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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, 135 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

€ 240 per night

Guest favourite

Cottage in Wasaga Beach

4.96 out of 5 average rating, 135 reviews

Sanablue by the Bay -Stylishly Untrendy since 1958

Sanablue is a quiet out of the way escape for your family ... that's right next to everything that's great about Wasaga! Extra clean & sanitized. See reviews for our track record! Just 91 barefoot steps to the edge of Georgian Bay (yep, an 11 year old paced them of for us!). A 4 min stroll to grab a coffee (or a bottle of wine). Just meters to Oakview Woods hiking trails & Wasaga biking trails. 10 min to Collingwood. 15 min to breathtaking Blue Mountain ..... Or just put your feet up & relax.

27 May – 3 Jun

€ 144 per night

Guest favourite

Cottage in Tiny

4.94 out of 5 average rating, 118 reviews

Cozy 4 Season Family Cottage

***NEW LISTING*** 4 season cottage, 5 min walk to beaches. Approx 1300sq. feet including 3 bedrooms and 1 large bathroom. Accommodates 6-8 Comfortably. Large Wrap around deck with outdoor furniture and greenery provided and BBQ Area to keep you relaxed and at home. Outdoor fire pit available. Situated on a private lot surrounded by nature. This getaway is equipped with everything you need - appliances and utensils, linens, Wifi, TV, board games, laundry with plenty more to do in the area.

22–29 Sep

€ 172 per night

Cottage in Flesherton

4.81 out of 5 average rating, 272 reviews

Walk to the Beach * Outdoor Sauna * Hot Tub

Welcome to our cozy, comfortable (500 sqft) cottage, located in the beautiful Beaver Valley. Enjoy the outdoor sauna, hot tub, shower and fire circle. Grill and dine indoors or out. With the public beach and boat launch only minutes away, you'll find everything you need for a wonderful vacation. You'll love this cottage, which practically exudes charm and hospitality, both inside and out. Be sure, while you're here, to take in the five, beautiful area waterfalls! INSTA: /HIDDENHIDEOUTS

12–19 Aug

€ 279 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.

8–15 Jan

€ 407 per night

Cottage in Kemble

4.83 out of 5 average rating, 119 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

€ 109 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.

27 Feb – 6 Mar

€ 178 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.

25 Oct – 1 Nov

€ 248 per night

Guest favourite

Cottage in Port McNicoll

4.98 out of 5 average rating, 125 reviews

Boe's Cottage: Newly Renovated - Great WIFI

Experience Southern Georgian Bay - Ontario's Four Season Playground. Just 90 Minutes from Toronto! Relax in our fully renovated 4 season cabin with all the amenities of home. Steps from the lake with parks, beaches, hiking, kayaking. And in the winter, snowshoe, skate, snowmobile, cross country & downhill skiing at Mount st. louis moonstone Great setup for a 'working' vacation with excellent WIFI 10 Minutes to Midland for restaurants & unique shopping experiences

5–12 Oct

€ 130 per night

Guest favourite

Cottage in Tiny

4.94 out of 5 average rating, 206 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

18–25 Dec

€ 177 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.

16–23 Jun

€ 237 per night

Guest favourite

Cottage in Wasaga Beach

4.95 out of 5 average rating, 230 reviews

GATED RESORT COTTAGE

[CLICK SHOW MORE FOR IMPORTANT INFO] Sought-after cottage located in the gated Wasaga Country Life resort; professionally managed year-round by Parkbridge. A short walk from the beach with full access to resort amenities including; indoor/outdoor swimming pools, private trails, playgrounds, mini golf, sports fields and many more professionally managed facilities. View the "Where you'll be" section below for a full list of amenities.

