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Cottage holiday rentals in Grey Highlands

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Popular amenities for Grey Highlands cottage rentals

Cottage rentals with a hot tub

Superhost

Cottage in Kimberley

4.85 out of 5 average rating, 332 reviews

A Cozy Country Retreat *Indoor Hot Tub* Ski* Wi-Fi

NikaRating, 5 stars1 month ago
We had a relaxing and fun trip! David really created a whole experience and we enjoyed all the games and amenities they provided for us. We would definitely come back again!
Guest favourite

Cottage in Tiny

4.96 out of 5 average rating, 225 reviews

Private 40 Acre Cottage with Hot Tub

AntonioRating, 5 stars1 month ago
was great had a good time with my wife it was peaceful and private
Guest favourite

Cottage in Severn Bridge

5 out of 5 average rating, 115 reviews

CozyPeaceful LakeCottage HotTub CheckOutOurReviews

KaterinaRating, 5 stars4 days ago
We had an incredible stay at Stu and Sarah's! They came to greet us when we arrived, even though it was late, and showed us how everything worked. They were super responsive anytime we had a question. The place was quiet and peaceful, in a beautiful rural surrounding. We loved the woodstove and hottub! The kitchen is incredibly well-equipped, beds were very comfortable, and ample linens were provided. Sarah and Stu sent a detailed guide to the cottage and the area, and graciously allowed us to stay late on check-out day due to bad driving conditions. We will be rebooking with them in summer to see the landscape in another season and enjoy the lake!
Superhost

Cottage in Waubaushene

4.86 out of 5 average rating, 447 reviews

Charlie the Cottage | Hot Tub | Trail | Hike/Run

LaurieRating, 5 stars4 weeks ago
We had a great time!! It would have been nice to have a greater variety of cookware since there was only one huge pot available. Also basic condiments such as ketchup were missing from the fridge which is often provided by most hosts. However the place the super cute and clean.
Guest favourite

Cottage in Gravenhurst

4.97 out of 5 average rating, 200 reviews

Muskoka Oasis: Hot Tub, Sauna & Nature Retreat

VolodymyrRating, 5 stars4 days ago
great location, nice and cozy house.
Guest favourite

Cottage in Port Severn

4.94 out of 5 average rating, 136 reviews

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

RachelRating, 5 stars2 months ago
This beautiful cottage has room for the entire family to enjoy while still having enough rooms or outdoor spaces for family members to enjoy their own quiet time as well. The lake is beautiful and we look forward to going back in the summer!
Guest favourite

Cottage in Innisfil

4.89 out of 5 average rating, 161 reviews

Stunning Lakefront Cottage Hot Tub & Sauna

MichelleRating, 5 stars1 month ago
My family enjoyed the stay at Kris’ cottage. We made sure to take advantage of the hot tub and sauna. It was so serene. Kris accommodated a late check out on Christmas Day, which we greatly appreciated. It was nice to be able to take our time to pack up and not rush on Christmas Day. The house is well maintained. We cooked a few meals in the kitchen. There was basic utensils and cooking supplies, so if you’re cooking a feast, you may need to bring your own cooking ingredients (ie. oil and spices) as described in the listing as well as measuring cups. The cottage was cozy, enough room for the 5 of us. I loved getting up to the view of the backyard and lake every day. The large backyard windows brought in plenty of sunlight into the family room. Upstairs had 2 bedrooms. The ceiling of the bedrooms were slanted, probably the shape of the roof, which made it a little small. The bedroom ensuite was tiny, but functional. Overall, a great last minute Christmas getaway for my family!
Superhost

Cottage in Orillia

4.87 out of 5 average rating, 103 reviews

FRIEND LAKE HOUSE

ShaghayeghRating, 5 stars1 month ago
Highly recommend this place , so peaceful, easy access, modern and clean , host was so responsive and easy to communicate

Pet-friendly cottage rentals

Guest favourite

Cottage in Meaford

4.95 out of 5 average rating, 93 reviews

Woodski Winter Haven: Mountain Cottage Near Skiing

VeronicaRating, 5 stars1 week ago
We were so lucky to find this place available!! The property is very well maintained, it is very spacious and comfortable! Super fully equipped with everything that you need and more. We were very happy with our stay and with how attentive and responsive the host was. We highly recommend this place!
Superhost

Cottage in Flesherton

4.95 out of 5 average rating, 38 reviews

Four Season Waterfront Cottage on Lake Eugenia

SoleRating, 5 stars5 months ago
Our family had a fantastic vacation at Paula and Chris’s cottage on Lake Eugenia. This beautifully rustic and well-loved cottage is perfectly equipped for guests of all ages and interests. Although the weather started off cold and rainy, and not good for swimming at first, we took the opportunity to explore the nearby Bruce Trails, just a short 5-10 minute drive away, where we enjoyed spectacular views. Back at the cottage, the fire pit made our evenings cozy and memorable, and the hot tub was an amazing bonus while we waited for the weather to improve. Once the sun came out, the kids couldn’t wait to jump into the lake, and they had an absolute blast! The Lily pad was amazing- hours and hours of uninterrupted fun. Lake Eugenia is a stunning spot perfect for swimming and just the right size for exploring by canoe or kayak. A big thank you to Chris and Paula for being such wonderful hosts!
Superhost

Cottage in Tiny

4.94 out of 5 average rating, 142 reviews

Cozy 4 Season Family Cottage

HardikkumarRating, 5 stars3 months ago
Well, we loved the place. The cottage looks much better than it is in the pictures. We enjoyed inside, surrounding and fire pit. Anthony was very responsive and he let us stayed 1:30 hours extra on the checkout day which was extremely nice. Hoping to visit again in the summer 2025.
Guest favourite

Cottage in Gravenhurst

4.88 out of 5 average rating, 118 reviews

Waterfront 3 BR Cottage 4 Seasons Gravenhurst Heat

CassandraRating, 5 stars4 weeks ago
Stayed for a few nights over the holidays. Jonathan was very responsive and had above and beyond instructions and details for all the airbnb and area had to offer! Very cozy at home feeling and was so accommodating to us! would definitely return for a Muskoka get away!
Guest favourite

Cottage in Meaford

4.94 out of 5 average rating, 51 reviews

Charming 3bdrm cottage on Georgian Bay!

