, 255 reviews

Beautiful Riverside Country Apartment

Bright, warm and newly renovated, this 900sqft apartment, a private floor of a charming country home with separate entrance and garden patio, awaits you in Melancthon. SmartHDTV, Wifi, tranquil surroundings, and next to the Bruce Trail. Close to Shelburne, Mansfield, Creemore, and many excellent restaurants (like The Globe and Mrs Mitchels). Only 40 minutes to the Scandinave Spa, Collingwood, Blue Mountain, and Wasaga Beach. Golf Courses are close by. A perfect retreat just north of Toronto.

5–12 Sep

$110 SGD per night

Guest favourite

Guest suite in Collingwood

4.92 out of 5 average rating, 1010 reviews

Tiny Home Tranquility

Tiny Home Tranquility! Located just 15 minutes from Blue Mountain Ski Resort and Wasaga Beach. Walking distance to Collingwood downtown core and Georgian Bay . A custom built tiny home with all the amenities needed for a perfect getaway. This clean, bright and cozy tiny home is private and is attached to the main house with a breezeway to comply with the town bylaws. The Tiny Home has a separate entrance and private back patio giving guests total privacy. Absolutely no pets due to allergies.

6–13 Jan

$169 SGD per night

Guest favourite

Loft in Midland

4.88 out of 5 average rating, 286 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.

11–18 Jun

$189 SGD per night

Superhost

Cabin in Washago

4.82 out of 5 average rating, 221 reviews

The Islandview

Welcome to The Islandview! Located on the sandy shores of Lake Couchiching, this gorgeous 4 season, 2-story open concept cottage is the perfect getaway. Escape to the private sun filled deck or dock on the water. Entertain in the open concept kitchen, two large living areas, or outdoors around the fire. During the day, enjoy watching the kids swim on the beach and at night take in the breathtaking sunsets. 5min to Washago & 10min to Casino Rama. Fully equipped with everything you need!

23–30 Oct

$239 SGD per night

Guest favourite

Cabin in Bala

4.93 out of 5 average rating, 169 reviews

Cabin Medora Lake, Bala

Our place is close to Bala and Port Carling. You’ll love it! It's a big, one room, family cabin on a 6 acre forested property with a 40 sec. walk to our 1100 ft of shoreline on pristine Medora lake, with dock, canoe, great swimming and fishing. This place is good for couples or a family (with kids). A true Muskoka experience. The friendly and quiet owners who live next door have loved this incredible private property for 30 years and will ensure you have all the comforts you need.

6–13 Apr

$264 SGD per night

Guest favourite

Cottage in Bracebridge

4.9 out of 5 average rating, 438 reviews

Cottage on the Muskoka River

The cottage has a nice private setting as part of a parcel of land which is almost 20 acres along the Muskoka River, close to 3 waterfalls and on the Trans Canada Trail. You’ll love our place because of the access to many trails for hiking, yet only a few minutes to downtown Bracebridge and central to most Muskoka Attractions. To really enjoy the river location you need to love walking and exploring. The cottage is offered in its pre-renovation state as the pictures indicate.

22–29 Oct

$186 SGD per night

Guest favourite

Flat in Innisfil

4.99 out of 5 average rating, 495 reviews

Cozy One bedroom Apartment by the Lake

A clean and inviting upper level one-bedroom apartment across the street from beautiful Lake Simcoe & Innisfil Beach Park! A short walk to all amenities in town, (Tim's, LCBO, Pizza, Nofrills, Canadian Tire & More) just 20 minutes to Barrie and 50 minutes to Toronto. This apartment is perfect for a summer weekends to the beach. Also ideal for ice fishing in winter. You have your own private outdoor space with a BBQ and plenty of parking for car & boat.

28 Sep – 5 Oct

$104 SGD per night