
Waterfront holiday rentals in Grey Highlands
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Top-rated waterfront rentals in Grey Highlands
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Popular amenities for waterfront rentals in Grey Highlands
Waterfront apartment rentals

PS5 * Pool * Hot Tub * FirePit
The host is very friendly and understandable, and the place is very nice. I will recommend booking this place to everyone.

Stunning 1 Bedroom unit
Just what I was looking for. A peaceful stay close to nature. The train tracks right beside us was powerful. Caused me to stop and take it in. My wife said it was a reminder to stay present in the moment when a train passed. A lot of fun!

Luxury Serene Escape @ Friday Harbour Resort
Friday Harbor was a beautiful location with extremely pretty walking trails. The house felt at home with everything available at your service. Our Airbnb Manager Ana was the sweetest person you could meet. She also gave us a welcome hamper! Definitely recommend to visit this place for a peaceful, home away from home kinda stay :)

Quiet & Pristine Georgian Bay Escape near trails
We had a wonderful stay with Catherine and Tom. The place was spotless and stocked with all the essentials for cooking, making it easy to feel at home. The location was perfect - just a short walk to the town dock and everything else we needed. Catherine and Tom were incredibly flexible and went out of their way to help us during some unexpected situations. They were generous, thoughtful, and always responsive to messages. Their local knowledge was invaluable, and they truly went above and beyond to ensure our comfort. We would highly recommend staying here! 10 out of 10!!

Modern Luxury Delight with a Pool and Hot Tub
Amazing stay, well kept, convenient and comfortable. Joanne is very responsive and flexible.

NEW Luxurious Corner Unit at Friday Harbour Resort
Sandra’s place is just like the pictures super cute, clean and private. The place has everything you need for a great stay. She’s very responsive to messages. It was our 2nd time enjoying her place and we’d look forward to booking with her again!

FH Suite Getaway!
Beautiful place definitely will be returning in the summer friday harbour is a must visit !!

Welcome to waterfront paradise on Georgian Bay
We had a fantastic weekend staying at Gerard’s place! It was just as described from the pics and Gerard provided very clear instructions which made checking in seamless. The place was very clean, spacious, and right on the water! There was also a ton of things to do including kayaking, stand up paddle boarding, board games, a gym with weights as well as a fully stocked kitchen. We had a great time and would definitely come back again in the future!
Waterfront house rentals

Cottage Escape on Lake Eugenia
My family and I stayed at this wonderful cottage for 4 days. It was everything I wanted- cozy, clean, and right on the water. We really enjoyed fishing and sitting outside. The water is really clear and clean. We loved exploring the small towns. The cottage is fully stocked with everything you need for your stay. I am really looking forward to returning in the future!

Island View Cottage
A Perfect Waterfront Getaway: Cozy, Clean, and Family-Friendly with an Exceptional Host! Our stay at this Airbnb was absolutely wonderful! From the moment we arrived, we were struck by the waterfront location, offering serene views and a truly relaxing atmosphere. The home itself was very clean, which is always a top priority, and it was evident that great care is taken to maintain a spotless environment for guests. The helpful host truly made our experience exceptional. Communication was prompt and clear, and they went above and beyond to ensure we had everything we needed, whenever required. This level of hospitality significantly enhanced our stay. The well-equipped kitchen was a dream for preparing meals. It had everything one could possibly need, from essential cookware and utensils to a good range of appliances. We particularly valued how child friendly We highly recommend this place for anyone seeking a clean, comfortable, and welcoming waterfront escape with excellent amen

Heron's Perch
This was our second year at Carrie and Dan's cottage and once again my family and I had a fantastic time. The house is perfectly situated on the river with a nice beach and it has all of the amenities needed. Dan communicated regularly and checked in with us to ensure we had everything we needed. This is a beautiful property which anyone would have fun at.

Luxury Guest House with Private Hot Tub and Trails
We had a lovely stay. The place was even nicer than we expected. This is the best air bnb we’ve ever had. It was really private and really clean, which was exactly what we were looking for. They provided so many little things which just added to the overall experience. Its the small things that go a long way. The place was really open concept and just really well furnished. Gave a fantastic vibe. The hot stub was clean, private and lovely. You wont be disappointed whatsoever here. Thank you for being a fantastic host Rebecca.

