Cottage holiday rentals in Grey Highlands

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Popular amenities for cottage rentals in Grey Highlands

Cottage rentals with a hot tub

Guest favourite
Cottage in Bracebridge
4.93 out of 5 average rating, 105 reviews

Waterfront cottage on quiet Spence lake

SarahRating, 5 stars2 months ago
This is a beautiful place to stay, right on the lake with an amazing view, and a friendly beaver right next door! Our highlights were the hot tub, the fire pit and kayaking on the lake. This spot would be amazing in the Summer. The house is clean and well set up, the 2 downstairs bedrooms are small but just fine for sleeping. There is plenty of room in the rest of the house.
Top guest favourite
Cottage in Severn Bridge
5 out of 5 average rating, 151 reviews

CozyPeaceful LakeCottage HotTub Canada

LizhanRating, 5 stars5 days ago
Our family enjoyed a nice, quiet stay at Sarah’s place. The view is beautiful, living space is spacious and comfortable, with good wifi, and fishing at the dock is a great way to enjoy some relaxed time. Sarah is very responsive for questions, which we thoroughly appreciate.
Top guest favourite
Cottage in Brechin
4.98 out of 5 average rating, 126 reviews

Nordic Spa- Sauna: Spring Getaway

StevenRating, 5 stars3 days ago
Amazing time at this wonderful cottage. The hosts were very responsive and friendly, and have put a lot of time and energy into making this cottage an excellent stay. The hosts for this cottage clearly have a passion for making people feel right at home. Thoughtfully, they've left notes, instructions, videos, and even created home automations to make staying here as easy as possible. Everything was fully stocked from cutlery, spices, cleaning supplies, linens, etc. there was almost nothing that they missed out on that a group of people might need! The Hot tub and Suna were wonderful additions that we took full advantage of. The bed rooms and guest houses were cozy and comfortable (with AC/heating). The waters were very nice. Sandy lake that doesn't get too deep until much much further out. The dock was well constructed and great for relaxing. Overall, one of the best AirBnB cottages that we've stayed at in years.
Superhost
Cottage in Waubaushene
4.86 out of 5 average rating, 477 reviews

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

HayleyRating, 5 stars6 days ago
Stayed here our first time using air bnb. The place was beautiful and was exactly what the website said it would be. Felt very comfortable and at peace. I highly recommend this place!
Guest favourite
Cottage in The Blue Mountains
4.91 out of 5 average rating, 148 reviews

Luxury Chalet in Blue Mountains with HotTub Sauna

DanielRating, 5 stars1 week ago
We had an amazing time! The atmosphere was immaculate and the vibes were perfect! Host Jakub was extremely helpful and friendly! Would go back again!
Guest favourite
Cottage in Innisfil
4.9 out of 5 average rating, 218 reviews

Utopia Villa and Spa

Syed,Qumber RazaRating, 5 stars1 week ago
We had a wonderful stay at Shahrzad’s cottage in Innisfil! The place was cozy, clean, and exactly as described. It had everything we needed for a relaxing getaway. Shahrzad was a fantastic host—very responsive and thoughtful. The location was peaceful and close to the lake, which made it perfect for a weekend escape. We would definitely stay here again. Highly recommended!
Superhost
Cottage in Innisfil
4.88 out of 5 average rating, 179 reviews

Stunning Lakefront Cottage Hot Tub & Sauna

PetroRating, 5 stars1 week ago
Fantastic place and beautifull view. Kris was very accommodating and very helpful. The amenities made the stay worth every penny. would definitely stay again.
Superhost
Cottage in Owen Sound
4.76 out of 5 average rating, 203 reviews

Balmy Breezes - Waterfront Cottage with Hot Tub

ErynRating, 5 stars1 week ago
We had a wonderful time in Steve and Jane's quaint and cozy cottage! The beautiful view and the sound of the water made our time spent there enjoyable and peaceful. The cottage was clean, instructions were clear and they had everything you might need to make your stay a wonderful one. Steve and Jane were also quick to respond to any questions we had prior to and during our stay. Amazing hosts!! Thank you for a great time!

