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Cottage holiday rentals in Grey Highlands

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Top-rated cottage rentals in Grey Highlands

Guests agree: these cottages are highly rated for location, cleanliness and more.

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Cottage in Meaford

4.93 out of 5 average rating, 161 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, 219 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 Wiarton

4.92 out of 5 average rating, 50 reviews

Waterfront Cottage for rent (Near Sauble Beach)

Waterfront cottage on Lake Huron, perfect vacation rental for families or groups looking to escape to a serene paradise. Mins from SawMill Ski Trails. 3 bedrooms & breathtaking waterfront views, cottage is the ideal choice for a family vacation, a romantic getaway, or a group trip with friends. Relax on the private deck and take in the stunning views of the lake, or take a dip in the crystal-clear waters. With a view of lake from Hot tub, this cottage is the ultimate vacation destination.

Cottage in Meaford

4.85 out of 5 average rating, 13 reviews

Lovely Country Cottage near Georgian Bay

Nestled on a hill sits our updated cheerful family cottage. Our area of Georgian Bay offers amazing swimming in the summer, and great skiing in the winter! Some of the best hiking at the Tom Thompson trail and the Bruce trail, great fishing spots at big head river, wineries, breweries and cideries all within a short driving distance. Our cottage is a 5 minute drive from the town of Meaford. 15 minutes to Thornbury, 30/35 minutes to Blue Mountain/Beaver Valley /Georgian Peaks ski clubs.

Cottage in Tiny

4.88 out of 5 average rating, 105 reviews

The Lakeview cottage w/ hot tub

Welcome to our 4 season, 2 family cottage with Georgian Bay views and a hot tub. 3 min walk to the cutest small beach that has stunning sunsets, 12 min to Awenda Provincial Park which has great hiking, beaches, biking and winter activities. Short drive to Balm Beach. Downtown Midland has great restaurants and everything a quaint downtown has to offer. Winter has so much to offer including ice fishing, OFSC snowmobile trails, cross country skiing and much more. Max occupancy is 8 adult.

Cottage in Tobermory

4.88 out of 5 average rating, 107 reviews

7BR near Tobermory w/Golf Sim, Game Room & Hot Tub

Escape to a world of peace and tranquility at our private and secluded farmhouse-style cottage located in Wiarton. Surrounded by lush trees, this cottage offers the perfect retreat for families or friends. It's the ideal place for making memories. Great entertainment space, hot tub, NEW GOLF SIMULATOR and a cozy fireplace to gather around. On warm nights, relax on the large patio deck and gaze at the stars. This is a place you won't forget and will want to return to again and again.

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, 217 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 Grey Highlands

4.92 out of 5 average rating, 157 reviews

Hilltop garden cottage

enjoy a relaxing stay at a rustic family cottage with open concept for entertaining.relax in front of the fireplace with a glass of wine.Enjoy a morning coffee on the upper deck with a views of the gardens and lower deck for your family dinner in a peaceful setting . 2 minute walk to the lake at beach and boat launch or enjoy the many hiking trails including the Bruce trail with stunning views of Beaver Valley with local water falls.

Guest favourite

Cottage in Tiny

4.82 out of 5 average rating, 34 reviews

Cozy cottage on a private beach / Georgian Bay

Welcome to Sandalwood Cottage! Just 1.5 hours from Toronto, our spacious 5-bedroom retreat is a 5-min walk from a private beach on Georgian Bay. Perfect for families, it sleeps up to 13 and features a wrap-around deck for BBQs and relaxation. Enjoy hiking, biking, and canoeing in summer, or snowmobiling, skiing, and skating in winter. A peaceful escape with Wasaga Beach only 15 minutes away. Book your perfect getaway today!

Cottage in Tiny

4.81 out of 5 average rating, 149 reviews

Tiny Beach Cottage

Beautiful, newly-renovated 6 bedroom cottage. All of the modern comforts of a home while maintaining the cottage feel you expect when trying to escape the busy city life. Situated on a "no exit" road resulting in a peaceful and quite area. Cottage has a central air conditioning and furnace ideal for all seasons. Featuring two large decks, perfect for outdoor dining or relaxing. STRTT-2024-126

Cottage in Tiny

4.86 out of 5 average rating, 219 reviews

Winter Wonderland! GB 100 acres Snowshoe Paradise!

