Pet-friendly holiday rentals in Grey Highlands

Vintage School House ~ Family, Pets, Hiking

Gather with family or friends in this vintage 5 bedroom School House in the Beaver Valley. -Ideal location to come together, relax, & connect. -Central heat & AC. -Take in the spectacular views of the Beaver Valley. -Explore the Niagara Escarpment and lookouts of the Bruce Trail. -Relax and read by the fireplace. -5 min walk to our swimming pond with dock & beach. -Convenient drive to groceries and local villages. -25 min drive to the Blue Mountains. -Reliable, consistent high speed internet.

Loft Where City Meets Country With Hot Tub

This unique place has a style all its own, while situated on a very private 39 acres where city style meets country living. The industrial apartment has been designed inside of a large building and offers all the luxuries of real glamping. Comfort and style throughout, complete with hotel quality mattress and linnens. The forested trails and beautiful property are a nature lovers paradise. You will find everything needed for a perfect getaway rather walking the trails or relaxing by the pond!

Secluded Cabin overlooking Valley.

Our comfy one-room cabin sits on the edge of 40 wooded acres, overlooking a pastoral valley. Enjoy a relaxing breakfast (included) on the deck while taking in the countryside view, and in the evening, lose yourself in the deep, dark, star-studded sapphire sky. A great home base as you experience the area - hiking beaches, waterfalls, cideries, vineyards and wineries. See more things to do at visitgrey. ca. Or stay put and enjoy your secluded getaway. Read a book, take a hike, or have a nap.

Aframe cabin by babbling brook with sauna & hottub

Cabin partially OFF GRID in winter months (Nov 1-May 7) No running water/shower/indoor bathroom at this time. Water is provided with water dispenser/maintained outhouse *Wood hot tub replaced in 2025 with nordic spa *Cabin situated on heavily treed 1 acre property with a creek directly in front of a quiet municipal road *Wood stove remains off-limits during the summer season (June-September). Wood & kindling provided for fall/winter use *No firewood provided for firepit/guests to pick up

Blue Mountain Gallery Getaway

Welcome to a cozy family escape featuring a stunning gallery wall showcasing scenic photography of South Georgian Bay. This peaceful retreat is just minutes from Blue Mountain Village or downtown Collingwood. Listen to the soothing sounds of the Cranberry Marsh Wetland, or walk to nearby Georgian Bay. Whether you’re hitting the slopes, the spas or the shops, unwind in a space that’s as inspiring as it is relaxing. Send us a message if you have any questions — we're always happy to help!

Tiny Home Nestled between Thornbury & Meaford

Tinyhome situated 10 min to Thornbury and Meaford, and 20 min from Blue Mountain Village, nestled a country/residential area so it is quiet and dark at night. 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 heated pool available for the summer months. Window Aircon/pool opens end of May or June.

Sundance of Blantyre Lodge +Hot Tub +Sauna +Pond

Welcome to Sundance of Blantyre! Step back in time in this historic yet modernized Lodge! This 3600 sq. ft retreat on the Bruce Trail has Breathtaking Valley Views from your own Private Hot Tub & Fire Pit all the Way to Georgian Bay. We invite you to enjoy our truly unique and tranquil getaway with 6 bedrooms + Private Sauna House! With 3 firepits, swimmable/fishing pond, hiking, cross country skiing and snow shoeing + snowmobile/ ATV trail access at your door, Your adventure awaits!

Tiny A-Frame near the Bruce Trail

Find yourself nestled among pines trees just steps from the Bruce Trail! This 100 sq. ft. tiny A-Frame offers cozy comfort with two stackable twin beds that convert into a queen (side-by-side) when desired. Amenities include the essentials: BBQ, drinking and dish water, power box to charge devices and a small light, plus an outhouse with a composting toilet. Centrally located near Old Baldy Lookout, Beaver Valley, Blue Mountain and Duncan Caves. The perfect spot to relax and unwind!

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.

A Cozy Country Retreat *Indoor Hot Tub* Ski* Wi-Fi

30 minutes to Georgian Bay, 25 to Collingwood/Blue Mountain, and only 10 to Lake Eugenia's public beach. Our lovely, spacious, 5 Bed 5 bath retreat is nestled comfortably in the woods, convenient to almost every kind of activity and adventure. With 5 wash rooms and a large, INDOOR, jetted hot tub, it provides the perfect combination of convenience, relaxation, and outdoor adventure! BBQ, pool table, fireplace, fire pit, board games and high speed wifi. INSTA: @HIDDENHIDEOUTS

All-Season Cottage 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.

Bayview Oasis: Luxe Lakeside Escape w/ Pickleball

Welcome to Bayview Oasis, our luxurious lake house on Georgian Bay. Enjoy breathtaking water views, a modern kitchen with high-end appliances, a cozy basement with a pool table and bar, and a master suite with top-notch amenities. Outdoors, relax in the cabana with a pizza oven, fireplace, picnic tables, spacious patio, hot tub, and our new custom pickleball court. Whether it's a romantic getaway or family vacation, Bayview Oasis is the perfect retreat.