Cottage vacation rentals in Pickering

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Popular amenities for Pickering cottage rentals

Cottage rentals with a hot tub

A wooden dock extends into the calm waters, leading towards a two-story cottage surrounded by lush greenery. The cottage features large windows reflecting the evening light. A fire pit and seating arrangement are visible on the grassy area, enhancing the outdoor experience.
Cottage in Caesarea
4.63 out of 5 average rating, 41 reviews

Gorgeous Waterfront Cottage 1 Hour from Toronto

PalakRating, 5 stars4 months ago
I recently stayed at this lovely Airbnb, and it was exactly what I needed for a relaxing weekend getaway. The host was incredibly welcoming and provided clear instructions for check-in, which made everything so easy. The place itself was spotless, well-maintained, and exactly as described in the listing.
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.
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.
A heated hot tub is situated under a wooden gazebo, surrounded by bare trees and a snowy landscape. Steam rises gently from the water, creating an inviting atmosphere for relaxation in the serene outdoor setting.
Cottage in Brampton
4.83 out of 5 average rating, 6 reviews

100% Private & Spotless ~ 5BR Cottage ~ Hot Tub

SimeonRating, 5 stars3 days ago
Thanks for a beautiful and lovely stay. Everything was amazing.
A spacious living room features large windows offering a view of the lake at sunset. Leather seating surrounds a central coffee table, with soft lighting enhancing the inviting space. A foldable sofa bed is positioned near the windows, creating a cozy area for relaxation.
Cottage in Caesarea
4.75 out of 5 average rating, 4 reviews

Gorgeous Waterfront Cottage 1 Hour from Toronto

KateRating, 5 stars10 months ago
We had an amazing stay. The lake was perfect and cottage had everything we needed. We enjoyed the volleyball nets, hottub, board games and dock. The water was shallow and calm and perfect for swimming. A local boat place delivered and picked up Standup paddle boards which was perfect. We wert not too far from port Perry where we enjoyed lunch and walk around the local shops. Overall this was a great trip for a few moms a group of our teen daughters. Adults had rooms and washroom upstairs and kids enjoyed the rooms and bathroom downstairs. Great trip!!
The cottage exterior is nestled among lush greenery, showcasing a contemporary design with dark walls and vibrant red accents. A pathway leads to the entrance, framed by a variety of plants and trees, enhancing 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 stars5 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 🧡
A serene lakeside property is nestled among lush greenery, featuring a multi-level structure with a sloped path leading down to the water. Tall trees surround the building, creating a peaceful atmosphere, while the clear blue sky above enhances the tranquil setting.
Cottage in Port Perry

Cheerful 3 Bedroom cottage with hot tub

Pet-friendly cottage rentals

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!
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!
A charming blue house is surrounded by a lush green lawn, with colorful flower beds and ferns defining the outdoor space. Two blue chairs are positioned on the patio, and large windows invite natural light into the inviting entryway.
Cottage in Caesarea
5 out of 5 average rating, 4 reviews

Entire Cottage on Lake Scugog

JackieRating, 5 stars10 months ago
This is our second time staying here so please read my review from last year as it has more detail. This place provides a perfect old fashioned cottage experience and reminds me of childhood holidays. We love how easy it is to get here and how peaceful it is when we arrive. The lake is lovely to swim in and the west facing views gave us amazing sunsets. As noted in my first review, the cottage is exactly as described in the listing.
Cottage in Caesarea

2BR Cottage Escape: Lake Scugog w/ Sauna & Hammock

Private cottage rentals

A verdant forest area is depicted, featuring an array of green foliage and white flowers in the foreground. A tall tree stands prominently, surrounded by lush greenery and dappled sunlight filtering through the leaves.
Cottage in Pickering
4.53 out of 5 average rating, 58 reviews

Private Cottage Getaway in Nature

DianaRating, 5 stars2 weeks ago
What a wonderful space! Top-notch girls weekend getaway with a ton of space, a beautiful grassy yard with an outdoor pool. Peaceful and private location. Also, the cottage is enormous with a ton of bedrooms and everything you need for a comfy stay. Rachel is a flexible, friendly and responsive host. I'd recommend this property and Rachel to anyone! A space to host a big group is a rare find. Thanks, Rachel!
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.
Guest favorite
Cottage in Toronto
5 out of 5 average rating, 9 reviews

The Cottage in High Park - Free Parking!

