House vacation rentals in Grey Highlands

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Popular amenities for Grey Highlands house rentals

House rentals with a pool

Superhost
Home in The Blue Mountains
4.89 out of 5 average rating, 218 reviews

Large 4 Br - 4.5 Bath; Sauna/Shuttle Bus/2 King bd

AliceRating, 5 stars2 days ago
It is a wonderful house, furnished in every detail, it offers many entertainments to have fun with your family. My children had a great time. The house is in a quiet and relaxing location surrounded by nature.
Superhost
Home in The Blue Mountains
4.87 out of 5 average rating, 104 reviews

Spacious 4BR Snowbridge Home with Shuttle Access

AleksandarRating, 5 stars1 month ago
Very nice and spacious home with plenty of room for a large group to spread out. Loved the open concept kitchen and dining area and felt plenty close to Blue Mountain village and skiing.
Guest favourite
Home in The Blue Mountains
4.95 out of 5 average rating, 192 reviews

Serene mountainside home View/Shuttle Bus/Pool

LisaRating, 5 stars2 weeks ago
We had a wonderful stay - Brendan's place was clean, organized and in a great area (close to village). Brendan was responsive and helpful and I would recommend this place to relax and enjoy Collingwood.
Top guest favourite
Home in Desboro
4.97 out of 5 average rating, 122 reviews

Forest Loft - Forest, Sauna, Ponds & Stargazing

StaceyRating, 5 stars2 weeks ago
My brother, father and I really enjoyed staying at the loft! Valentine provided us with everything we could have asked for and more. We will definitely be recommending this space to our friends and family :)
Superhost
Home in East Gwillimbury
5 out of 5 average rating, 3 reviews

10 Acre Farmhouse with Pool + 5 Bedrooms/3 Baths

PaulRating, 5 stars3 months ago
This place was absolutley spotless and communication was amazing even though nothing was needed til checkout. Would love to have enjoyed pool but tough in January. Minimal amount of snow fell and they had someone come shovel and salt.
Superhost
Home in Owen Sound
4.87 out of 5 average rating, 69 reviews

Custom Mansion on the Water | Pool | Hot Tub

AndrewRating, 5 stars16 months ago
This is the second time we’ve booked a stay here - from the outside it doesn’t seem nearly as big as it actually is inside. A beautiful home with a ton of space for 14-16 of us, with enough amenities that you don’t have to leave at all during your stay, but there are also multiple nearby trails and parks to explore. The dishwasher was broken during our stay, which was quite an inconvenience for a large group, but Nicholas was accommodating and fairly responsive. Due to the holiday season there was no one available to repair it but we were fairly compensated for our troubles.
Guest favourite
Home in Kimberley
4.88 out of 5 average rating, 197 reviews

Heart of Kimberley - with views and a hot tub

TeresaRating, 5 stars1 month ago
Thanks for a great stay!
Superhost
Home in Chatsworth
4.89 out of 5 average rating, 145 reviews

Stonehaven - large country retreat, with pool*

TawnyaRating, 5 stars1 month ago
We struggled to find a place for our group of 17 and Stonehaven was an amazing find! The beds were comfortable, we loved being able to have meals all together in one spot, and there was lots of space for people to do different activities inside since it was winter. Outside, we enjoyed tobogganing, snowshoeing and cross country skiing on the property. Steve was quick to communicate and provided clear instructions and maps. We were already talking about going back so we can enjoy the property in the summer! Thank you for a memorable and fun weekend!

Weekly house rentals

Guest favourite
Home in Wasaga Beach
4.88 out of 5 average rating, 8 reviews

WoWSaga peaceful 3bdr close to Blue Mountain

RobRating, 5 stars9 months ago
Nice place about a 10 min walk to the beach down some quiet side streets. Great fire pit in the back but the pull out couch leaves something to be desired if you sit on the wrong spot. Loved the vinyl collection and the path across the street.
Superhost
Home in Barrie
4.75 out of 5 average rating, 8 reviews

King Beds with Home Gym and Large Backyard Oasis

MichaelRating, 5 stars3 weeks ago
We had a great stay in Barrie! The place was clean, cozy, and exactly as described. The host was super responsive and made everything easy. Would definitely stay again!
Top guest favourite
Home in Innisfil
4.98 out of 5 average rating, 217 reviews

Luxe Villa with Sauna and Hot Tub @ Lake Simcoe

IrinaRating, 5 stars1 month ago
We loved the place—cozy and perfect for a relaxing weekend getaway. I really appreciated the early check-in and later check-out. Thank you! I would definitely recommend this stay
Top guest favourite
Home in Wasaga Beach
4.79 out of 5 average rating, 52 reviews

Great Family Get Away - Wasaga Beach (2) wifi

AmberRating, 5 stars7 months ago
Rocco was an incredible host, accommodating to every extent possible. The place was spotless, equipped with everything you could ever need, and just steps away from the beach. To top it off, there's an amazing ice cream shop just two steps away—what more could you ask for? Rocco truly made us feel right at home and ensured our stay was comfortable and enjoyable from start to finish. I can't recommend this place enough! I just hope this review doesn’t come back to bite me, as it might mean less availability in the future for us! Def looking forward to our next visit!
Guest favourite
Home in Orangeville
4.86 out of 5 average rating, 42 reviews

Stunning 5 Bedroom Family Home

JeffRating, 5 stars2 months ago
House was perfect for our group of 8. Will stay again next time we’re in the area
Guest favourite
Home in Wasaga Beach
4.91 out of 5 average rating, 11 reviews

