Cottage holiday rentals in Regional Municipality of York

Find and book unique cottages on Airbnb

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Popular amenities for cottage rentals in Regional Municipality of York

Cottage rentals with a hot tub

Cottage in Innisfil
4.83 out of 5 average rating, 105 reviews

Lakeview Oasis 4-bedroom Cottage with Jacuzzi

KimberlyRating, 5 stars4 days 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
Cottage in Innisfil
4.86 out of 5 average rating, 22 reviews

Lakefront Cottage in Innisfil

RafaelRating, 5 stars27 months ago
I recently had the pleasure of staying at Tahnee place. The host was incredibly welcoming and accommodating, making sure that we had everything we needed for our stay. The place itself was beautiful, with breathtaking views and plenty of space for our family. It was clean and had all the amenities we could ask for, from a fully-equipped kitchen to comfortable beds and cozy living spaces.We had a great time as a family, enjoying everything that the property had to offer. I would highly recommend this Airbnb property to anyone looking for a relaxing and enjoyable vacation. The host was top-notch, the place was stunning, and we had a truly memorable time. We would like to come back in the summer to experience it all!
Guest favourite
Cottage in Georgina
4.73 out of 5 average rating, 11 reviews

Farm Retreat – Trails, Chickens & Lake Simcoe

CelineRating, 5 stars2 weeks ago
Sean's place was really spacious and the tasteful finishes on the decor really added to the experience. There was also a welcome note and a gift left for us which was very thoughtful! Instructions were clear, the place was easy to find with ample parking, and Sean was responsive on the app. I highly recommend this place!
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

Cottage in Georgina
4.63 out of 5 average rating, 27 reviews

Cheerful Cottage Near Simco lake

TrevorRating, 5 stars14 months ago
My spouse and I spent four months at Fatemeh's over this past winter. It was a wonderful spot for us to winter while we were constructing our house. Fatemeh and Sepideh were extremely accomodating and hospitable. The house was a quick walk to Lake Simcoe and to groceries and restaurants. Big thanks to Fatemeh for opening her home to us. Top knotch hosts.
Guest favourite
Cottage in Georgina
4.92 out of 5 average rating, 38 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
4.76 out of 5 average rating, 54 reviews

Amazing Cottage Close to Beautiful Lake Simcoe

BlairRating, 5 stars6 days ago
Great little place steps from lake simcoe. had everything we needed and then some. Highly recommend this place
Superhost
Cottage in Brock
4.89 out of 5 average rating, 27 reviews

Unique waterfront Cottage -1.5 hours from T0

DerrickRating, 5 stars9 months ago
We had a great time at Todd's place. Julie and Todd were both easy to reach and helpful whenever we had questions! The location is beautiful and there was a lot to do around the area! would recommend!!
Superhost
Cottage in Uxbridge
4.77 out of 5 average rating, 79 reviews

Cozy Hobby Farm Cottage in Uxbridge

ZachRating, 5 stars4 days ago
Exactly what we were looking for. Jakub was very communicative and the booking, check in and check out process where all very easy. Thanks for a great stay!
Superhost
Cottage in Innisfil
4.85 out of 5 average rating, 34 reviews

Lake Escape Cottage

MitchellRating, 5 stars1 week 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!
Cottage in Innisfil
4.5 out of 5 average rating, 28 reviews

3 Bedroom Cottage Near Friday Harbour and Beaches

AlbertRating, 5 stars3 months ago
Very friendly and helpful host! Love place and a great home layout!

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 Innisfil
4.87 out of 5 average rating, 60 reviews

Beach Kayak Firepit BBQ Luxury Waterfront Cottage

JessicaRating, 5 stars2 weeks ago
We booked this lovely lakefront spot as a place to stay over the weekend of my father-in-law's celebration of life and it suited our needs perfectly as a family of five plus grandma. The main floor bedroom/bathroom suited my mother-in-laws limited mobility needs and we had ample comfortable sleeping/bathroom space for ourselves and our kids upstairs. The house felt fresh, new and very clean with lovely lake views from almost every room. Our only suggestion is that the kayaks could use a little spring cleaning on the inside but it's tough to keep everything outdoors spotless when there is so much rain. Thank you Daman and team!
Guest favourite
Cottage in Georgina
4.8 out of 5 average rating, 20 reviews

Cozy 2 BR Single Family Unit by Lake Simcoe

RosalynRating, 5 stars1 week ago
Cannot thank Soheil enough for coming through for us in having a place to stay. Last minute our booked Airbnb nearby had to cancel on us for our five night stay in the Sutton area~ visiting Family...because of horrible vacationers that nearly destroyed their place. It was SO meant to be to stay at Soheils place instead. The price was great and SO much bigger than our booked little cottage~This was just one of the three floors offered in this beautiful home. Never stayed at an Airbnb that was this peaceful and quiet also. Loved everything ~looking forward to rebooking on our return to the Sutton area.
Top guest favourite
Cottage in Beaverton
5 out of 5 average rating, 22 reviews

Private Waterfront Cottage at Lake Simcoe

AndreaRating, 5 stars2 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, 58 reviews

All-Season Family Homey Cottage near Lake Simcoe!

VanessaRating, 5 stars4 days 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 stars1 month 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 stars3 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

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