Cottage vacation rentals in Pickering

Find and book unique cottages on Airbnb

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Popular amenities for Pickering cottage rentals

Pet-friendly cottage rentals

Superhost
A hot tub is positioned on a patio, providing views of the serene lake and distant horizon. Red outdoor chairs surround a firepit, while an umbrella offers shade nearby. The scene is framed by lush greenery and a stony beachfront, enhancing the tranquil setting.
Cottage in Bowmanville
4.89 out of 5 average rating, 159 reviews

“Lakeside Dreams”: All season HotTub w/lake views

CindyRating, 5 stars2 weeks ago
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!
Superhost
A modern living area features a contemporary gray sofa positioned near large windows that offer scenic views of the water. A round glass coffee table sits on a textured rug, and colorful accent pillows enhance the seating area. Natural light fills the space.
Cottage in Bowmanville

Lake Front Escape - Hot tub!

MoonheeRating, 5 stars4 months ago
Spectacular landscape. Hot tube was amazing and the place was spotless! Thank you for memorable experience.
The exterior of a cottage is framed by lush greenery, featuring a wooden facade and a sloped roof. A welcoming porch with a wooden railing overlooks the manicured lawn, adorned with colorful flower beds. Spacious forested grounds surround the building.
Cottage in King City
4.79 out of 5 average rating, 34 reviews

Private Forest Retreat on 9 Acres with Pond

AmyRating, 5 stars37 months ago
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!
A lakeside property is framed by lush greenery and tall trees. The multi-level building features large windows and a welcoming terrace, with a staircase leading down to the water. A wooden dock extends into the lake, providing access to the serene setting.
Cottage in Port Perry

Cheerful 3 Bedroom cottage

MeldonRating, 5 stars34 months ago
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.
Cottage in Blackstock
5 out of 5 average rating, 10 reviews

Country Home in a Forest 4 Bedrooms

AnatRating, 5 stars10 months ago
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!
Superhost
A wooden dock extends over a serene pond, featuring two red Adirondack chairs positioned facing the water. Surrounding trees are visible in the background, reflecting gently on the calm surface of the pond under a clear blue sky.
Cottage in Uxbridge
4.77 out of 5 average rating, 77 reviews

Cozy Hobby Farm Cottage in Uxbridge

MinnaRating, 5 stars4 weeks ago
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!
A spacious deck is shown overlooking a tranquil lake, surrounded by trees. A dog rests comfortably on the wooden surface, while a boardwalk leads down to the water's edge, blending harmoniously with the natural surroundings.
Cottage in Port Perry
4.77 out of 5 average rating, 13 reviews

Pet friendly, Hot Tub and Unli Wi-Fi w/Great View!

AbigailRating, 5 stars4 months ago
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 🧡
Superhost
A serene lakeside scene captures the sun setting over still waters, with clouds reflecting in the calm surface. The shoreline is lined with trees and boulders, creating a peaceful atmosphere conducive to relaxation.
Cottage in Caesarea
4.71 out of 5 average rating, 34 reviews

Cozy Cottage @Lake Scugog *Fire Pit & Game room*

AbigailRating, 5 stars9 months ago
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

Superhost
A spacious living area features large windows offering views of the lake. Comfortable seating is provided by a green sectional sofa and an armchair. A plush ottoman sits in the center, complemented by a soft area rug. Sliding glass doors lead to a deck with outdoor seating.
Cottage in Bowmanville
4.89 out of 5 average rating, 159 reviews

“Lakeside Dreams”: All season HotTub w/lake views

CindyRating, 5 stars2 weeks ago
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!
Guest favorite
A spacious dining area features a long wooden table that accommodates multiple guests. Black chairs are arranged around the table, and large windows allow natural light to illuminate the room, providing views of the surrounding landscape. Neutral tones enhance the inviting atmosphere.
Cottage in Goodwood
4.82 out of 5 average rating, 71 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 Bowmanville

Lake Front Escape - Hot tub!

MoonheeRating, 5 stars4 months ago
Spectacular landscape. Hot tube was amazing and the place was spotless! Thank you for memorable experience.
Superhost
A calm private pond reflects the surrounding trees and sky, with a wooden dock featuring two red chairs positioned at the water's edge. The serene landscape invites moments of relaxation and outdoor enjoyment.
Cottage in Uxbridge
4.77 out of 5 average rating, 77 reviews

Cozy Hobby Farm Cottage in Uxbridge

MinnaRating, 5 stars4 weeks ago
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!
Superhost
An inviting walkway is illuminated by soft lights, leading to a cottage entrance. The deck features a seating area highlighted by string lights. Steps descend from the porch to a landscaped area with a grass border, enhancing the cozy evening atmosphere.
Cottage in Caesarea
4.71 out of 5 average rating, 34 reviews

Cozy Cottage @Lake Scugog *Fire Pit & Game room*

AbigailRating, 5 stars9 months ago
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 !
Superhost
Cottage in Kettleby
4.89 out of 5 average rating, 54 reviews

Gorgeious 5 Bedroom Countryside Cottage in King ON

Melody,ERating, 5 stars3 weeks ago
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
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
Cottage in Hampton
4.85 out of 5 average rating, 108 reviews

Serene 5-BR Bungalow, 3 Full + 2 Half Baths

PradeepRating, 5 stars1 month ago
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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