Cottage holiday rentals in Grey Highlands

Summer Getaway - 3 min walk to Beach, Clean & Cozy

Insta: @woodwardbythebeach 3min walk to the area’s most beautiful beach, sunsets & trails, you'll be sure to get lost in the serenity of the sand dunes year round Outdoor fire pit- s'mores included! Enjoy the BBQ, deck, & patio; the wine is on us! Fast WIFI for streaming movies or work from cottage Area is secluded yet central. 10min to Midland, close to Balm Beach - arcade, gokart, restaurant, & bar Ski/Hike/Snowmobile then unwind in a peaceful winterized home getaway with indoor fireplace

Cosy and modern cottage on beautiful Georgian Bay

Enjoy panoramic views of Georgian Bay from this charming modern cottage on Paynter's Bay. Only eight minutes from Owen Sound, our cottage also borders on the quiet and beautiful Hibou Conservation Area where you can enjoy birding, hikes in forest and shoreline, and a great sandy beach and modern playground for the kids. Cuddle up next to the gorgeous modern Morso woodstove. Adventure awaits you with lots of skiing, biking, snowmobiling and the waterfall wonders of the Niagara Escarpment nearby.

Charming riverside cottage, B&B license

Charming riverside cottage available on Wasaga Beach. Just a 4-minute stroll from a pristine sand beach. Immerse yourself in nature's beauty while enjoying modern amenities, including a private hot tub for relaxation. Unwind with a friendly round of mini-golf or gather around the fire pit for cozy evenings under the stars.Create lasting memories at this perfect oasis that combines riverside tranquility, mini-golf fun, hot tub relaxation, and the warmth of a fire pit. Your dream getaway awaits!

Vintage School House ~Hiking, Skiing, Pet Friendly

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.

Luxurious Creek Retreat With Hot Tub

Welcome to this luxury cottage on the water. The perfect place to relax and unwind while listening to the waterfall and babbling brook flowing past only a few feet away. If you're looking for privacy and tranquility along with all the pleasures of a luxury stay then look no further. This property boasts a propane fireplace inside as well as one outside, in-floor heat and A/C. Fully equipped kitchen, two bedrooms with hotel quality mattresses and a bathroom that exudes high-end style and decor.

Ultimate Georgian Bay Vacation Getaway

Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

Cozy Riverfront Cottage with Dock

Escape to our cozy waterfront cottage on the Nottawasaga River in Wasaga Beach! This bright, airy retreat comfortably sleeps 4 and features a large private dock and fire pit both overlooking the river plus modern amenities, outdoor dining area and BBQ. Enjoy direct river access from the dock for fishing and boating. Perfectly located just minutes from the main Beach 1 and a short drive to Blue Mountain Ski Resort, Collingwood, Creemore and the Wasaga Casino. Your ideal getaway awaits!

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

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.

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.

Waterfront Cottage with Steam Sauna by Bruce Trail

Welcome to this stunning waterfront , cozy ,4 season cottage located on the edge of a cliff surrounded by the lake on one side and Bruce trail on the other. This private oasis is perfect for couples or families w. older kids where you can connect to nature but still stay close to the city. Walking distance to Bruce trail, short drive to Sauble Beach or Wiarton for shopping and dining, 25 min drive to Lions Head, 45 min to Tobermory. It's time to plan your visit to Bruce!!!

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.