Townhouse 5 min to Wasaga Beach

VidalRating, 5 stars2 months ago
This is a beautiful home. It is very clean and perfect for anyone. We definitely recommend staying here and would come back again. The owners were extremely responsive to any of our questions.
Guest favourite
Home in Tiny
4.88 out of 5 average rating, 50 reviews

Sandy beach getaway

MaryRating, 5 stars8 months ago
We had an amazing stay at the cottage. Everything was spotless and welcoming. Kitchen had everything we needed and we enjoyed our meals on the large deck. Located in a quiet and peaceful area. Short walk to a beautiful, clear, sandy beach. We enjoyed many spectacular sunsets. Great beach for kids. We enjoyed our stay and would highly recommend.
Guest favourite
Home in Collingwood
4.9 out of 5 average rating, 192 reviews

JJ’s Collingwood bar & games house.

PrabhkaranRating, 5 stars4 days ago
Jer was a very good host, the place was beautiful, bunch of games to play, had a lot of fun. The surroundings are beautiful 10 min walk to park and beach. 10 minutes drive to blue mountain. The place was really good.

Private house rentals

Superhost
Home in Waubaushene
4.79 out of 5 average rating, 38 reviews

All season/Ski/Waterfront/Fish Modern Cottage

DilaraRating, 5 stars6 months ago
We had a wonderful stay in this AirBnB! The view is a dream. You are reliant on a car here, as you can't get very far on foot, but the nearest supermarket is just a 5-minute drive away.
Superhost
Home in Shelburne
4.65 out of 5 average rating, 26 reviews

The Old Millinery House

SmRating, 5 stars3 months ago
We had a wonderful stay at the Old Mill in Shelburne. The property is charming and full of character, offering both comfort and tranquility. Lynn is a generous and thoughtful host, making our visit truly special. Highly recommended!
Guest favourite
Home in Port McNicoll
5 out of 5 average rating, 7 reviews

Swan Cove Waterfront Retreat

Nicole De SousaRating, 5 stars8 months ago
Evgenia's home was overall ABSOLUTELY STUNNING! From the beautiful water front views to the gorgeous amenities, my entire group was in awe of what was right in front of us. We had such an amazing stay, made even better memories and felt right at home during our stay. It was truly a great "home away from home" experience! We were so lucky to get the chance to feed the swans during our stay, we were shocked at the amount of wildlife that appeared thereafter. During our stay we were able to bring a boat & jet ski. We docked the jet ski at the property's dock and were able to launch the boat/jet ski at the Victoria Harbour in the area. Unfortunately we were unable to bring the boat to the home's dock due to low tide this year, but hopefully when we book again we can dock both at the house :) We would 100% recommend Evgenia's place for anyone looking for a quiet luxurious getaway with the most spectacular views!
Guest favourite
Home in The Blue Mountains
5 out of 5 average rating, 22 reviews

Large 4 br and 3 full bathroom/Sauna by Village

NícolasRating, 5 stars1 month ago
Our stay was awesome, the house is amazing, very close to the slopes and the amenities were great!
Guest favourite
Home in Singhampton
4.86 out of 5 average rating, 35 reviews

5+ bdr Cottage Collingwood Blue Mountain Singhamp

JamieRating, 5 stars3 months ago
Nancy’s Airbnb was an absolutely fantastic experience! From the moment we booked, Nancy’s communication was flawless—prompt, clear, and incredibly friendly. She provided detailed instructions and helpful tips that made our stay seamless. The property itself was immaculate, cozy, and exactly as described, with thoughtful touches that made it feel like home. Nancy clearly takes pride in hosting, as every detail was carefully considered, from the well thought out social spaces to the well-stocked amenities. Her hospitality truly stood out—she was always available to answer questions and went above and beyond to ensure we had everything we needed. It’s rare to find a host so dedicated to creating a memorable experience. We couldn’t recommend Nancy’s Airbnb more highly and will absolutely stay here again!
Superhost
Home in Barrie
4.88 out of 5 average rating, 97 reviews

Entire House, Private/Clean 5bdr 6 Beds/Sleeps 12

Umrat KhamisRating, 5 stars2 weeks ago
Hi Sina! Thanks for hosting me and my family. The house was beautiful and clean. We enjoyed every minute of it. The area was very serene and had a sense of home in it. It was also near many wonderful tourist sites as well convenient stores. Although, it was a bit cold, so we couldn't enjoy it to the fullest. But we very much hope to revisit in the summer.
Superhost
Home in Owen Sound
4.93 out of 5 average rating, 117 reviews

Century Home in downtown Owen Sound - Hot Tub

KevinRating, 5 stars4 months ago
Excellent place to stay. Very clean. Very accommodating.
Superhost
Home in Stayner
4.8 out of 5 average rating, 5 reviews

BlueFornia Ski Snow Sweet Home Winter

KerineRating, 5 stars7 months ago
beautiful and clean place. 100% privacy as it was surrounded by trees. . everything you needed was there. .would highly recommend

Quick stats about house rentals in Grey Highlands

  • Total rentals

    270 properties

  • Total number of reviews

    7.3K reviews

  • Family-friendly rentals

    240 properties are a good fit for families

  • Pet-friendly rentals

    110 properties allow pets

  • Rentals with a pool

    60 properties have a pool

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

Destinations to explore

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