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Cottage holiday rentals in Grey County

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Top-rated cottage rentals in Grey County

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, 134 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.

18–25 Nov

$301 SGD per night

Guest favourite

Cottage in Southgate

5.0 out of 5 average rating, 20 reviews

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.

12–19 Feb

$290 SGD per night

Guest favourite

Cottage in Meaford

4.91 out of 5 average rating, 181 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.

2–9 Jan

$578 SGD per night

Cottage in Kemble

4.83 out of 5 average rating, 118 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.

9–16 May

$143 SGD per night

Guest favourite

Cottage in Meaford

4.97 out of 5 average rating, 37 reviews

Entire Cottage with Hot Tub, near Beach

Updated, bright 2 BR cottage in Meaford On. Near the shores of Georgian Bay and steps from water access at a small public beach. Three beds (queen pull out in living room), washer/dryer, well stocked kitchen with dishwasher, wi-fi, TV, A/C, deck, BBQ, firepit & hot tub. Enjoy the many local attractions or stay home and unwind (<1hr to Sauble Beach, 35 min to Blue Mountain Village, 25-30 min to Beaver Valley or Georgian Peaks Ski Clubs). Suits small families, friends and couples.

22–29 Sep

$187 SGD per night

Guest favourite

Cottage in Kimberley

4.87 out of 5 average rating, 307 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

3–10 Jul

$761 SGD per night

Guest favourite

Cottage in Flesherton

4.97 out of 5 average rating, 35 reviews

Family Oasis on Lake Eugenia

Come relax and make lasting memories with family and friends at our oasis on Lake Eugenia! We have a total of 5 bedrooms and 3.5 bathrooms, between our main cottage and bunkie. Take a dip in the hot tub or enjoy the wood fired sauna. Cozy up by the bonfire and relax with a good book. Use the fully equipped kitchen and bbq with provided propane. We also have 1 canoe, 2 kayaks, 2 paddle boards, and lots of space on the lawn for games. Our space is ideal for families, not parties.

5–12 May

$471 SGD per night

Guest favourite

Cottage in Elmwood

4.97 out of 5 average rating, 109 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.

9–16 Nov

$234 SGD per night

Guest favourite

Cottage in Southgate

4.89 out of 5 average rating, 79 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

19–26 Nov

$154 SGD per night

Cottage in Flesherton

4.73 out of 5 average rating, 30 reviews

Cozy 3 Bedroom Cottage Retreat.

Relax with family or a group of friends at this peaceful getaway located in the little town of Eugenia. Explore Lake Eugenia with a deeded access less than a 3 minute walk from the cottage or spend the day chasing waterfalls. Eugenia falls is within walking distance of the Cottage or head to Hoggs falls which is only a 10 minute drive from Cottage. We are also minutes away from many amazing hikes along the Bruce Trail. Our Cottage has everything you need for your next getaway!

28 Oct – 4 Nov

$230 SGD per night

Guest favourite

Cottage in Flesherton

4.94 out of 5 average rating, 122 reviews

Cottage Get-Away 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.

27 Nov – 4 Dec

$437 SGD per night

Guest favourite

Cottage in Kimberley

4.9 out of 5 average rating, 267 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.