Mallory Beach Loft On the Water - Near Bruce Trail
We had an amazing stay at Jane and Steve’s place! They were very warm and were always accommodating and ensuring our stay was going well. Jane even ensured we got to our trail start and end one day. Everything about the “loft” was comfortable, the banana bread was amazing and it felt like we were visiting old friends. Thanks so much for helping to make a rainy cold weekend enjoyable!

Beach House-S/W Exposure! Hot Tub, Sandy Water!
We stayed at Dylan’s place for the weekend with 13 adults and 4 kids. There was enough rooms and beds for all of us with adequate bedding and space. The house was clean and well equipped for our weekend! Before the stay we had lots of questions and Dylan was very responsive and answered everything in a timely manner and with lots of details. He was always following up during the weekend as well. The dock is beautiful and amazing! It was a bit buggy but that’s expected near the waters. We used the kayaks and boat and had a wonderful time!

Happy Valley Ski Golf Spa Relax
A lovely place to stay! Very clean and conveniently located. Would not hesitate to stay here again next time we're in the area!

King Bed Farmhouse- w/ Fire-pit, 75" TV, Ping Pong
Thank you for being a great Host to our group.
Waterfront apartment rentals

2BR Getaway at Friday Harbour All Season Resort
Stephanie was wonderful and the space she has is so perfect! Love that there is main floor back door access and super easy to get in and out of the parking garage as she’s on the main floor. Will definitely stay again!

Friday Harbour Ground Floor w/ Large Terrance
We had amazing time! Tiana goes above and beyond. The outside patio was so nice and relaxing. Recommend to everyone. Thank you!

Stylish getaway condo, resort living
We had a great stay at this stylish comfortable condo in a nice neighbourhood. The condo itself is very clean and has everything,and more,than you need. The brita filter is a big plus ! Comfortable beds, luxurious linnen and a good washer an dryer made us not wanting to leave... Thank you Ron (and Anna)

Designer Condo with beautiful harbour view.
Very beautiful place and surroundings. Host was very helpful with giving us advice and answering any questions we had

Beautiful Condo, 2 Bedrooms and a Den in a Resort!
My kids & I had a fantastic experience at this Airbnb. The space was exactly as described—clean, comfortable, and well-equipped with everything I needed. The host was incredibly responsive and helpful, providing clear check-in instructions and great local recommendations. The location was perfect—close to everything, but quiet enough to relax. I would definitely stay here again and highly recommend it to anyone visiting the area!

Wasaga Beach/WaterFront BeachHouse/ BBQ/AC/parking
We had a wonderful and pleasant stay! The host was very responsive and made sure we had everything we needed. The place was clean, comfortable, and welcoming. We’re already planning to come back again. Highly recommend!

Friday Harbour Luxury Condo Escape, Sleeps 4
My boyfriend and I stayed the weekend, it was a great location, Joe was very responsive and friendly! We had only 1 concern with the bbq that was not clean, but it has been handled with effectively. Overall space was very clean, it was easy to find kitchen supplies, and other items in the house! A great location with stores, restaurants at a walking distance, and other attractions within a 30 minute drive

Marina view at Friday Harbour 2bd/2bth Pool option
Immaculately clean, spacious, and Beautiful condo. It had everything we need and a few steps to the marina. Easy instructions to get inside and parked. I highly recommend!
Quick stats about waterfront rentals in Grey Highlands
Total rentals
100 properties
Nightly prices starting at
₹3,454 before taxes and fees
Total number of reviews
2.6K reviews
Family-friendly rentals
80 properties are a good fit for families
Pet-friendly rentals
50 properties allow pets
Rentals with a pool
30 properties have a pool
Destinations to explore
- Grand River Holiday rentals
- Brampton Holiday rentals
- London Holiday rentals
- Muskoka Lakes Holiday rentals
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- Family-friendly rentals Grey Highlands
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- Blue Mountain Village
- TPC Toronto at Osprey Valley
- Osler Bluff Ski Club
- Horseshoe Resort
- Devil's Glen Country Club
- Beaver Valley Ski Club
- Mount St. Louis Moonstone
- Snow Valley Ski Resort
- Hockley Valley Resort - Golf, Spa and Ski
- Cobble Beach Golf Resort Community
- The Club At Bond Head
- The Georgian Peaks Club
- Caledon Country Club
- Alpine Ski Club
- National Pines Golf Club
- Barrie Country Club
- Inglis Falls
- Craigleith Ski Club
- Legacy Ridge Golf Club
- The Georgian Bay Club
- The Pulpit Club
- Mansfield Ski Club
- Mad River Golf Club
- Shanty Bay Golf Club