Pet-friendly cottage rentals

Guest favourite
Cottage in Bracebridge
4.92 out of 5 average rating, 206 reviews

Charming cottage on Lake Muskoka

SugeethRating, 5 stars1 week ago
We had a wonderful time here on a short excursion out of the city! the cottage itself is magical with a beautiful view of the lake and a gorgeous back patio shaded by trees. Bryan and Pam were very helpful and had made sure to provide everything we needed and more
Guest favourite
Cottage in Victoria Harbour
4.81 out of 5 average rating, 199 reviews

Serenity, Simplicity and Stone

AshleyRating, 5 stars3 days ago
We had a wonderful stay at Carol's place. the cottage is beautiful, cozy and clean. It had all the amenities we needed. The area is very quiet and peaceful, which was exactly what we were looking for. The walking trails are beautiful. We brought our kayaks and went to a public beach/boat launch which was only a two minute drive away. Couldn't have been happier with everything. We would love to return for another getaway.
Guest favourite
Cottage in Bala
4.96 out of 5 average rating, 209 reviews

Lakefront Cottage with Sauna and Steam Room

SubathiraRating, 5 stars2 weeks ago
We loved this place. From start to finish it was fantastic. Great location. Open and spacious. Everything we needed was provided. The host was very responsive and gave good clear instructions. We had a fantastic time to wind down.
Guest favourite
Cottage in Tiny
4.95 out of 5 average rating, 153 reviews

Cozy 4 Season Family Cottage

SamanthaRating, 5 stars1 week ago
Great cottage in a perfect location, just a short walk to the water Very clean, with a spacious yard and thoughtful touches like provided firewood and essentials. Would definitely stay again!
Superhost
Cottage in Gravenhurst
4.92 out of 5 average rating, 154 reviews

Waterfront @Muskoka Pines /kayaks/bbq/firepit

AmishaRating, 5 stars3 weeks ago
Very accommodative and responsive host. The place is at a great location. It is breathtaking and peaceful.
Guest favourite
Cottage in Barrie
4.71 out of 5 average rating, 331 reviews

The Guesthouse on the North Shore Trail

cindyRating, 5 stars3 days ago
My girlfriend and I stayed at Don’s place Saturday night with our two dogs, and it was perfect for us….having the waterfront trail right behind it was even better…..it was relaxing and very quiet and just like shown in the pictures! We would highly recommend it! Thank goodness for the air conditioning with this heat wave!
Superhost
Cottage in Georgina
4.87 out of 5 average rating, 144 reviews

Waterfront Cottage-Sauna, Dock, 4-bed, 4 Parking

Hok YinRating, 5 stars3 weeks ago
My friends and I had a truly fabulous cottage experience here! The washrooms were clean and tidy, which made our stay extra comfortable. We also appreciated the entertainment options available. Even though the weather was a bit cool and the dock slightly tricky to manage, we had an amazing time using the kayaks for the first time! The host provided life jackets, which made our water adventures both safe and memorable. Another highlight was the sauna — such a relaxing and refreshing treat after a day of outdoor activities. It was our first time trying a sauna, and it was easy to use. We loved it! One more thing worth mentioning — one of my friends accidentally left her phone behind. The host and cleaning team acted quickly and efficiently, and the phone was returned the next day! Overall, we would absolutely choose this cottage again. The great location, cleanliness, well-prepared facilities, and the kind and thoughtful host made this a wonderful getaway. Highly recommended!
Guest favourite
Cottage in Tiny
4.97 out of 5 average rating, 120 reviews

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

JuliaRating, 5 stars3 months ago
We had a wonderful winter getaway at Woodward by the Beach! The home was beautiful and far exceeded our expectations. It was clean, nicely decorated, and well stocked with the essentials. We especially loved the fire! The host, Kevin, was extremely responsive and even took the time to provide us with recommendations for snow tubing, tobogganing, restaurants, and cafes. The home is in a great location and there are no shortage of activities, restaurants, and shops within short driving distance. We can’t wait to come back in the summer! Thank you Kevin!