21–28 Jun

$307 SGD per night

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

Flats

Convenient locations with everyday essentials

Chalets

Adventure-ready homes with après-ski style

Popular amenities for cottage rentals in Grey County

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Meaford

4.72 out of 5 average rating, 357 reviews

The Surf Shack - Hot Tub, G-Bay Beach Access

19–26 Jan

$316 SGD per night

Guest favourite

Cottage in Holland Centre

5.0 out of 5 average rating, 44 reviews

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

8–15 Dec

$420 SGD per night

Guest favourite

Cottage in Annan

4.98 out of 5 average rating, 52 reviews

Private 5 Acres Lakefront Cottage - Georgian Bay

4–11 May

$517 SGD per night

Cottage in Kimberley

4.87 out of 5 average rating, 63 reviews

Kimberley hillside chalet with hot-tub

19–26 May

$374 SGD per night

Guest favourite

Cottage in Flesherton

4.95 out of 5 average rating, 42 reviews

Outdoor Paradise, Walk to the Lake, Hiking, Biking

22–29 Sep

$495 SGD per night

Guest favourite

Cottage in Meaford

5.0 out of 5 average rating, 27 reviews

Serenity Cottage, Hot Tub, Jetski, Sauna, Icerink

16–23 Jan

$669 SGD per night

Cottage in Meaford

4.95 out of 5 average rating, 22 reviews

Skipping Rock Cottages ~ Stunning Lakeside Getaway

8–15 May

$712 SGD per night

Guest favourite

Cottage in Flesherton

5.0 out of 5 average rating, 34 reviews

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

13–20 Oct

$559 SGD per night

Pet-friendly cottage rentals

Guest favourite

Cottage in Flesherton

4.94 out of 5 average rating, 64 reviews

The Golden Getaway

3–10 Jun

$329 SGD per night

Guest favourite

Cottage in Meaford

4.95 out of 5 average rating, 77 reviews

Cottage w/Pool on Mountain (3+ private acres)

1–8 May

$271 SGD per night

Guest favourite

Cottage in Georgian Bluffs

5.0 out of 5 average rating, 57 reviews

Mossy Rock Getaway, for a tranquil retreat.

25 Jan – 1 Feb

$211 SGD per night

Guest favourite

Cottage in Meaford

4.95 out of 5 average rating, 41 reviews

Charming 3bdrm cottage on Georgian Bay!

1–8 Jan

$339 SGD per night

Guest favourite

Cottage in Chatsworth

4.97 out of 5 average rating, 33 reviews

Luna Log House - forest retreat with outdoor sauna

29 Aug – 5 Sep

$635 SGD per night

Guest favourite

Cottage in Elmwood

4.95 out of 5 average rating, 42 reviews

Family Cottage On Quiet Lake w/ Shallow Entry

16–23 Jun

$483 SGD per night

Guest favourite

Cottage in Meaford

5.0 out of 5 average rating, 20 reviews

New and Cozy Cottage Minutes to Blue Mountain

27 Jan – 3 Feb

$244 SGD per night

Guest favourite

Cottage in Georgian Bluffs

4.96 out of 5 average rating, 54 reviews

Georgian Bay-Pristine Waterfront 4 Season Cottage

17–24 Sep

$572 SGD per night

Private cottage rentals

Guest favourite

Cottage in Meaford

5.0 out of 5 average rating, 20 reviews

Georgian Bay Waterfront Cottage

2–9 Oct

$297 SGD per night

Guest favourite

Cottage in Meaford

4.96 out of 5 average rating, 25 reviews

The Avalon - Entire home steps to Meaford Harbour

1–8 Dec

$420 SGD per night

Guest favourite

Cottage in Meaford

4.89 out of 5 average rating, 73 reviews

Cozy waterfront cottage on Georgian Bay

1–8 Oct

$413 SGD per night

Guest favourite

Cottage in Mildmay

5.0 out of 5 average rating, 10 reviews

Welcome to ‘The AnnaBelle’

27 Jun – 4 Jul

$228 SGD per night

Guest favourite

Cottage in Wiarton

4.98 out of 5 average rating, 88 reviews

Waterfront Cottage by Bruce Trail

17–24 Jul

$482 SGD per night

Guest favourite

Cottage in Wiarton

4.94 out of 5 average rating, 17 reviews

Stunning lakefront cottage

28 Jan – 4 Feb

$328 SGD per night

Guest favourite

Cottage in Elmwood

4.94 out of 5 average rating, 32 reviews

Lakefront Family Cottage on Quiet Private Lake

20–27 Mar

$760 SGD per night

Guest favourite

Cottage in Meaford

4.93 out of 5 average rating, 59 reviews

Aquavista Waterfront - Georgian Bay Cottage

2–9 Dec

$617 SGD per night

Destinations to explore