DianaRating, 5 stars3 weeks ago
The house is delightful and it was a pleasure staying there for two weeks in spring. It is stylish and comfortable. We especially loved the outdoor sitting area just outside the French doors in the living room. Kim’s music collection and great stereo sound system were a plus. The kitchen had everything one could think of and we cooked meals. The principal bedroom is pretty, roomy and quiet. The neighbourhood is leafy and quiet and we liked the fact it is an easy walk to the Bloor subway, Bloor West Village shops and to High Park. Kim was very friendly, responsive and a great host. It felt like a perfect home and we were sorry to leave.
An open kitchen area features light wood cabinetry and a mix of modern appliances. A large dining table crafted from dark wood is surrounded by several chairs. Natural light enters through the sliding glass door, illuminating the stone-patterned backsplash and countertop.
Cottage in Richmond Hill
4.69 out of 5 average rating, 13 reviews

Cottage Bungalow Retreat

KomalRating, 5 stars17 months ago
Tharsini is a wonderful host. This cottage is adorable and very private. My expectations were perfectly met, and it was an amazing place to hold a get together. Thank you so much Tharsini for your communication and being a lovely host!
A serene outdoor space is framed by vibrant red and orange trees, with fallen leaves carpeting the ground. Several benches are positioned in a circular formation, providing a view of the distant lake under a partly cloudy sky.
Cottage in Pickering Beach
4.63 out of 5 average rating, 165 reviews

Beautiful Lakeview Cottage on the Beach!!

TanishkaRating, 5 stars5 days ago
The location was amazing and the cottage was very well kept and spacious. It had a vintage aesthetic and had everything we needed for our little celebration! Jaeson was a great host and everything was above my expectations:)
Guest favorite
A picturesque walkway is lined with lush greenery and flowering plants. The path, made of cobblestones, leads past manicured shrubs and trees, providing a serene entrance to the cottage. Muted colors from autumn leaves can be seen in the background, enhancing the natural setting.
Cottage in South Parkdale
4.95 out of 5 average rating, 22 reviews

Unique Cottage Hidden in Toronto's Artsy West End

CarmelaRating, 5 stars9 months ago
Kelly is a great host and it was a pleasure to meet her during our stay. She arranged for an earlier check in and a late check out due to our stay being for medical reason. She is very proactive and a great communicator and her attention to details didn’t go unnoticed. There was a beautiful bouquet of flowers and a welcoming card waiting for us upon our arrival. Our home away from home was as pictured. It was nicely furnished, great decor and very clean. The bed was very comfortable and the bathroom/shower very modern. The TV included several streaming apps which was definitely a plus. The location is in a quiet residential area and within walking distance to coffee shops, restaurants and grocery stores. Would definitely recommend this place and we hope to come back again.
Cottage in Scugog
4.84 out of 5 average rating, 61 reviews

Lakefront cottage close to Toronto

CraigRating, 5 stars11 months ago
Very charming and rustic cottage with a beautiful backdrop. We stared at the lake for endless hours through the window in the sun room, and enjoyed sunsets sitting on the dock. If you have young kids, this place is a dream come true. Between the adorable kids room filled with toys, puzzles and books, the pirate ship play structure in the yard, and the countless water activities, your little ones will have no shortage of things to do. There's also lots to do in the area. We enjoyed eating and shopping in downtown Port Perry, strawberry picking at a local farm, and the numerous parks and beaches in close proximity. I would definitely recommend and we look forward to returning!

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