Cottage vacation rentals in Pickering

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Top-rated cottage rentals in Pickering

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Superhost

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!

Discover the perfect pet-friendly haven just 45 mins from Downtown Toronto with hot tub, unlimited Wi-Fi, stunning sunset & sunrise views! Lakeridge Hideaway is 1km from 2 ski resorts and steps to the private dock on Chalk Lake. Sleeps 6 adults + 4 children, featuring open-concept living, fully renovated kitchen & rooftop outdoor shower. Explore mountain bike trails & enjoy the canoe & kayaks. Cozy up with the woodstove, 55” smart TV with Netflix & Disney+ and DVD library. Escape the city today!

Guest favorite

An aerial view showcases a stone cottage-style house with a green roof, surrounded by lush greenery and trees. A winding driveway leads to the property, where two vehicles are parked, set against an expansive green lawn.

Cottage in Goodwood

4.84 out of 5 average rating, 79 reviews

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

We offer discounts for 3 nights and more :) Our house is built like an old English-style stone house cottage and is approximately 1 hour from downtown Toronto. The house is great for special occasions and getting away from it all with a group of friends or family. We've included some fun extras such as a projection theater room, slate snooker table, cable TV, BBQ and an outdoor hot tub for those nights you want to relax. We supply seasoned firewood for the indoor wood fireplace, so have fun :)

Superhost

Aerial view of a spacious bungalow set in a large green landscape. The property is surrounded by trees and open fields, with a long driveway leading to the entrance. Nearby structures and a natural setting contribute to a serene atmosphere.

Cottage in Hampton

4.87 out of 5 average rating, 119 reviews

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

Stay at our tranquil Bowmanville bungalow! Free parking, Wi-Fi, fire pit, BBQ included. 5 bedrooms for 16 guests. 4000 sqft, 3 full baths, 2 half baths, kitchen, living room. Ideal for family/friends. Near Cedar Park Resort Note Beds for 16 guests 5 extra folding beds available on request at no extra cost Maximum capacity: 21 guests Please inform us in advance if bringing additional visitors or hosting an event. No underage/teen parties allowed. Violation may result in booking cancellation

Guest favorite

A charming cottage is nestled within a lush green landscape, surrounded by a variety of shrubs and flowering plants. The red-brick façade and dark roof are complemented by a tall chimney, while the inviting entrance is framed by greenery.

Cottage in High Park North

5 out of 5 average rating, 14 reviews

The Cottage in High Park - Free Parking!

Escape to our city oasis! Nestled in High Park/Bloor West Village, our charming cottage offers urban tranquility just 15 mins from downtown by subway. Ride a bike to the beach, wander the tree-lined streets, explore boutiques in the local village, or forest-bathe deep in the trails of High Park. Return to cozy comfort, a wood-burning fireplace, a game of charades, or step out to a covered patio, perfect for BBQ creations or a movie under the stars. Your urban-cottage escape begins here!

Tall cedar trees create a serene setting, with sunlight filtering through the branches. The ground is covered in fallen leaves, and a glimpse of a modern country home is visible in the background among the vibrant greenery and autumn foliage.

Cottage in Blackstock

4.83 out of 5 average rating, 12 reviews

Country Home in a Forest 3 Bedrooms

Your Countryside Dream! This modern executive country home offers serenity and bliss. Surrounded by tall cedar trees, it is an ideal get-away from the busy city life. Perfect for families & couples looking for adventure and to explore the country. Close to local farms, wineries, ski resorts, conservation areas, and Canadian Tire Motorsport Park. Situated on the Oakridge's Moraine, near hidden valleys, hiking trails, hills and nearby small creeks & rivers. Easily accessible from the 407 & 401.

Guest favorite

A serene view of Lake Ontario at dusk is captured, with calm waters reflecting soft pink and blue hues. Wooden steps lead down to the water, accompanied by paddles and life-saving equipment positioned on a deck.

Cottage in Bowmanville

5 out of 5 average rating, 11 reviews

East Beach Waterfront Cottage

Welcome to your lakeside escape on beautiful Lake Ontario; a cozy, stylish cottage retreat perfect for families, couples, or small groups. With stunning water views, private decks that lead right to your swimming area, and a hot tub overlooking the lake, this is the ultimate spot to unwind and recharge. Whether you’re here to relax, explore Bowmanville/Port Darlington, or enjoy evenings under the stars, this cottage is a perfect all-season getaway. Book your stay and wake up to the waves.

