Family-friendly vacation rentals in Grey Highlands

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Top-rated family-friendly rentals in Grey Highlands

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

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Guest favorite

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.

Sep 20 – 27

ﺩ.ﺇ616 per night

Guest favorite

Guest suite in Chatsworth

4.85 out of 5 average rating, 349 reviews

Settler's Loft in Log Home

This charming original log home is set amongst rock fences and mature maples on 80 acres of reforested farmland. This two-storey suite sleeps up to 5 guests, has 2 bedrooms, 4-piece bathroom, kitchenette, living area, deck, & private balcony. Trails for exploring, campfire ring, and large grassy area for outdoor games. Brand new AC system. Very close to OFSC snowmobile trails. (Note - barn access is for weddings only) NO pets >> 40 minute drive to Blue Mountain; 30 minutes to Lake Huron beaches

Mar 24 – 31

ﺩ.ﺇ393 per night

Guest favorite

Guesthouse 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.

Oct 15 – 22

ﺩ.ﺇ570 per night

Guest favorite

Chalet in Priceville

4.91 out of 5 average rating, 448 reviews

ReLive Hilltop Chalet w/brand-new hottub, sunrises

Relive Retreat's Hilltop Chalet is a 700 sq ft open concept rustic cabin w/high ceilings, full-length windows, spring water, private + new hot tub, fireplace, BBQ, wrap around deck w/views, hiking trails + more. Perfect for couples, friends or families looking to relax & rejuvenate in nature. If peace is what you are looking for this is it! Occassionally dog friendly so please inquire first. This is a private 72 acre retreat. We live here with our 2 dogs, currently hosting 2 yurts and 2 cabins.

Sep 24 – Oct 1

ﺩ.ﺇ595 per night

Guest favorite

Apartment 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.

Jul 8 – 15

ﺩ.ﺇ292 per night

Guest favorite

Guest suite in Collingwood

4.92 out of 5 average rating, 1011 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.

Jan 10 – 17

ﺩ.ﺇ450 per night

Guest favorite

Cabin in Owen Sound

4.97 out of 5 average rating, 226 reviews

Cozy 'Off the Grid" Rustic Cabin

If you enjoy 'roughing it', stay in our beautiful log home from the late 1800's. It has been completely redone, maintaining all of the old character. It is nestled in the edge of the bush, that provides kilometres of hiking trails. The cabin is also situated on a pond so you can spend your days swimming, canoeing, fishing and exploring this nature lover's paradise. Spend your time here unplugging from your everyday life and reconnecting to the healing properties of a natural environment.

Jan 27 – Feb 3

ﺩ.ﺇ534 per night

Guest favorite

Guest suite in Holland Centre

4.97 out of 5 average rating, 194 reviews

Dragonfly Hollow bnb

Nature lovers, Come experience the natural beauty of the Grey-Bruce region. Our home is in a very quite natural setting surrounded by trees. In summer explore the many lakes, beach or waterfalls . Hike the Bruce trail, or one of many others; good for ATVing, Scenic Motorcycle Routes. Fall is especially beautiful, the hills and valleys fill with vibrant colours. In winter, enjoy cross-country, downhill skiing, snowboarding, skidooing. Blue Mountain only a Scenic 40 mins away.

Dec 17 – 24

ﺩ.ﺇ306 per night

Guest favorite

Cottage in Flesherton

4.94 out of 5 average rating, 122 reviews

Cottage Get-Away on the Lake

An entire cottage all to yourself right on the water of Lake Eugenia in the Grey Highlands. This fully furnished 3-bedroom cottage is equipped with a brand-new kitchen, appliances, wood burning stove, furnace and water heater. You'll also have FREE access to unlimited WiFi, so you can work or stay in touch, when needed. Our cottage is suitable for a great get-away with any group, family or friends who are looking for a peaceful and enjoyable holiday from their busy lives.

Aug 31 – Sep 7

ﺩ.ﺇ1,055 per night

Guest favorite

Cottage in Kimberley

4.9 out of 5 average rating, 267 reviews

School House Retreat •Hiking •Pets •Campfire •WiFi

Enjoy this unique renovated School House as a safe space to gather as a family or group. Independent and remote, the School House is located in the beautiful Beaver Valley, near the Blue Mountains. With reliable, consistent high speed internet, and a close drive to groceries and towns with essential needs, the School House is an ideal location to come together, relax, connect, and explore the trails and stunning views of the Niagara Escarpment.

Feb 17 – 24

ﺩ.ﺇ855 per night

Guest favorite

Home in Kimberley

4.88 out of 5 average rating, 176 reviews

Heart of Kimberley - with views and a hot tub

Welcome to the hamlet of Kimberley nestled in the Beaver Valley. Surrounded by nature, the Rock House is a historic six bedroom century home with beautiful views close to many outdoor activities, and located beside an unassuming gourmet restaurant and a general store with fresh coffee and in-house sourdough bread. We are located 25 minutes from Blue Mountain and 2 minutes from Beaver Valley Ski Club.

Sep 16 – 23

ﺩ.ﺇ975 per night

Guest favorite

Guest suite in Orangeville

4.97 out of 5 average rating, 139 reviews

Your very own peaceful santuary in nature

Tranquil space to go walking through the 20 acres of forest with trails, lots of wildlife, and beautiful bright stars at night for stargazers. You can have a coffee in the morning on the patio set in front of the suite and have a drink on one of the hills in comfortable muskoka chairs up on a hill of the property and watch the sunset or sunrise if you are an early bird.

Oct 17 – 24

ﺩ.ﺇ306 per night