Cottage holiday rentals in Regional Municipality of York

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Popular amenities for Regional Municipality of York cottage rentals

Cottage rentals with a hot tub

Cottage in Innisfil
4.83 out of 5 average rating, 107 reviews

Lakeview Oasis 4-bedroom Cottage with Jacuzzi

KimberlyRating, 5 stars1 week ago
Our group of seven really enjoyed our stay here. Hosts were super communicative and helpful when we had questions, and even allowed us to check in a couple of hours early upon request. The home itself was clean, in a great location on the water, and had everything we needed for our stay - including the kitchen, which was stocked with all of the cooking tools and utensils we needed for the weekend. Area is super peaceful, and with tons of amenities on the property, we practically lived outside for the weekend. Would recommend a stay here, especially for a larger group. Thank you Weiqi and Shuyan for a great stay!
Guest favourite
Cottage in Goodwood
4.82 out of 5 average rating, 72 reviews

Family fun! Hot tub/snooker table/Movie Room!

BenjaminRating, 5 stars1 month ago
I stayed at this air b&b with 14 people. We thoroughly enjoyed our time and the host was great & very responsive! Highly recommend if you are looking for some time away or need a home base for a large group just outside of Toronto
Superhost
Cottage in Georgina
4.93 out of 5 average rating, 15 reviews

Cozy Lakeside Cottage With Private Hot Tub

MarcRating, 5 stars4 months ago
Amir was great! And the place was awesome. Very responsive and helpful with everything we needed. We will be back for sure!
Guest favourite
Cottage in Georgina
4.75 out of 5 average rating, 12 reviews

Farm Retreat – Trails, Chickens & Lake Simcoe

NiRating, 5 stars1 day ago
Thank you, Sean for opening up your place for us to spend the weekend! My friends and I thoroughly enjoyed our stay. We could tell the property was well taken care of, everything was clean, all the decorations were adorable, and the house/backyard were super spacious. We would recommend this airbnb!
Cottage in Georgina
4.82 out of 5 average rating, 17 reviews

Lakeview cottage with hot tub and sauna

LauraRating, 5 stars13 months ago
Beautiful private cottage, we would love to come back again!
Cottage in Innisfil
4.83 out of 5 average rating, 110 reviews

Hot Tub / BANYA / Sauna - True Cottage experience

HannahRating, 5 stars1 month ago
Arthur's place was great, close to the park and beach which was awesome. The amenities in the backyard were great and easy to use. There is a property caretaker that lives in basement suite, which I didn't notice in the listing until after we had booked, he was very friendly just unexpected. We had a great stay, activities for the whole family!
Cottage in Georgina
4.72 out of 5 average rating, 29 reviews

Modern waterfront Cottage with Hot Tub & Fire Pit

ChristyRating, 5 stars9 months ago
Lisa’s place was perfect for a quick getaway for my husband and I! We loved the house, found it well equipped to just stop for some groceries and then spent all of our time relaxing. We couldn’t believe how crystal clear the lake was and how quiet and peaceful it was! The bed was comfortable, and we enjoyed the hot tub and fire pit!
Cottage in Innisfil
4.64 out of 5 average rating, 39 reviews

Unique Beach House Perfect for Romantic Getaway

RobRating, 5 stars9 months ago
Great place, great area, great host.

Pet-friendly cottage rentals

Guest favourite
Cottage in Georgina
4.92 out of 5 average rating, 39 reviews

Cozy 4 Bdr Cottage Near Lake Simcoe & Beaches

GrahamRating, 5 stars1 month ago
Accommodation was exactly as shown and described with added squirrels and chipmunks dashing around outside! Fab place in a fab location, close to a fab freshwater lake and fab bar at the end of the road.
Cottage in Innisfil
4.52 out of 5 average rating, 48 reviews

Cozy Cottage 5Min Walk/1Min Drive to Private Beach

NavdeepRating, 5 stars1 month ago
Had a wonderful time at this cozy cottage. It was clean, peaceful, and surrounded by nature. Everything we needed was provided. Would definitely stay again!
Cottage in Innisfil
4.6 out of 5 average rating, 57 reviews

Charming 1 bedroom cottage - steps from the beach

MarcusRating, 5 stars2 months ago
The place was very nice and cozy. In a good area. Nice back yard. Did have an air hockey and fuzzball table as well. There was quite a bit of dog/animal fur on the beds and extra bed sheets but besides that, very nice and clean place. Would recommend
Cottage in Innisfil
4.76 out of 5 average rating, 54 reviews

Amazing Cottage Close to Beautiful Lake Simcoe

BlairRating, 5 stars1 week ago
Great little place steps from lake simcoe. had everything we needed and then some. Highly recommend this place
Cottage in Georgina
4.62 out of 5 average rating, 37 reviews

Cottage at Lake Simcoe

DeannaRating, 5 stars2 weeks ago
Our group enjoyed our stay at Min's cottage. It was as described in the listing, comfortable and with everything we needed for our stay. Min was quick to respond to our questions and was flexible regarding our check-in. We would stay here again.
Superhost
Cottage in Brock
4.89 out of 5 average rating, 28 reviews

Unique waterfront Cottage -1.5 hours from T0

ClaireRating, 5 stars1 day ago
We had a such a lovely stay at Todd’s place. The location is wonderful comfy beds powerful showers, plenty of towels and lots of mod cons. A sandy swimmable beach is outside your front door and from the back deck watch the boats go by dawn till dusk. Bliss. Very responsive host and lovely getaway.
Superhost
Cottage in Innisfil
4.85 out of 5 average rating, 34 reviews

Lake Escape Cottage

MitchellRating, 5 stars2 weeks ago
Absolutely beautiful place, I would 100% comeback and I would highly recommend this spot to anyone. The host was very nice and responsive. I had a great time!
Superhost
Cottage in Innisfil
4.64 out of 5 average rating, 22 reviews

Cozy 2 bdrm cabin steps from beach

LeeRating, 5 stars8 months ago
Second time staying at Rachel's- lovely cottage and a great location. Rachel was extremely helpful and easy to communicate with. Thanks again!