THIS IS NOT a waterfront cottage, but it includes a separate PRIVATE gated beach LAKEFRONT property for your EXCLUSIVE USE! Our private two-acre gated beach at Marks Point, the western tip of Thunder Beach, is ten minutes by car from the cottage. The second beach option (public) is the unsurpassed 3km sand Thunder Beach, 5 minutes by foot! The cottage is on our private 100 acres.

Holiday rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Houses

A space that's all yours, with room for everyone

Popular amenities for cottage rentals in Grey Highlands

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Guest favourite

Cottage in Kimberley

4.85 out of 5 average rating, 331 reviews

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

Guest favourite

Cottage in Tiny

4.96 out of 5 average rating, 223 reviews

Private 40 Acre Cottage with Hot Tub

Guest favourite

Cottage in Severn Bridge

5 out of 5 average rating, 108 reviews

CozyPeaceful LakeCottage HotTub CheckOutOurReviews

Cottage in Gravenhurst

4.82 out of 5 average rating, 169 reviews

Trenanthia "Cahoots" Cottage: HotTub,Sauna,GamesRm

Guest favourite

Cottage in Waubaushene

4.87 out of 5 average rating, 440 reviews

Charlie the Cottage | Hot Tub | Trail | Hike/Run

Guest favourite

Cottage in Gravenhurst

4.97 out of 5 average rating, 192 reviews

Muskoka Oasis: Hot Tub, Sauna & Nature Retreat

Guest favourite

Cottage in Innisfil

4.9 out of 5 average rating, 158 reviews

Stunning Lakefront Cottage Hot Tub & Sauna

Cottage in Orillia

4.87 out of 5 average rating, 101 reviews

FRIEND LAKE HOUSE

Pet-friendly cottage rentals

Guest favourite

Cottage in Meaford

4.95 out of 5 average rating, 92 reviews

Woodski Mountain Retreat w/Pool & 3+ Private Acres

Guest favourite

Cottage in Tiny

4.94 out of 5 average rating, 142 reviews

Cozy 4 Season Family Cottage

Guest favourite

Cottage in Gravenhurst

4.88 out of 5 average rating, 114 reviews

Waterfront 3 BR Cottage 4 Seasons Gravenhurst Heat

Guest favourite

Cottage in Wiarton

5 out of 5 average rating, 18 reviews

MoonShadow 4 Season Cottage Near Sauble Beach

Guest favourite

Cottage in Gravenhurst

4.98 out of 5 average rating, 60 reviews

Muskoka Beach Chalet!

Cottage in Sauble Beach

4.72 out of 5 average rating, 72 reviews

My Blue Haven - Sauble Beach, Ontario

Guest favourite

Cottage in Tiny

4.87 out of 5 average rating, 38 reviews

Balm Beach Cottage: Hot Tub/GameRoom/more!

Guest favourite

Cottage in Sauble Beach

4.93 out of 5 average rating, 28 reviews

Sauble Beach - Quiet 4 Season Cottage Near Beach

Private cottage rentals

Guest favourite

Cottage in Wasaga Beach

4.9 out of 5 average rating, 21 reviews

The River's Edge - Cottage 1: The Riverbank House

Guest favourite

Cottage in Howdenvale

4.89 out of 5 average rating, 44 reviews

Beautiful Private Cottage on 10 Acres and a view!

Guest favourite

Cottage in Southgate

4.9 out of 5 average rating, 100 reviews

Thistle And Pine Cottage

Guest favourite

Cottage in Coldwater

4.97 out of 5 average rating, 38 reviews

Charming 3BR Cottage on Tranquil Lake 🐦🛶🎣🏊‍♀️

Guest favourite

Cottage in Tiny

4.97 out of 5 average rating, 36 reviews

2 Bedroom Plus Bunkie Woodland Beach Cottage

Cottage in Sauble Beach

4.88 out of 5 average rating, 26 reviews

Sauble Beach Front Cottage 2

Guest favourite

Cottage in Palgrave

4.99 out of 5 average rating, 207 reviews

Hockley valley, up country guest cottage

Cottage in Kemble

4.81 out of 5 average rating, 135 reviews

Georgian Bay Waterfront Oasis

Quick stats about cottage rentals in Grey Highlands

Total rentals
90 properties
Nightly prices starting at
₹5,097 before taxes and fees
Total number of reviews
3.2K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace

Destinations to explore