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Cottage vacation rentals in Grey Highlands

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Top-rated cottage rentals in Grey Highlands

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Cottage in Meaford

4.92 out of 5 average rating, 159 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.

Cottage in Wasaga Beach

4.94 out of 5 average rating, 216 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!

Cottage in Meaford

4.9 out of 5 average rating, 199 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.

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.

Cottage in Kimberley

4.85 out of 5 average rating, 330 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

Cottage in Elmwood

4.98 out of 5 average rating, 127 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.

Cottage in Southgate

4.9 out of 5 average rating, 100 reviews

Thistle And Pine Cottage

Relax and unwind with the whole family at this peaceful place in the country. The cottage is on 50 acres that you have full access to. Great for swimming, walking, biking, cross country skiing, and much more. This 1 bedroom plus pullout couch(with privacy) is complete with kitchen, bathroom, and livingroom, and swimming pond with beach and Fire pit area that overlooks the pond. Perfect for a family of 4 or a romantic getaway for 2. Find us on Instagram @thistleandpine.cottage

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.

Cottage in Flesherton

4.87 out of 5 average rating, 100 reviews

The Golden Getaway

Enjoy this newly renovated modern cottage centrally located in Eugenia. Walking distance to the falls and the lake. Enjoy fresh baked goods and the best iced coffee around at garage13 just 2 minute walk from us or stop by top of the rock to grab your favourite beverage & snack for the night , then soak up all the stars in the open sky around the fire pit in the backyard. Bring the boats and floats , Boat launch provided for guests to enjoy all the amenities.

Cottage in Torrance

4.97 out of 5 average rating, 216 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.

Cottage in Tiny

4.94 out of 5 average rating, 242 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

Cottage in Kimberley

4.91 out of 5 average rating, 300 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.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

Popular amenities for Grey Highlands cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Flesherton

5 out of 5 average rating, 42 reviews

Greenery Lane - w/ private pond, hot tub & sauna!

Cottage in Gravenhurst

4.83 out of 5 average rating, 166 reviews

Trenanthia "Cahoots" Cottage: HotTub,Sauna,GamesRm

Cottage in Tiny

4.86 out of 5 average rating, 219 reviews

PrivateBeach@ThunderBeach100 acres Georgian Bay

Cottage in Flesherton

4.95 out of 5 average rating, 38 reviews

Four Season Waterfront Cottage on Lake Eugenia

Cottage in Port Severn

4.94 out of 5 average rating, 136 reviews

Muskoka Cottage on warm lake - 3 BR/2 BR/Hottub

Cottage in Flesherton

4.92 out of 5 average rating, 90 reviews

Sunset Cottage Lake Eugenia Hot Tub 4 Seasons

Cottage in Innisfil

4.87 out of 5 average rating, 122 reviews

Spacious family cottage 45 mins from GTA!

Cottage in Orillia

4.87 out of 5 average rating, 100 reviews

FRIEND LAKE HOUSE

Pet-friendly cottage rentals

Cottage in Flesherton

5 out of 5 average rating, 5 reviews

Hawthorn Cottage #5 - 3 Bedroom

Cottage in Gravenhurst

4.88 out of 5 average rating, 114 reviews

Waterfront 3 BR Cottage 4 Seasons Gravenhurst Heat

Cottage in Gravenhurst

4.92 out of 5 average rating, 141 reviews

Waterfront @Muskoka Pines /kayaks/bbq/firepit

Cottage in Washago

4.87 out of 5 average rating, 119 reviews

Vintage Farmhouse Lakeview and Golfers Cottage

Cottage in Waubaushene

4.81 out of 5 average rating, 150 reviews

The Cottage on Coldwater; where bay & trail meet.

Cottage in Innisfil

4.99 out of 5 average rating, 113 reviews

❤️ Charming Cottage/Lake View/10PPL/5BDR/3BATH

Cottage in Port Severn

4.92 out of 5 average rating, 101 reviews

Tree Tops on Six Mile Lake

Cottage in Waubaushene

4.95 out of 5 average rating, 129 reviews

Forest Harbour Hideaway

Private cottage rentals

Cottage in Berkeley

4.83 out of 5 average rating, 53 reviews

Fortress of Solitude

Cottage in Wasaga Beach

4.85 out of 5 average rating, 33 reviews

Wasaga Beach 1 BR basement -BBQ/POOL/AC

Cottage in Kimberley

4.86 out of 5 average rating, 73 reviews

Kimberley hillside chalet with hot-tub

Cottage in Holland Centre

5 out of 5 average rating, 57 reviews

Riverfront Hideaway*Hot Tub*Games Room*Firepit*BBQ

Cottage in Meaford

4.95 out of 5 average rating, 44 reviews

Entire Cottage with Hot Tub, near Beach

Cottage in Flesherton

4.84 out of 5 average rating, 19 reviews

Cottage Retreat on 11 Acres

Cottage in Flesherton

5 out of 5 average rating, 6 reviews

Waterfront Cottage #2

Cottage in Mulmur

5 out of 5 average rating, 71 reviews

The Squire's Cottage

Quick stats about cottage rentals in Grey Highlands

Total rentals
90 properties
Nightly prices starting at
$60 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

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