Cottage holiday rentals in Grey Highlands
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Grey Highlands
Guests agree: these cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for cottage rentals in Grey Highlands
Cottage rentals with a hot tub
Cottage in Tiny
4.95 out of 5 average rating, 196 reviewsPrivate 40 Acre Cottage with Hot Tub
22–29 May
Cottage in Innisfil
4.91 out of 5 average rating, 128 reviewsStunning Lakefront Cottage Hot Tub & Sauna
30 Nov – 7 Dec
Cottage in Wasaga Beach
4.93 out of 5 average rating, 190 reviewsCharming riverside cottage, walk to beach
7–14 Jan
Cottage in Waubaushene
4.86 out of 5 average rating, 396 reviewsModern Cottage w/ Hot Tub on Trail - Hike/Run
2–9 Jul
Cottage in Innisfil
4.94 out of 5 average rating, 151 reviewsUtopia Villa and Spa
5–12 Jan
Cottage in Innisfil
4.9 out of 5 average rating, 290 reviewsCrystal Beach Cottage & Spa
16–23 May
Cottage in Midland
4.86 out of 5 average rating, 150 reviewsHouse on the Hill, HotTub, Ski, Ice Fish, Trails
19–26 Mar
Cottage in Gravenhurst
4.93 out of 5 average rating, 108 reviewsHOT TUB!The Good Times on Morrison Lake
16–23 Oct
Pet-friendly cottage rentals
Cottage in Wasaga Beach
4.89 out of 5 average rating, 205 reviewsCozy Riverfront Cottage Retreat with Dock / Ski
7–14 Aug
Cottage in Tiny
4.94 out of 5 average rating, 118 reviewsCozy 4 Season Family Cottage
30 Sep – 7 Oct
Cottage in Waubaushene
4.81 out of 5 average rating, 126 reviewsThe Cottage on Coldwater; where bay & trail meet.
8–15 Jun
Cottage in Tiny
4.96 out of 5 average rating, 109 reviewsSummer Getaway - 3 min walk to Beach, Clean & Cozy
10–17 Jun
Cottage in Innisfil
4.83 out of 5 average rating, 241 reviewsCozy cottage nestled in the forest, near the beach
21–28 Jul
Cottage in Flesherton
4.94 out of 5 average rating, 64 reviewsThe Golden Getaway
8–15 Apr
Cottage in Grey Highlands
5.0 out of 5 average rating, 12 reviewsNew build. Cheerful 4 bdrm - Exquisite fall hiking
17–24 May
Cottage in Flesherton
4.97 out of 5 average rating, 64 reviewsSunset Cottage Lake Eugenia Hot Tub 4 Seasons
30 Nov – 7 Dec
Private cottage rentals
Cottage in Lion's Head
4.78 out of 5 average rating, 161 reviewsLookabout Bay Waterview Cottage - The Lakehouse
21–28 Sep
Cottage in Georgina
4.98 out of 5 average rating, 132 reviewsGranny's Cottage
15–22 Oct
Cottage in Flesherton
4.97 out of 5 average rating, 61 reviewsModern all-season cottage overlooking Lake Eugenia
16–23 Sep
Cottage in Flesherton
4.97 out of 5 average rating, 35 reviewsFamily Oasis on Lake Eugenia
11–18 Oct
Cottage in Southgate
4.89 out of 5 average rating, 80 reviewsThistle And Pine Cottage
3–10 Feb
Cottage in Mulmur
5.0 out of 5 average rating, 43 reviewsThe Squire's Cottage
2–9 Mar
Cottage in Southgate
5.0 out of 5 average rating, 20 reviewsLuxurious Creek Retreat With Hot Tub
8–15 Feb
Cottage in Flesherton
4.95 out of 5 average rating, 42 reviewsOutdoor Paradise, Walk to the Lake, Hiking, Biking
22–29 May
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
$94 SGD before taxes and fees
Destinations to explore
- Brampton Holiday rentals
- Muskoka Lakes Holiday rentals
- Kitchener Holiday rentals
- Waterloo Holiday rentals
- Oakville Holiday rentals
- Barrie Holiday rentals
- Tobermory Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Guelph Holiday rentals
- Markham Holiday rentals
- London Holiday rentals
- Mississauga Holiday rentals
- Cottage rentals Canada
- Cottage rentals Ontario
- Rentals with breakfast Grey Highlands
- Family-friendly rentals Grey Highlands
- Rentals with a patio Grey Highlands
- Loft rentals Grey Highlands
- Rentals with lake access Grey Highlands
- Flat rentals Grey Highlands
- Rentals with an EV charger Grey Highlands
- Pet-friendly rentals Grey Highlands
- Ski-in/ski-out rentals Grey Highlands
- Rentals with a sauna Grey Highlands
- Chalet rentals Grey Highlands
- Monthly Rentals Grey Highlands
- Waterfront rentals Grey Highlands
- Rentals with a washing machine and dryer Grey Highlands
- Rentals with a kayak Grey Highlands
- Townhouse rentals Grey Highlands
- Family-friendly rentals Grey Highlands
- Rentals with a hot tub Grey Highlands
- Rentals with a firepit Grey Highlands
- Rentals with beach access Grey Highlands
- Beachfront rentals Grey Highlands
- Apartment rentals Grey Highlands
- Fitness-friendly rentals Grey Highlands
- Rentals with pools Grey Highlands
- Cabin rentals Grey Highlands
- Private suite rentals Grey Highlands
- House rentals Grey Highlands
- Rentals with outdoor seating Grey Highlands
- Rentals with a fireplace Grey Highlands
- Cottage rentals Grey County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom