Pet-friendly holiday rentals in Grey Highlands

Find and book unique pet-friendly homes on Airbnb

Top-rated pet-friendly home rentals in Grey Highlands

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

0 of 0 items showing

1 of 3 pages

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

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

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.

31 Aug – 7 Sep

$223 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.

29 Aug – 5 Sep

$110 SGD per night

Guest favourite

Tiny home in Meaford

4.96 out of 5 average rating, 148 reviews

Luxury Vintage Tiny House Farm Stay with Hot tub

Very unique cozy Airstream tiny home with BRAND NEW HEAVY DUTY FURNACE & electric fireplace - stay warm all winter long! Relax in your own private hot tub after a day of adventures. Snowshoes, firepit & BBQ available to enjoy while you watch the sunset, firewood included. Full kitchen, queen bed & 3 piece bathroom. There are friendly potbelly pigs on site for you to visit. Located 2 min from Meaford, close to Blue Mtn, beaches, ski clubs, Bruce Trail, waterfalls, scenic lookouts & more.

31 May – 7 Jun

$249 SGD per night

Guest favourite

Chalet in Grey Highlands

4.94 out of 5 average rating, 106 reviews

Private 5 Acre Chalet with Bunkie & Sauna

An enchanting, private, 4 season retreat in the escarpment atop Beaver Valley, metres from a beautiful section of the Bruce Trail. The property has nearly 5 acres with cut trails, hammocks, and a sports field. It has two buildings connected by a large deck that has outdoor furniture and a BBQ. The sauna is just feet away. The buildings are fully outfitted offering a comfortable base for daily adventuring, or a stay put retreat. This spot is ideal for a family, or a couple's getaway.

17–24 Sep

$173 SGD per night

Superhost

Tiny home in Meaford

4.85 out of 5 average rating, 257 reviews

Tiny Home Nestled between Thornbury & Meaford

Tiny home situation 10 min to Thornbury and 10 min to Meaford, and 20 min from Blue Mountain Village, nestled a country/residential area. Has all the basic comforts including spacious 3 piece bathroom. Close drive to beaches and many hikes and cross country ski trails in the area. It is also a 15 minute drive from Beaver Valley Ski Club and a number of different cideries. Shared pool available for the summer months with possibilities of covid restrictions. INTERNET just upgraded!

20–27 Mar

$134 SGD per night

Guest favourite

Cottage in Elmwood

4.97 out of 5 average rating, 109 reviews

Little Red Cabin on the River

Bright and cozy, open concept cabin retreat overlooking Styx river in beautiful West Grey. Relax next to a quiet river on a large lot with elevated deck, natural wood-burning fire pit and BBQ. This all season get away is 2 hours from Toronto, perfect for small families or a small group. Recently updated, this cabin features simple, modern decor with a fully furnished kitchen for home cooked meals and baking. Also now includes WiFi and an outside wood burning, cedar barrel sauna.

2–9 Mar

$236 SGD per night

Guest favourite

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.

2–9 Dec

$441 SGD per night

Guest favourite

Farm stay in Markdale

4.99 out of 5 average rating, 124 reviews

Experience Country Living at Firefly Ridge

Your private living space is comfortable and bright, with lots of picturesque windows and high ceilings. There is a walkout to a private area where you can relax, and unwind, enjoying the sounds of nature and some farm animals, such as horses, minis, donkeys, goats, chickens, cats, 2 Australian cattle dogs and even some piggies. We love our animals and we welcome yours as we are a pet friendly farm. Please note DOGS MUST be on a leash when on the property.

20–27 Nov

$197 SGD per night

Guest favourite

Guest house in Southgate

4.88 out of 5 average rating, 137 reviews

Cozy, quiet, clean cabin. With wi-fi.

Welcome to Penny Creek, a simple cabin just south of Durham. A private location surrounded by ponds / streams and forest - yet close to many day adventures should you want to explore beyond the property. Nearby amenities include restaurants / grocery / lcbo / fuel, coffee and shopping . An Open concept space that offers one queen bed and a pull out sofa. Full kitchen and bath. Picnic tables, Fire pit and bbq. Excellent hiking trails nearby!

2–9 Oct

$131 SGD per night

Guest favourite

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.

22–29 Jan

$316 SGD per night