Cottage vacation rentals in Pickering

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Top-rated cottage rentals in Pickering

Guests agree: these cottages are highly rated for location, cleanliness, and more.

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Top guest favorite

The image shows a lakeside view of the property, featuring a charming brick house with a sloped backyard leading to the water. A boathouse is visible, along with a dock area. Smooth water reflects the soft hues of the sky and surrounding greenery.

Cottage in Wilson

4.98 out of 5 average rating, 209 reviews

Beautiful Lakeside Cottage

LizavetaRating, 5 stars2 months ago

Absolutely amazing stay! We loved the house and it would be great to return. We decided to visit Niagara falls in the winter, it was our first time in the area. I wasn't expecting much of our stay, but it turned out to be a beautiful romantic weekend. The house is right by the lake and has a gorgeous view. You can tell that it was build to be actually used by the hosts and not just a rental property, it is very well-made, cosy, with a lot of nice details and a fully equipped kitchen. We had an great time having breakfast and looking at the lake Ontario. 100% would recommend to stay there!

Superhost

Cottage in Bowmanville

4.83 out of 5 average rating, 154 reviews

Waterfront Beach House Oasis - All Season Hot Tub!

PurvishRating, 5 stars4 days ago

We had an amazing stay at Natalie’s beautiful waterfront property. The view was absolutely stunning and the whole place had such a peaceful, relaxing vibe. The lake-facing backyard with the hot tub was a dream! Perfect for morning coffees and evening soaks. Everything was clean, cozy, and well thought out, and we truly felt right at home. Would definitely come back again!

Guest favorite

A lakeside deck is visible, featuring two loungers and a small side table. The calm water reflects the clouds and surrounding greenery, creating a serene view. The space is bordered by a railing, enhancing safety while enjoying the tranquil scenery.

Cottage in Caesarea

4.89 out of 5 average rating, 35 reviews

Stunning Sunsets on Williams Point

CarolineRating, 5 stars6 months ago

Thank you Sandra so much for letting us enjoy your family cottage for our thanksgiving weekend!! We all loved your place, it’s cozy and the beds are incredibly comfortable. Stunning sunset did not disappoint. We definitely will be back!!!

Guest favorite

A circular fire pit surrounded by four red Adirondack chairs is set on a grassy area by the lake. Small stones form a border around the fire pit, with partial views of the water visible in the background and a wooden dock extending into the lake.

Cottage in Caesarea

5 out of 5 average rating, 15 reviews

Spectacular sunset views at cozy lakefront cottage

YuweiRating, 5 stars3 months ago

We were 8 guys (with possible of more) coming to see a sick friend who is unfortunately nearing the end of life. The place was beautiful and the location was perfect. The weekend was quite cold but the place was welcoming enough that we mostly stayed inside and caught up with old friends. Thank you so much for accommodating our group, you have a very special home!

Guest favorite

The cottage is surrounded by a lush green lawn, with blooming trees adding color to the landscape. A spacious deck extends from the front of the house, inviting outdoor relaxation. The structure features a charming rustic design complemented by a clear blue sky.

Cottage in Aldershot

4.95 out of 5 average rating, 64 reviews

Nature-lovers Cottage Minutes from Downtown

AnnRating, 5 stars5 months ago

We loved our stay at Naiomi’s place. It was private and quaint. Naiomi was so nice to deal with. Her house definitely met our requirements for a place to gather with our family, and she was very receptive to our requests. There is a huge front yard overlooking Lake Ontario where we played games, and a view to die for. She checked in with us several times to make sure we had everything we needed. She ran over with oven mitts when we couldn’t find one; found a bicycle pump for us when we needed it. We would definitely stay here again if we needed to.

Superhost

A serene sunset is captured over the tranquil lake, with soft hues of orange and pink blending into the water. A small boat is visible in the distance, silhouetted against the colorful sky and reflective surface of the lake.

Cottage in Olcott

4.84 out of 5 average rating, 167 reviews

The Castaway Cottage

AshleyRating, 5 stars2 months ago

This was our second time staying, and we will definitely be back. Brian is a wonderful, responsive host. He was very helpful with shoveling when we got stuck in a snow bank due to an unexpected storm. He was kind enough to gift us a bottle of wine, for all the struggles of our weekend. There were some snacks, and bottles of water for us to enjoy.

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What guests are saying

Nature-lovers Cottage Minutes from Downtown

4.95 out of 5 average rating, 64 reviews5 months ago

We loved our stay at Naiomi’s place. It was private and quaint. Naiomi was so nice to deal with. Her house definitely met our requirements for a place to gather with our family, and she was very receptive to our requests. There is a huge front yard overlooking Lake Ontario where we played games, and a view to die for. She checked in with us several times to make sure we had everything we needed. She ran over with oven mitts when we couldn’t find one; found a bicycle pump for us when we needed it. We would definitely stay here again if we needed to.

Cottage in Aldershot

What guests are saying

Beautiful Lakeside Cottage

4.98 out of 5 average rating, 209 reviews2 months ago

Absolutely amazing stay! We loved the house and it would be great to return. We decided to visit Niagara falls in the winter, it was our first time in the area. I wasn't expecting much of our stay, but it turned out to be a beautiful romantic weekend. The house is right by the lake and has a gorgeous view. You can tell that it was build to be actually used by the hosts and not just a rental property, it is very well-made, cosy, with a lot of nice details and a fully equipped kitchen. We had an great time having breakfast and looking at the lake Ontario. 100% would recommend to stay there!

Cottage in Wilson

What guests are saying

Spectacular sunset views at cozy lakefront cottage

5 out of 5 average rating, 15 reviews3 months ago

We were 8 guys (with possible of more) coming to see a sick friend who is unfortunately nearing the end of life. The place was beautiful and the location was perfect. The weekend was quite cold but the place was welcoming enough that we mostly stayed inside and caught up with old friends. Thank you so much for accommodating our group, you have a very special home!

Cottage in Caesarea

What guests are saying

The Castaway Cottage

4.84 out of 5 average rating, 167 reviews2 months ago

This was our second time staying, and we will definitely be back. Brian is a wonderful, responsive host. He was very helpful with shoveling when we got stuck in a snow bank due to an unexpected storm. He was kind enough to gift us a bottle of wine, for all the struggles of our weekend. There were some snacks, and bottles of water for us to enjoy.

Cottage in Olcott