Cottage holiday rentals in Grey Highlands

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Top-rated cottage rentals in Grey Highlands

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Guest favourite

Cottage in Wasaga Beach

4.89 out of 5 average rating, 234 reviews

Cozy Riverfront Cottage Retreat with Dock / Ski

→Bright, 2 bedroom cottage with 1 queen, 1 twin bunk bed, 1 cot if needed →Comfortably sleeps up to four →Fantastic views up and down the Nottawasaga River →Air conditioning, Firepit →9 Minutes to the NEW Wasaga Beach Casino →Great fishing (Steelhead, trout, pike, salmon, bass, pickerel), boating, canoeing, kayaking →Central to skiing - Blue Mountain, Mount St Louis Moonstone, Horseshoe →Large Dock on the Nottawasaga river →On-premise parking for up to 3 vehicles →High-Speed unlimited internet

Guest favourite

Cottage in Meaford

4.92 out of 5 average rating, 157 reviews

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.

Guest favourite

Cottage in Wasaga Beach

4.94 out of 5 average rating, 213 reviews

Charming riverside cottage, walk to beach

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!

Guest favourite

Cottage in The Blue Mountains

4.93 out of 5 average rating, 117 reviews

Luxury Chalet in Blue Mountains with HotTub Sauna

*4 SEASONS COTTAGE*This newly renovated chalet in the heart of Blue Mountains accommodate16 people with 6 bedrooms,10 beds(2 queen, 1 twin,1 double and 3 double over double bunk beds)and 4 baths.This chalet comes with great features such as beach access,private backyard,all brand-new mattresses and beddings,pool table and ping pong table,arcade games,poker table 2 living rooms with TVs,sauna,hot tub and an indoor fireplace.4 minutes drive from Northwinds Beach.License number LCSTR20220000131

Guest favourite

Cottage in Meaford

4.91 out of 5 average rating, 198 reviews

Water's Edge - 4 Season Cottage

Comfy & cozy 3 bedroom year round cottage on the shores of Georgian Bay. Sleeps 6, washer/dryer, full kitchen w/dishwasher, living & dining w/fireplace, A/C, deck, BBQ, firepit & hot tub. Suits families with older children & couples. Lots of shopping, live entertainment, artisans & exquisite local fare. 30 min drive to Blue Mountain Village & the Spa. Close to the Bruce & Georgian Trails. Spectacular views of The Bay, The Blue Mountains and the best sunrises with your morning coffee.

Superhost

Cottage in Kemble

4.81 out of 5 average rating, 135 reviews

Georgian Bay Waterfront Oasis

Waterfront Cottage 15 mins north of Owen Sound on the crystal clear waters of Georgian Bay. We have 150 feet of private shoreline. Enjoy the east facing view and stunning sunrises, relax on a lounger, go for a swim, fish off the shore or in the small row boat, have a camp fire and stargaze. Use our cottage as a jumping off point for many hikes along the Bruce Trail, Sauble Beach (35min), Tobermory (70min) and many more. Or just work from here while enjoying the great view and wifi.

Guest favourite

Cottage in Kimberley

4.85 out of 5 average rating, 329 reviews

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

Guest favourite

Cottage in Elmwood

4.98 out of 5 average rating, 126 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.

Guest favourite

Cottage in Flesherton

4.94 out of 5 average rating, 136 reviews

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.

Guest favourite

Cottage in Torrance

4.97 out of 5 average rating, 215 reviews

Beautiful Nine Mile Lake

Beautiful Muskoka getaway! Modern 4 season waterfront cottage! Stunning views! Located on picturesque Nine Mile Lake. Over 70% of the lake is crown land. Perfect for kayaking and canoeing to enjoy all the beauty Muskoka is known for. We have kayaks a canoe and a paddle board for you to enjoy. Plenty of sun exposure on the dock you can swim all day long. Close to hiking and snowmobile trails. May 15-Oct 2 Minimum 6 nights with a Sunday check in.

Guest favourite

Cottage in Tiny

4.94 out of 5 average rating, 237 reviews

Bluestone

Bluestone is located less than 10 minutes' drive from beautiful Awenda Provincial Park in Tiny, Ontario. Every choice was made with guest comfort in mind. In the Summertime, take a short walk down a wooded path to Georgian Bay and perfect swimming, or explore a hiking trail and take in the natural beauty of the area. In Winter, enjoy skiing and snowshoeing locally, or stay in, put a record on, and cozy up by the fire. License #STRTT-2024-017

Guest favourite

Cottage in Kimberley

4.91 out of 5 average rating, 297 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.