8–15 Jan

€ 140 per night

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Chalets

Adventure-ready homes with après-ski style

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for cottage rentals in Grey Highlands

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Guest favourite

Cottage in Tiny

4.95 out of 5 average rating, 196 reviews

Private 40 Acre Cottage with Hot Tub

22–29 Jul

€ 384 per night

Guest favourite

Cottage in Wasaga Beach

4.93 out of 5 average rating, 190 reviews

Charming riverside cottage, walk to beach

26 Sep – 3 Oct

€ 311 per night

Guest favourite

Cottage in Midland

4.86 out of 5 average rating, 150 reviews

House on the Hill, HotTub, Ski, Ice Fish, Trails

18–25 Jan

€ 200 per night

Cottage in Waubaushene

4.86 out of 5 average rating, 396 reviews

Modern Cottage w/ Hot Tub on Trail - Hike/Run

14–21 Jul

€ 470 per night

Cottage in Tiny

4.86 out of 5 average rating, 219 reviews

Georgian Bay Cottage -100 acres & Private Beach

8–15 Dec

€ 184 per night

Guest favourite

Cottage in Port Severn

4.94 out of 5 average rating, 127 reviews

Muskoka Cottage on Gibson Lake - 5 BR/3 BATHS

4–11 Apr

€ 488 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 May

€ 347 per night

Guest favourite

Cottage in Southgate

5.0 out of 5 average rating, 20 reviews

Luxurious Creek Retreat With Hot Tub

22–29 Dec

€ 302 per night

Pet-friendly cottage rentals

Guest favourite

Cottage in Wasaga Beach

4.89 out of 5 average rating, 205 reviews

Cozy Riverfront Cottage Retreat with Dock / Ski

7–14 Oct

€ 267 per night

Cottage in Waubaushene

4.81 out of 5 average rating, 126 reviews

The Cottage on Coldwater; where bay & trail meet.

8–15 May

€ 130 per night

Guest favourite

Cottage in Tiny

4.96 out of 5 average rating, 109 reviews

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

22–29 Dec

€ 341 per night

Cottage in Lafontaine

4.8 out of 5 average rating, 196 reviews

Beach house (with pool open May-Oct)

25 Oct – 1 Nov

€ 234 per night

Guest favourite

Cottage in Flesherton

4.94 out of 5 average rating, 64 reviews

The Golden Getaway

29 Nov – 6 Dec

€ 267 per night

Guest favourite

Cottage in Grey Highlands

5.0 out of 5 average rating, 12 reviews

New build. Cheerful 4 bdrm - Exquisite fall hiking

25 Jun – 2 Jul

€ 332 per night

Guest favourite

Cottage in Markdale

4.83 out of 5 average rating, 12 reviews

Quiet Waterfront Getaway

26 Oct – 2 Nov

€ 183 per night

Guest favourite

Cottage in Chatsworth

4.97 out of 5 average rating, 33 reviews

Luna Log House - forest retreat with outdoor sauna

20–27 Aug

€ 494 per night

Private cottage rentals

Guest favourite

Cottage in Flesherton

4.97 out of 5 average rating, 61 reviews

Modern all-season cottage overlooking Lake Eugenia

16–23 Sep

€ 199 per night

Guest favourite

Cottage in Mulmur

5.0 out of 5 average rating, 43 reviews

The Squire's Cottage

27 Feb – 6 Mar

€ 101 per night

Guest favourite

Cottage in Southgate

4.89 out of 5 average rating, 80 reviews

Thistle And Pine Cottage

5–12 Jan

€ 110 per night

Guest favourite

Cottage in South Bruce Peninsula

5.0 out of 5 average rating, 11 reviews

Sauble River Cottage

29 Nov – 6 Dec

€ 130 per night

Guest favourite

Cottage in Meaford

4.97 out of 5 average rating, 37 reviews

Entire Cottage with Hot Tub, near Beach

24 Sep – 1 Oct

€ 128 per night

Guest favourite

Cottage in Tiny

4.98 out of 5 average rating, 41 reviews

Edmore Cottage at Tiny Beaches

14–21 Sep

€ 187 per night

Cottage in Flesherton

4.83 out of 5 average rating, 12 reviews

Cottage Retreat on 11 Acres

17–24 Aug

€ 214 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

15–22 Nov

€ 354 per night

Quick stats about cottage rentals in Grey Highlands

Total rentals
80 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
80 properties are a good fit for families
Total number of reviews
2.8K reviews
Nightly prices starting at
€ 65 before taxes and fees

Destinations to explore