
Vacation rentals with outdoor seating in Grey Highlands
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Top-rated outdoor seating rentals in Grey Highlands
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Popular amenities for Grey Highlands outdoor seating rentals
House rentals with outdoor seating

20 min from Blue Mountain -Relax & Enjoy Winter
Such a great place to stay after skiing at Blue Mountain! Definitely recommend.

Debonair Luxury Stays
Long weekend with family here. Was perfect. Thank you. Exactly as advertised. Clean and very functional for us. Highly recommended.

Porchside Retreat: Sauna and Treeline Backyard
**Title: A Wonderful Stay at a Charming Cottage** Our stay was absolutely fantastic! Christine and Kylie were a delight to deal with—friendly, proactive, and always reachable, they promptly answered all our queries. Every interaction with them was a pleasure! The cottage is exactly as described; everything functioned perfectly, and the setting is simply beautiful. The pet-friendly aspect was a lovely bonus. We found this property to be charming and cannot recommend it highly enough. We will definitely be returning, as it’s perfectly located for our needs. Thank you, Christine and Kylie, for such a memorable experience!

kids paradise, extra storage, fenced, pet friendly
We loved staying here! There was SO much space, it felt very homey and cozy. The backyard was beautiful! This is an amazing home to stay in with tons and tons of room.

Charming 3 bed house, your gateway to Georgian Bay
The place was very clean and the location it’s amazing, you are close to a lot of trails and to Blue Mountain Village. Jennifer and Keith were very responsive and friendly. It was a great experience!

Simple Downtown Comfort
Really lovely place -- three comfortable bedrooms, great sitting and dining area, nice kitchen. Great hosting touches -- extra towels, easy to get onto WiFi, chocolates left for the guest, responsive host. Beautifully decorated in antique-looking solid wood furniture, nice pictures and miscellaneous cute items. Might be tricky for anyone with mobility issues as the bathroom is on the main floor and bedrooms are up an old uneven staircase -- one of us was a person who goes to the bathroom a few times a night and that wasn't ideal for her. For me, it was perfect.

Dreamy Place in Midland
Farhad is a nice host. Feels like home experience. ♥️

Walkout basement & ravine view (Short/Mid Term)
My stay at Paris' place was fantastic. During my stay there was an ice storm and Paris made sure that we knew where the flashlights were and extra blankets to make sure we would be good if we lost power. I felt right at home as they thought of everything right down to the bottles of water.
Apartment rentals with outdoor seating

Beautiful Riverside Country Apartment
Excellent place to stay for the night, very well priced, easy to find and was very clean and clutter free. Had easy access to internet and tv without issues. Wendy was very responsive and accommodating.

Luxury 1 Bedroom Apt In The *HEART* Of Orilla
This home was such a gem! We loved Carley’s place as it was right by downtown and walkable to beautiful restaurants in the area. We absolutely enjoyed our stay and will come back and stay at Carley’s for sure!

Suite on the Creek
I have enjoyed my stay very much. Excellent location at the edge of the forest, quiet. I have been also working remotely, internet connection worked perfectly. Kitchen is very well equipped. Thank you Sarah & Jonathan!

Inn on Elm Bala
Thanks Brian and June, had an amazing time . very clean and cozy place, loved the book collection. Super clean appliances and fresh linen. Highly recommend especially if you are a star gazing enthusiast. Dark Sky preserve is near and made the location that much more wonderful.

Sunrise and Bayview with Kayaks & Bikes
This was an amazing adventure for my wife and I it was fantastic. I recommend this place to anyone interested

Lion's Head Bahay
Carina’s place is a small gem - cozy, neat and beautiful with a wonderful backyard. The hosts are very responsive and helpful.

Brookside Studio at Blue Mountain - King Bed
Everything was really good. There were lot of amenities in the place. If anyone is looking for neat and clean place to stay, i would recommend this place. Moreover, there is jacuzzi in there as well.