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

4.75 out of 5 average rating, 4 reviews

Lake Front Escape - Hot tub!

Escape to our tranquil waterfront retreat just minutes from the city! This stunning 4-bedroom, 3-bathroom home offers breathtaking lake views, vibrant sunsets, and endless amenities, including kayaks, a fire pit, BBQ, and an all-season hot tub. Relax indoors with a movie, lounge on the private pebble beach, or explore the nearby Darlington conservation areas. Whether you’re seeking relaxation, adventure, or both, our serene getaway is the perfect place to unwind and create lasting memories.

Guest favorite

An aerial view reveals a spacious countryside cottage surrounded by lush greenery, showcasing a well-maintained lawn and mature trees. The property features a large driveway leading to a two-car garage, with a pathway guiding towards the entrance of the home.

Cottage in Kettleby

4.9 out of 5 average rating, 60 reviews

Gorgeious 5 Bedroom Countryside Cottage in King ON

Gorgeous 5-Bedroom Countryside Cottage - located in a quiet family neighborhood at a beautiful 3-acre lot with a huge lawn and woodlot, Lots of Parking, a minute's drive to The Manor Event Center, Hwy 400 & 427, groceries, restaurants, Golf Club, beautiful trails, Green Belts, farmers markets, Apple and strawberry picking. 20 min. to Lake Simcoe boating and fishing, many nearby shopping malls, TTC Subway, Go Station, and Canada's Wonderland. Please Note: Strictly no drug and booze parties.

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

4.9 out of 5 average rating, 172 reviews

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

Escape to our stunning lakefront family cottage! Enjoy breathtaking views, modern comforts, and the serenity of cottage life. With a private beach, firepit, BBQ, and covered patio, relaxation is guaranteed. Explore the nearby conservation area's trails or cast your line at the fishing creek, just a short walk away. A public beach is 5 min walk. Indulge in the perfect blend of nature and convenience. Book your stay now and create unforgettable memories in our charming cottage retreat!

An aerial view captures a spacious manor surrounded by lush greenery, with a driveway leading to the entrance. A circular pond is positioned in the foreground, while an RV is parked beside the building, providing a glimpse of available outdoor space.

Cottage in Uxbridge

5 out of 5 average rating, 3 reviews

Priv Magical Forest Manor 30+Disco KTV Party Room

Privacy Manor, 15 Acres Forest Surrounded, over 30+ disco party room & KTV system, waterfall, fountain, outdoor kitchen, short-term stays, retreats and small events. 4000ft interlocking can set a outdoor event. Close golf course and ski resorts, at Uxbridge Perfect for families looking to make the most of the season or for companies wanting to host a corporate retreat. Our Magical Forest Manor is able to host up to guests inside the Cottage. Extremely private with an elevated view.

Guest favorite

A garden path lined with stepping stones leads to a view of the Toronto skyline across the water. Green grass and plants surround a patio table and chairs, providing a serene setting with trees framing the picturesque scene.

Cottage in Toronto

4.94 out of 5 average rating, 71 reviews

Toronto Island Cottage

This beautifully furnished, bright, and airy cottage is located just eight minutes south of the city, on the picturesque Toronto Island. This is a unique opportunity to experience all that the islands offer in a stylish setting. Perfect for a staycation or vacation, the cottage is well-equipped with everything you need to make the most of your time. The serene community is accessible only by ferry or water taxi. The view of the Toronto Harbour and skyline is absolutely epic – enjoy!

Superhost

A wooden dock extends into a serene lake, reflecting a clear blue sky with scattered clouds. Flower pots are positioned on the dock, while torches line the edges, contributing to a peaceful outdoor atmosphere.

Cottage in Richmond Hill

4.94 out of 5 average rating, 161 reviews

White Oak on Wilcox-Richmond Hill Lakefront Oasis

Welcome to The White Oak on Wilcox - a lakefront oasis in the heart of Richmond Hill, perfect for an all-season getaway. Located just 30 mins from Toronto, enjoy direct access to Lake Wilcox with beautiful sunset views from the private dock. This vacation home welcomes you to a relaxing and serene lakefront experience. Surrounded by numerous activities to enjoy year-round, this is the perfect home-away-from-home! Share your memories with us @whiteoakcottageco