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Cottage vacation 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.

Nov 18 – 25

ﺩ.ﺇ829 per night

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.

Jul 24 – 31

ﺩ.ﺇ518 per night

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.

Nov 28 – Dec 5

ﺩ.ﺇ1,587 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.

Jun 7 – 14

ﺩ.ﺇ458 per night

Cottage in Lion's Head

4.9 out of 5 average rating, 112 reviews

Myles Bay Cottage

Beautiful, quiet, private setting steps from the water and gorgeous sandy beach. Cottage is located near Lions Head ON on Myles/Stokes Bay. Boat launch close by (free government dock) one concession south, Lions Head Marina on east side of peninsula, or gradual entry steps away is good for canoe, kayak, or jet ski entry. Nicely finished interior for all your vacation needs. Available for full weeks, Sat-Sat, July & August (check in/out day is Saturday). STA Permit: NBP-2021-425

Oct 24 – 31

ﺩ.ﺇ468 per night

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

Aug 1 – 8

ﺩ.ﺇ2,091 per night

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.

Mar 2 – 9

ﺩ.ﺇ642 per night

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.

Dec 2 – 9

ﺩ.ﺇ1,200 per night

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

Jan 5 – 12

ﺩ.ﺇ420 per night

Cottage in Torrance

4.97 out of 5 average rating, 195 reviews

Beautiful Nine Mile Lake

Beautiful Muskoka getaway! Newly renovated 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.

May 20 – 25

ﺩ.ﺇ627 per night

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

Apr 13 – 20

ﺩ.ﺇ668 per night

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.

Jan 22 – 29

ﺩ.ﺇ860 per night

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

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 Grey Highlands cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Tiny

4.95 out of 5 average rating, 196 reviews

Private 40 Acre Cottage with Hot Tub

May 22 – 29

ﺩ.ﺇ923 per night

Cottage in Innisfil

4.91 out of 5 average rating, 128 reviews

Stunning Lakefront Cottage Hot Tub & Sauna

Nov 30 – Dec 7

ﺩ.ﺇ1,411 per night

Cottage in Wasaga Beach

4.93 out of 5 average rating, 190 reviews

Charming riverside cottage, walk to beach

Jan 7 – 14

ﺩ.ﺇ1,410 per night

Cottage in Waubaushene

4.86 out of 5 average rating, 396 reviews

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

Jul 2 – 9

ﺩ.ﺇ1,650 per night

Cottage in Innisfil

4.94 out of 5 average rating, 151 reviews

Utopia Villa and Spa

Jan 5 – 12

ﺩ.ﺇ982 per night

Cottage in Innisfil

4.9 out of 5 average rating, 290 reviews

Crystal Beach Cottage & Spa

May 16 – 23

ﺩ.ﺇ1,031 per night

Cottage in Midland

4.86 out of 5 average rating, 150 reviews

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

Mar 19 – 26

ﺩ.ﺇ804 per night

Cottage in Gravenhurst

4.93 out of 5 average rating, 108 reviews

HOT TUB！The Good Times on Morrison Lake

Oct 16 – 23

ﺩ.ﺇ1,681 per night

Pet-friendly cottage rentals

Cottage in Wasaga Beach

4.89 out of 5 average rating, 205 reviews

Cozy Riverfront Cottage Retreat with Dock / Ski

Aug 7 – 14

ﺩ.ﺇ1,388 per night

Cottage in Tiny

4.94 out of 5 average rating, 118 reviews

Cozy 4 Season Family Cottage

Sep 30 – Oct 7

ﺩ.ﺇ621 per night

Cottage in Waubaushene

4.81 out of 5 average rating, 126 reviews

The Cottage on Coldwater; where bay & trail meet.

Jun 8 – 15

ﺩ.ﺇ564 per night

Cottage in Tiny

4.96 out of 5 average rating, 109 reviews

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

Jun 10 – 17

ﺩ.ﺇ1,132 per night

Cottage in Innisfil

4.83 out of 5 average rating, 241 reviews

Cozy cottage nestled in the forest, near the beach

Jul 21 – 28

ﺩ.ﺇ642 per night

Cottage in Flesherton

4.94 out of 5 average rating, 64 reviews

The Golden Getaway

Apr 8 – 15

ﺩ.ﺇ905 per night

Cottage in Grey Highlands

5.0 out of 5 average rating, 12 reviews

New build. Cheerful 4 bdrm - Exquisite fall hiking

May 17 – 24

ﺩ.ﺇ1,136 per night

Cottage in Flesherton

4.97 out of 5 average rating, 64 reviews

Sunset Cottage Lake Eugenia Hot Tub 4 Seasons

Nov 30 – Dec 7

ﺩ.ﺇ1,259 per night

Private cottage rentals

Cottage in Lion's Head

4.78 out of 5 average rating, 161 reviews

Lookabout Bay Waterview Cottage - The Lakehouse

Sep 21 – 28

ﺩ.ﺇ647 per night

Cottage in Georgina

4.98 out of 5 average rating, 132 reviews

Granny's Cottage

Oct 15 – 22

ﺩ.ﺇ633 per night

Cottage in Flesherton

4.97 out of 5 average rating, 61 reviews

Modern all-season cottage overlooking Lake Eugenia

Sep 16 – 23

ﺩ.ﺇ754 per night

Cottage in Flesherton

4.97 out of 5 average rating, 35 reviews

Family Oasis on Lake Eugenia

Oct 11 – 18

ﺩ.ﺇ1,369 per night

Cottage in Southgate

4.89 out of 5 average rating, 80 reviews

Thistle And Pine Cottage

Feb 3 – 10

ﺩ.ﺇ441 per night

Cottage in Mulmur

5.0 out of 5 average rating, 43 reviews

The Squire's Cottage

Mar 2 – 9

ﺩ.ﺇ328 per night

Cottage in Southgate

5.0 out of 5 average rating, 20 reviews

Luxurious Creek Retreat With Hot Tub

Feb 8 – 15

ﺩ.ﺇ864 per night

Cottage in Flesherton

4.95 out of 5 average rating, 42 reviews

Outdoor Paradise, Walk to the Lake, Hiking, Biking

May 22 – 29

ﺩ.ﺇ1,138 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
ﺩ.ﺇ257 before taxes and fees

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