Ravine 2 Bedroom separate entrance basement apt
This has so far been one of the best rental units I have stayed at. Beautiful location. Lots to do around the area. The rental unit was very spacious, quiet, clean and had everything I needed. The shower is also incredible! Highly recommend staying here!
Condo rentals with outdoor seating

Lovely 3 Bedroom Condo with Stunning View and Pool
We have a wonderful time at Sabine's place, which was an ideal space in every way. It was beautiful, well laid out, and had everything we needed. Sabine was very responsive and accommodating. We would gladly go back when we are next at Blue Mountain.

2BR Getaway at Friday Harbour All Season Resort
Brilliant location for the harbour everything in walkable distance, clean and well stocked kitchen . Responsive host would recommend.

Close to Village, 2 Bedrooms , Rivergrass
We had a great girls weekend away at Bruce’s place! It was very cute and homey, well stocked and very comfortable. Great location too - the shuttle service was a bonus! Unfortunately we had to deal with a wide spread power outage while there but the place was equipped with emergency lights and we made the most out of it. Will definitely be back.

Beautiful Condo, 2 Bedrooms and a Den in a Resort!
Shahed's place at Friday Harbour is beautiful and well appointed. He gave very clear instructions for entry and parking, including photos. The condo was clean and had all the amenities needed, even extra charging cables for devices! The space was comfortable and uncluttered. Shahed was great at communicating and always responded quickly to any questions. Friday Harbour has activities and restaurants available on weekends in the winter and is a fun engaging place by the harbour in the spring, summer and early fall. We were there in the early part of the week in February so the harbourfront was quiet but still nice for a stroll. We spent time in both Barrie (20 minutes away) and Orillia (about 50 minutes away).

2 Bedroom, 2 Level Condo on Blue Mountain!
It was the best location in the village, and it was quiet and the sound of the stream was friendly. If you are skiing during the ski season, it would be very convenient because the bottom of the slope and the entrance to the building are in contact. The interior was clean and well-organized. Thanks, Richard.

Exceptional 2+1 ground floor condo @Friday Harbour
Apartment was even beyond our expectations. It was the most amazing place we have ever rented on New Year holidays. There were 6 people and the place was big and comfortable enough for everybody. Moreover, the apartment was extremely clean and had everything in it to live for short or long terms without any issues. The apartment is located in Friday Harbour which is the perfect place to live in. There are lots of shops, restaurants, a beautiful marina, pool , beach club nearby. We also went for skiing to Horseshoe resort, which took us approx 30 minutes to get there. Shai is a wonderful host, he was in touch during the entire period of our stay in his apartment. He left us a bottle of wine and chocolates as a present, it was so cute. Thank you so much for your attention and care. We will definitely rent your apartment again.

Friday Harbour Luxury Condo, 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

Mountain Side One Bedroom
Connor was great to work with and highly responsive! He sent a very detailed listing of amenities in the area along with locally too like taxis, shuttle services, etc. The place was exactly as advertised. Would stay again!
Quick stats about vacation rentals with outdoor seating in Grey Highlands
Total rentals
550 properties
Nightly prices starting at
ﺩ.ﺇ147 before taxes and fees
Total number of reviews
38K reviews
Family-friendly rentals
450 properties are a good fit for families
Pet-friendly rentals
270 properties allow pets
Rentals with a pool
190 properties have a pool
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- Blue Mountain Village
- Horseshoe Resort
- Mount St. Louis Moonstone
- TPC Toronto at Osprey Valley
- Snow Valley Ski Resort
- Osler Bluff Ski Club
- Beaver Valley Ski Club
- Hockley Valley Resort - Golf, Spa and Ski
- Devil's Glen Country Club
- Cobble Beach Golf Resort Community
- Legacy Ridge Golf Club
- National Pines Golf Club
- Alpine Ski Club
- The Georgian Bay Club
- Toronto Ski Club
- Caledon Country Club
- The Georgian Peaks Club
- Inglis Falls
- The Club At Bond Head
- Shanty Bay Golf Club
- Craigleith Ski Club
- The Pulpit Club
- Mad River Golf Club
- Springwater Golf Course