
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.
Vacation rentals for every style
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Popular amenities for Pickering cottage rentals
Cottage rentals with a hot tub

Lake Front Escape - Hot tub!
Spectacular landscape. Hot tube was amazing and the place was spotless! Thank you for memorable experience.

Cheerful 3 Bedroom cottage
Irina’s cottage is lovely! Very spacious and comfortable, elegantly furnished, and cool even in hot weather,. The rooms have large picture windows with spectacular views of Chalk Lake. Irina was a very gracious and helpful host. The lake itself is very quiet and serene, perfect for swimming and kayaking.

Pet friendly, Hot Tub and Unli Wi-Fi w/Great View!
We had a great time for our girls weekend! Very beautiful landscape and property, the house is fully stocked with everything you could need for your stay and more. Comfortable sleeping areas and living spaces. Christine from cottage link was super quick to help us when we needed assistance. Thanks so much for hosting us, we will for sure be booking again 🧡

Cheerful 3 Bedroom cottage with hot tub
Pet-friendly cottage rentals

“Lakeside Dreams”: All season HotTub w/lake views
Sachin was incredibly responsive and fulfilled our requests instantly. The cottage was amazing—exactly as described on Airbnb. We had a wonderful stay and truly appreciated the hospitality! It truly felt like home, and we’re already looking forward to coming back next year!

Lake Front Escape - Hot tub!
Spectacular landscape. Hot tube was amazing and the place was spotless! Thank you for memorable experience.

Private Forest Retreat on 9 Acres with Pond
Natalie’s cabin is the perfect escape from the city. The best part about it is you aren’t driving hours to get there it’s convenient but also just so relaxing and gorgeous! The nature there was exquisite and the land itself is surreal. The place is so clean, spacious, quiet! Natalie has a gorgeous little pond with a dock just perfect to enjoy some wine or your morning coffee. The firepit was so much fun at night with some s’mores. The bbq was well kept! The land is just picturesque. My (then) boyfriend proposed to me on Natalie’s dock and it was just truly magical. I would recommend this property to anyone I could! 5/5 will go back again!

Cheerful 3 Bedroom cottage
Irina’s cottage is lovely! Very spacious and comfortable, elegantly furnished, and cool even in hot weather,. The rooms have large picture windows with spectacular views of Chalk Lake. Irina was a very gracious and helpful host. The lake itself is very quiet and serene, perfect for swimming and kayaking.

Country Home in a Forest 4 Bedrooms
We had a wonderful time at Sarah's beautiful, clean and well equipped house. Sarah was very responsive and helpful, and filled the kitchen with everything we needed, including seasoning, cooking and baking items and more. Also, let's not forget the fresh farm eggs and the herbs garden. Beds are super comfortable as well as all other furniture. We enjoyed the peaceful and beautiful garden and the gazebo, also highly recommended for star gazing at night! Thanks Sarah!

Cozy Hobby Farm Cottage in Uxbridge
Thank you to Jakub for a lovely stay at the Cozy Hobby Farm. The cottage was a perfect spot for our family to gather for the weekend. The kids were thrilled with the large trampoline, and the adults had fun playing pool and ping pong. Everyone enjoyed an evening campfire together. The cottage was beautiful and had plenty of space for our large group to feel comfortable. Jakub was quick to respond to my questions. A wonderful spot to enjoy with family!

Pet friendly, Hot Tub and Unli Wi-Fi w/Great View!
We had a great time for our girls weekend! Very beautiful landscape and property, the house is fully stocked with everything you could need for your stay and more. Comfortable sleeping areas and living spaces. Christine from cottage link was super quick to help us when we needed assistance. Thanks so much for hosting us, we will for sure be booking again 🧡

Cozy Cottage @Lake Scugog *Fire Pit & Game room*
Our stay at Bala’s place was a fantastic experience. We were a group of 8 including 4 tween aged children. The cottage is very well located , close to Port Perry and around 45 min to Peterborough. Lots of places to visit within the Trent Severn Waterway area. Bala graciously allow us an early check-in. His place is very cute, neat, super clean and had everything we needed to prepare meals and to entertain both children and adults alike. The game room is a great addition to the cottage. Walking distance to Lake Scugog, we were able to have nice walks after a delicious BBQ dinner. The deck and the fire pit allowed us to share quality family time while enjoying nature at its best. Thank you Bala for such a warm welcome with popcorn and soda !!. We appreciated very much your always friendly and promptly response to our needs. I will definitely recommend anyone to have a great and relaxing experience at your cottage. It is worth it !
Private cottage rentals

“Lakeside Dreams”: All season HotTub w/lake views
Sachin was incredibly responsive and fulfilled our requests instantly. The cottage was amazing—exactly as described on Airbnb. We had a wonderful stay and truly appreciated the hospitality! It truly felt like home, and we’re already looking forward to coming back next year!

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

Lake Front Escape - Hot tub!
Spectacular landscape. Hot tube was amazing and the place was spotless! Thank you for memorable experience.

Cozy Hobby Farm Cottage in Uxbridge
Thank you to Jakub for a lovely stay at the Cozy Hobby Farm. The cottage was a perfect spot for our family to gather for the weekend. The kids were thrilled with the large trampoline, and the adults had fun playing pool and ping pong. Everyone enjoyed an evening campfire together. The cottage was beautiful and had plenty of space for our large group to feel comfortable. Jakub was quick to respond to my questions. A wonderful spot to enjoy with family!

Cozy Cottage @Lake Scugog *Fire Pit & Game room*
Our stay at Bala’s place was a fantastic experience. We were a group of 8 including 4 tween aged children. The cottage is very well located , close to Port Perry and around 45 min to Peterborough. Lots of places to visit within the Trent Severn Waterway area. Bala graciously allow us an early check-in. His place is very cute, neat, super clean and had everything we needed to prepare meals and to entertain both children and adults alike. The game room is a great addition to the cottage. Walking distance to Lake Scugog, we were able to have nice walks after a delicious BBQ dinner. The deck and the fire pit allowed us to share quality family time while enjoying nature at its best. Thank you Bala for such a warm welcome with popcorn and soda !!. We appreciated very much your always friendly and promptly response to our needs. I will definitely recommend anyone to have a great and relaxing experience at your cottage. It is worth it !

Gorgeious 5 Bedroom Countryside Cottage in King ON
Kaleem's property is everything promised. I would recommmend to my friends and will rebook when needed. Kaleem is a great host who over delivers

THE WHITE HOUSE ON THE HILL Beautiful Country Home
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

Serene 5-BR Bungalow, 3 Full + 2 Half Baths
Loved the stay! We were group of 20 and the entire group had so much fun. Lots of activities and games. Plenty of space to accommodate 20 ppl. Sripathy was responsive and easy to reach.
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- Rogers Centre
- Scotiabank Arena
- CN Tower
- University of Toronto
- Budweiser Stage
- Distillery District
- Port Credit
- Metro Toronto Convention Centre
- Toronto Zoo
- TPC Toronto at Osprey Valley
- Exhibition Place
- The Danforth Music Hall
- CF Toronto Eaton Centre
- Harbourfront Centre
- Massey Hall
- BMO Field
- Trinity Bellwoods Park
- Jackson-Triggs Niagara Estate
- Royal Woodbine Golf Club
- Casa Loma
- Dufferin Grove Park
- Royal Ontario Museum
- Cobourg Beach
- Hockey Hall of Fame