Private cottage rentals

Guest favourite
Cottage in Georgina
4.91 out of 5 average rating, 33 reviews

Cheerful 2-bdrm cottage 2 minute walk to the lake

MeaghanRating, 5 stars9 months ago
Place was clean and very well accommodated
Superhost
Cottage in Georgina
4.76 out of 5 average rating, 83 reviews

Spacious Lakeside Cottage for Families & Groups

AadhithyaRating, 5 stars1 month ago
Had a great time and memories at Soheil' s place. he was very responsive and a great host!! one of the ceiling fan in the main bedroom wasn't working and he was quick to help us with alternate. it felt like home, check in and check out process was hassle free. little disappointed that the Jacuzzi wasn't working. overall, it was worth and a perfect weekend get away for our group. gave the proper small town vibe!!!
Top Guest favourite
Cottage in Beaverton
5 out of 5 average rating, 23 reviews

Private Waterfront Cottage at Lake Simcoe

AndreaRating, 5 stars3 weeks ago
What a great place! We had 11 people. 6 adults and 5 children. There were beds for everyone and because the weather was crap (totally not Byron’s fault - LOL) we were inside most of the weekend. There was enough space and internet bandwidth to keep everyone happy and engaged! Everything was comfortable and the kitchen had everything we needed! Hope to rent this next year for family fun weekend!
Guest favourite
Cottage in Innisfil
4.93 out of 5 average rating, 59 reviews

All-Season Family Homey Cottage near Lake Simcoe!

VanessaRating, 5 stars1 week ago
With our two other bookings falling through days/hours before our planned trip, Mr&Mrs Nathan helped us out with booking their beautiful home 2hrs before check in. Also, with the last minute booking of their home, it was very clean and ready for us when we arrived with such a short notice. It fit our party of 9 comfortably, backyard was a great asset to relax as well. Felt like a home away from home. Would definitely go back in the future.
Superhost
Cottage in Innisfil
4.79 out of 5 average rating, 14 reviews

Cozy 2 Bedroom Cottage with beach 5 min walk away!

JeannineRating, 5 stars2 months ago
Very responsive host as this was a last minute booking and she was super accommodating. Great place and convenient location.
Guest favourite
Cottage in Innisfil
4.8 out of 5 average rating, 44 reviews

Spacious Lake Simcoe Retreat

SimonRating, 5 stars4 weeks ago
This renovated 3-bedroom cottage was a fantastic find—quiet, private, a few minutes’ drive from the public beach/local parks. While you’ll need a car to access amenities, the location is peaceful. The exterior could use post-winter TLC—a cleanup of spring debris and a good wash. The inside of the cottage is spacious, stylish, and thoughtfully laid out. The photos don’t capture how roomy and comfortable it is. The beds were comfortable; fresh and dining areas were well-appointed. We were five adults and had more than enough space to spread out and enjoy. One minor drawback was the unreliable internet—it needed frequent resets and wasn’t great for streaming or remote work. Our host, Mandy, was excellent: friendly, quick to respond, and incredibly helpful throughout our stay. If you plan to cook, bring all ingredients. The KEURIG coffee maker was fun to use and there were a few K cup pods for us when we arrived. We had a fabulous time and would return in a heartbeat.
Superhost
Cottage in New Tecumseth
4.84 out of 5 average rating, 55 reviews

THE WHITE HOUSE ON THE HILL Beautiful Country Home

GordonRating, 5 stars5 months ago
Our stay was fantastic. The White House on the Hill lived up to its billing. The view was spectacular and yes at the top of the hill. Liliana was a great host. Very responsive when we needed her. We had our families their for Christmas and the Holiday, Liliana decorated the house for us. A Christmas tree, decorations and many wonderful things that made us feel like it was our own house for Christmas. We enjoyed the modern kitchen and counter space. The dinning area was spacious and perfect for serving. The family/ Great Room was very cozy. A comfortable leather L couch for us to curl up and enjoy movies. The wood burning stove added so much to the room. The warmth, ambience and smell of the fire was like an old cottage. All wood was provided. Liliana was very gracious letting us have a later check out on January 1. We stayed from December 26th to January 1 and had a fantastic experience. We would recommend the White House on the Hill 5 STARS. We will be there again Rose, Gord & Family
Superhost
Cottage in Innisfil
4.86 out of 5 average rating, 70 reviews

Rustic Waterfront Cottage - Perfect for WFH

PooyaRating, 5 stars9 months ago
We had a wonderful experience with this Ahh’s Cottage! They were incredibly kind, responsive, and always positive throughout our stay. The place was spacious, extremely clean and very comfortable, easily accommodating our group of 10. The instructions provided were clear and made our stay hassle-free. Highly recommend staying here!

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