
Apartment holiday rentals in Grey Highlands
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Top-rated apartment rentals in Grey Highlands
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Weekly apartment rentals

Loft By The Bay
This was my wife and I’s second time visiting Midland to attend the annual butter tart festival. Our previous rental unit last year was great as were the furnishing so the bar was high for this year’s Airbnb rental. In fact, the “Home in Midland” rental unit and the hosts exceeded our expectations. The rental unit's location was only minutes from the festival and most amenities such restaurants, waterfront and stores. We never moved the car during our stay since everything was within a short walk. About the hosts welcoming attitude and hospitality: Upon arrival, we requested an early entry which was granted without hesitation. We were also fortunate enough to meet one of the hosts (Shelby) she was extremely pleasant and assisted us in making sure we were in the right parking spot, which was well indicated. We walked up 2 flights of stairs to get to our unit and were pleasantly surprised at the space of the rental . The pictures online were absolutely on point and matched expectations.

Experience Ski in/Ski out Condo at Blue Mountain!
Me and my four friends had the best time here! It was a perfect ski in ski out, the kitchen had any tool we needed and it was so clean and cozy! Would recommend this place

Treehouse Suite
It’s a great unit, clean, has everything you need and walkable to downtown. Thank you!

Alpine Bliss: King Bed/Pool/HotTub/Shuttle
Very convenient location! The home was spotless, fully equipped and the hosts were very responsive and provided great communication. Would definitely recommend :)

Pond house
Ali was incredibly responsive and helpful throughout our entire stay. He answered all our questions promptly and went above and beyond to ensure we had a comfortable and enjoyable experience. Highly recommended.

The Loft at Bryn Mawr House
⭐️⭐️⭐️⭐️⭐️ One of the Best Airbnb Stays Ever! This was truly one of the best experiences I've ever had with Airbnb. From the moment we walked in, everything felt special — the apartment was beautifully designed, warm, and welcoming, with softly lit scented candles already creating a cozy atmosphere. We were also greeted with thoughtful touches like a complimentary bottle of wine, cookies, and yogurts for breakfast — such a kind and generous gesture! The place itself is quiet and peaceful, and enjoying morning coffee by the little lake with the fish was simply magical. This stay made our weekend unforgettable. Huge thanks to Adele, our wonderful host — your hospitality and attention to detail were incredible. I wish you continued success with your business, and I’d return in a heartbeat. Hands down, the best Airbnb experience I’ve ever had! 💫

Lovely 1 bedroom apartment in Harriston
I would highly recommend it. It's super cute and also close to restaurants and shops which I am sure would be helpful for extended stays

Private with Self Check-in Bright & Modern Comfort
We really appreciated all the big and little things arranged in this Airbnb for us: modern appliances (the washer-dryer were particularly awesome), a well-stocked kitchen (loved the little milk and cream cartons in the fridge), clean bathroom, extra USB plug points and cables, fun board games and Amazon prime available on the TV. The unit was clean and comfy and we had a great time!
Private apartment rentals

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 Cottage - The Pine Loft
Hands down the best Airbnb we’ve ever stayed in After almost three years of Airbnbs around the world, this one in Canada tops them all. We stayed in both the Lookout (the little house) and the Pine Lodge (above the store)—and didn’t want to leave. The Lookout felt like a cozy sanctuary: garden, sauna, spotless, fully equipped. The Pine Lodge had a steam room (huge bonus!), comfy couches, a big dining table, and a fire always going. But what made it truly special were Krystal and Madison—the kindest, most caring hosts we’ve ever had. It felt like arriving at friends’, not strangers’. During a freak ice storm, they moved us to a backup-powered house and even brought us food. Just wow. Local tips: • Cawaja Store: best coffee, insane ice cream, and local broths, pies, soups. • Mums Restaurant: old-school diner, fresh, cooked-to-order food. • The Friendly Corner: lovely for sunny outdoor meals.

Oro-medonte/in/out pool/ski-2
Nice property, great location, Huong is a very responsive

Double Waterside Beach Oasis
love the location, very cozy felt at home. lots of amenities. Love the rain showers. washer and dryer a plus

Guest Suite in Hockley Valley
This was one of the most beautiful places I've ever stayed! I attended a wedding in the area and my only wish is that I had more time on the property. I would recommend this place to anyone and I hope I can stay again.

Bright Main floor in Barrie With parking&Amenities
Enjoyed my stay Jomana was wonderful and hosted me well she is flexible and nice

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!

By The Bay spacious one bedroom
Staying at Mine and Karen‘s place has been nothing short of amazing. The apartment is located in a peaceful setting and feels brand new, making you feel at home instantly. The host has been extremely accommodating and communicative as well. Thanks again for everything! So if you’re in the area, don’t hesitate!
Apartment rentals with a hot tub

Oasis of luxury: 1 bdrm retreat w/Hot Tub Access
Great place! Very clean and comfortable home. In a great location as well. The hosts were very accommodating and helpful.

Charming and Luxurious 2BR+1Bath Guest Suite
We celebrated my daughter’s birthday at Ilyia’s place. She was very responsive and really tried to accommodate all our requests. The basement is spacious and the kitchen is lovely. I also really appreciate the painting that she made for our daughter. Thank you Ilyia! Few things I would comment is that the hot tub isn’t very clean. Lotss of dirt and leaves floating which we cleaned before use but we also found a bunch of hair at the bottom of the tub. The backyard chairs and table also need some cleaning. The bedsheets and blankets smelled musty/old which I don’t mind but my kids tend to smell everything and a bit bothered. However overall, we had a fun birthday weekend and I still give it a 5 star. Perfect for small event/gathering. Thanks again Ilyia and Larissa!

Gym+Pool+PetFriendly+KingBeds
Sean is very Friendly and Professional. He responds to messages quickly. He is an amazing host where he is checking in on us ensuring if we needed anything he is only a phone call away. We have been going to the Resort for years. Easy to get too, very peaceful and the Units are so simple but nice. Not many places take pets but Sean's does which helped us alot. The beds are super comfortable, probably the best sleep I have had in a long time. Kitchen was equipped with everything we needed for our Stay. The Kids loved the gym to work out and then we spend quite a few hours at the pool. The fire pit was nice to sit at especially with the chilly weekend we just had. We will be back for sure to be Sean's Guest.

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!

Modern Condo at Friday harbour/Pet Friendly
We had a great stay! The place was spotless, the check-in process was super easy, and the location was perfect—just a short walk to the harbour. The host was very responsive and made sure everything went smoothly. We would definitely stay here again!

Beautiful 2 Bed/2 Bath Condo, Private Balcony
This was our second time staying at Julie’s place and it was great! Will definitely be going back.

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

Spacious Hideaway in Nature
We had a wonderful stay at Elijah's! It was clean, peaceful and relaxing and we absolutely loved the amenities! We will definitely be coming back : )
Quick stats about flat rentals in Grey Highlands
Total rentals
80 properties
Nightly prices starting at
$51 SGD before taxes and fees
Total number of reviews
6.6K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
40 properties have a pool
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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
- The Nest Golf Club