Private cottage rentals

Top guest favourite
Cottage in Flesherton
5 out of 5 average rating, 52 reviews

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

JulianRating, 5 stars3 weeks ago
Jennifer’s place is everything you want for your stay- The home is very private, clean and has lots to do at the location. Jennifer is incredibly responsive, friendly and beyond helpful. We look forward to coming back as my family knows at Jennifer’s location we will never be disappointed. Thank you for everything!
Superhost
Cottage in Flesherton
4.69 out of 5 average rating, 49 reviews

Cozy 3 Bedroom Cottage Retreat

SaraRating, 5 stars8 months ago
Our second stay at Sydney's cottage was great! Sydney was very responsive to any questions and we enjoyed our stay. It is a good mix of rustic cottage but with everything you need to be comfortable and relaxing. It's right on the main road but the trees out front help it feel more secluded. With beautiful fall trees around the yard's pond and a quick walk to the lake to enjoy the view it was a lovely fall getaway.
Guest favourite
Cottage in Kimberley
4.91 out of 5 average rating, 88 reviews

Ideal Summer Getaway- BBQ, Hot Tub, Sauna, Firepit

SierraRating, 5 stars1 week ago
Jovita & Julio were excellent hosts from the very beginning! The listing provided all the information I could need and they were great about communication. The cottage was perfect for what my group needed - the kitchen was fully stocked and we never felt like we were missing anything, including activities. I would recommend this place to any groups looking to spend quality time together in nature. Thank you again Jovita & Julio - your cottage and your hospitality made this trip unforgettable!!
Guest favourite
Cottage in Meaford
4.98 out of 5 average rating, 86 reviews

Bayview Oasis: Luxe Lakeside Escape w/ Pickleball

RyanRating, 5 stars1 week ago
Amazing home with so much to offer for outdoor activities! Even a pool table inside that was great for a rain day and pizza oven is covered by a pavilion which was great too we made pizzas every day! Hot tub is a great option too but the only negative part of the whole experience was that the hot tub was quite dirty. We messaged the host who was very responsive and had someone come out to clean it but it needs a little more maintenance to be cleaned properly. Other than that 10/10 stay would definitely go back!
Superhost
Cottage in Creemore
4.76 out of 5 average rating, 426 reviews

Cottage on the Noisy River/Blue Mountain/Wasaga

AlyssaRating, 5 stars2 weeks ago
Nikki’s family cottage is truly a gem outside of the city. I stayed in her property for a quick 3 day solo R&R with my dog. This was the perfect property for my dog to play around and let out his zoomies. Also, there were so many spots in the property to lounge around with my glass of wine in hand. The river was perfectly shallow for me to walk on the rocks, with my water shoes, ofcourse. The cottage was clean and cozy, the kitchen is stocked with all your needs and they’ve got plenty of throwback DVD movies to choose from. Nikki’s house manual and rules were very clear and easy to follow. She was also quick to reply back when needed, leaving me not to worry. I’ll definitely be back! Thanks Nikki + Family!
Superhost
Cottage in Flesherton
4.81 out of 5 average rating, 21 reviews

Cottage Retreat on 11 Acres

RachelRating, 5 stars4 months ago
We loved our stay. Sara was very responsive and helpful. The home was cozy, clean and comfortable. The snow was more than 3 feet deep when we arrived and it snowed everyday we were there! The property was a magical winter-wonderland that we explored with snowshoes. The driveway in was plowed so we had no difficulties getting in and out and, despite feeling so private, it was just a short drive to an amazing bakery and other great amenities. We would definitely return!
Top guest favourite
Cottage in Mulmur
5 out of 5 average rating, 85 reviews

The Squire's Cottage

JonathanRating, 5 stars1 week ago
Best place ever to start a honeymoon. We arrived around 11:30 pm and the cottage was unlocked and ready to go. Everything was cozy and homey. Jan gave us an amazing cheese and fruit board and Doug had fresh baked cookies for us. Peaceful location to unwind. Wi-Fi was a bit spotty but that’s probably the location (and helps force an unplug). The piano was a great extra touch!
Superhost
Cottage in Meaford
4.74 out of 5 average rating, 496 reviews

The Surf Shack - Hot Tub, Bay Views & Beach Access

VisobhRating, 5 stars6 days ago
What a perfect location for our family getaway! The place was great to accommodate all of us. The amenities were great. We made the best of the fire pit and BBQ. To add it was nice and close to BLUE MOUNTAIN

Quick stats about cottage rentals in Grey Highlands

  • Total rentals

    80 properties

  • Nightly prices starting at

    ₹4,300 before taxes and fees

  • Total number of reviews

    3K 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