MontgomeryRating, 5 stars4 months ago
Very enjoyable stay. Beautiful cottage. Excellent host. We would definitely stay here again.
Superhost

Cottage in Sauble Beach

4.72 out of 5 average rating, 72 reviews

My Blue Haven - Sauble Beach, Ontario

CindyRating, 5 stars5 months ago
The cottage looked like the photos, was super clean and very comfy. We loved all the different outdoor seating options. There was a bird feeder in the tree and we enjoyed watching the blue jays and gackles. The beach was about a 10 minute walk. We forgot our marshmallow skewers, but they had some. The kitchen was well equipped. We would stay here again.
Guest favourite

Cottage in Tiny

4.87 out of 5 average rating, 39 reviews

Balm Beach Cottage: Hot Tub/GameRoom/more!

FernandaRating, 5 stars3 weeks ago
Justin is an excellent host. Always kind and respond pretty fast! The house is in a great place, with many walkable things to do.
Guest favourite

Cottage in Sauble Beach

4.93 out of 5 average rating, 28 reviews

Sauble Beach - Quiet 4 Season Cottage Near Beach

LauraRating, 5 stars1 month ago
Had a great, last-minute wintry stay at Jill’s. The fireplace kept everyone cozy, and there was lots for our kiddo to keep occupied.

Private cottage rentals

Guest favourite

Cottage in Wasaga Beach

4.86 out of 5 average rating, 22 reviews

The River's Edge - Cottage 1: The Riverbank House

VaniaRating, 5 stars1 month ago
Fantastic getaway, close to food and other necessities Lots of room inside Comfortable and cozy
Guest favourite

Cottage in Howdenvale

4.89 out of 5 average rating, 44 reviews

Beautiful Private Cottage on 10 Acres and a view!

RavenRating, 5 stars3 months ago
We had an amazing stay! It was our second time staying and everything was perfect. It’s a cozy cottage with an at-home feel. Set the pilot light in the gas fireplace for us and let me know in advance, and offered to come pick up chairs after a windstorm the night before our stay. Very lovely host with a very speedy response time and a wonderful property!
Guest favourite

Cottage in Southgate

4.89 out of 5 average rating, 104 reviews

Thistle And Pine Cottage

AmberlynnRating, 5 stars2 weeks ago
Jaclyn's place is exactly what I needed. The place is private, serene, and felt so homey. It was a lovely break from he city. Will visit again. Thank you for hosting us.
Guest favourite

Cottage in Coldwater

4.97 out of 5 average rating, 38 reviews

Charming 3BR Cottage on Tranquil Lake 🐦🛶🎣🏊‍♀️

KaiRating, 5 stars5 months ago
My group and I had an excellent stay at the cottage. The lake is beautiful and the property is as well; inside and out. The location is quiet, yet not too secluded, making the overall experience very peaceful. The home was also very clean, functional, and had even more amenities than we were even expecting! Definitely would visit again. Thanks Jenny and Bob!
Guest favourite

Cottage in Tiny

4.97 out of 5 average rating, 36 reviews

2 Bedroom Plus Bunkie Woodland Beach Cottage

JenRating, 5 stars3 months ago
Our family had an enjoyable Thanksgiving weekend at Carol's property. The cabin was cozy and charming, the bunkie was super cute and the deck and fire pit were amazing spots to hang out at. It's a short walk to the water and a convenience store/lcbo. Our only issue was that we didn't stay long enough!
Superhost

Cottage in Sauble Beach

4.88 out of 5 average rating, 26 reviews

Sauble Beach Front Cottage 2

JoanneRating, 5 stars29 months ago
My sister and I had a wonderful week! The cabin is clean, well-appointed and surprisingly close to the beach. Labour Day Weekend was busy but everyone was friendly and respectful, and everyone abided by the the 11pm quiet rule. This cabin is ideally located. It is a 20 minute walk / 5 minute drive to the Sauble Beach strip and the town of Sauble Beach is a great take-off point for a wide variety of day trips, shops and restaurants in Southhampton, Port Elgin, Owen Sound, Tobermory. The sunsets and the gorgeous blue-green water will knock you out. If you have any beach-bum in you, this is the place for you.
Guest favourite

Cottage in Palgrave

4.99 out of 5 average rating, 207 reviews

Hockley valley, up country guest cottage

ChristineRating, 5 stars2 months ago
Fere and her family were fantastic, and the location is a beautiful sanctuary. Looking forward to connecting again soon. Merci!💓🕊✨
Superhost

Cottage in Kemble

4.82 out of 5 average rating, 139 reviews

Georgian Bay Waterfront Oasis

DanRating, 5 stars1 month ago
A peaceful and cozy escape for long it short. Recommend arriving during daylight hours.

Quick stats about cottage rentals in Grey Highlands

  • Total rentals

    80 properties

  • Nightly prices starting at

    $80 AUD 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

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Grey County
  5. Grey Highlands
  6. Cottage rentals