Cottage vacation rentals in Pickering

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

Stay at our tranquil Bowmanville bungalow! Free parking, Wi-Fi, fire pit, BBQ. 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 Truck parked in front 5 extra folding beds available on request at no extra cost Maximum capacity: 20 guests Inform us in advance if bringing additional visitors or hosting an event. No underage/teen parties allowed. Violation may result in booking cancellation

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

Late check in Dec 30 or early Dec 31 available! Discounts for 3 or more nights. 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. We supply seasoned firewood for the indoor wood fireplace, so have fun.

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.

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.

5-BR Home Near Toronto - Large Backyard & Fire Pit

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.

“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!

Country House On 100 Acres Of Land

Have you ever wanted the experience of living on a 100 acre well manicured farm? We are located on a very scenic and quite private street with a paved road. We are surrounded by other beautiful private farms. We are a hay farm so no animal noise just 100 acres beautiful fields and forest. Each property is boarded with tens of thousands of trees separating one farm from another. Close to Blue Heron casino, Lake Scugog. Just 55 min from downtown Toronto, 10 mins from the free 407 off ramp.

Waterfront Oasis – All-Season Hot Tub!

Escape to our serene waterfront retreat just minutes from the city! This stunning 4-bedroom, 3-bathroom home offers breathtaking lake views, vibrant sunsets, and amazing amenities including kayaks, a fire pit, BBQ, and an all-season hot tub. Spend cozy evenings indoors with a movie, unwind on the private pebble beach, or explore the nearby Darlington conservation areas. Whether you’re seeking peace, adventure, or both, our lakeside haven is the perfect escape for unforgettable memories.

Signature King City Cottage Escape

Escape to this charming 3+2 bedroom cottage-style home nestled on a large, tree-filled lot in beautiful King City. Surrounded by nature, the home offers the peaceful feeling of a private retreat—while still being just minutes from everyday essentials. Wake up to birdsong, enjoy your morning coffee among mature trees, and unwind in the quiet serenity. Whether you’re planning a weekend escape or a family stay, this home delivers the best of both worlds: nature, comfort, and convenience.*

Cottage in Toronto’s West End •Walk to BMO Field•

A hidden cottage retreat in Toronto’s vibrant west end—just 15 minutes walk to BMO Field with no traffic or crowds. Tucked away on a quiet, tree-lined laneway, this fully renovated 1800s cottage offers a rare mix of charm, privacy, and location. Enjoy the energy of the city—Queen West, Ossington, Liberty Village —then come home to your own peaceful escape. Perfect for World Cup visitors, families, and remote workers. Stay close to everything, without sacrificing calm and comfort.

Away to Relax! Lake View, 2nd floor, Private Bath

Enjoy cottage life while you visit Toronto. An opportunity to relax, unwind and step away from the hustle and bustle. access downtown via public transit or by car. Your second floor suite has a king bed, Private bath, private deck & panoramic view of Lake Ontario. Clean, Safe Space, Free (street) parking, Fast WIFI, Beautiful neighborhood, easy walk to public transit. Award winning garden, Good feng shui, Heaven for birders, Designated Superhost more than 25 times!

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