Cottage holiday rentals in Pickering

Lakefront Cottage + Boathouse & Sunsets

Lakefront summers with spectacular sunsets, private dock, and a relaxed boathouse hangout. Spend your days kayaking, paddleboarding, swimming, and fishing, then wind down with evening fires and sunset views over the lake. The cottage is a cozy, comfortable space for easy family lake days, with room to gather, unplug, and enjoy time together. When you feel like exploring, historic downtown Port Perry is just minutes away, along with local wineries, breweries, live music, and day-trip adventures.

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

3BR on Lake Simcoe | Gorgeous Views 1hr From City

Escape the city and unwind at our peaceful three-bedroom lakefront cottage on Lake Simcoe, just one hour north of Toronto. With 129 feet of private waterfront, expansive lake views, and shallow swimmable shoreline, it’s the perfect year-round getaway for families, couples, or friends looking to relax and reconnect. 🌅 Stunning sunrise lake views 🏖️ 129 ft of private waterfront 🏊 Shallow, swimmable shoreline 🔥 Cozy all-season retreat 🌲 Quiet and peaceful setting 🚗 Just 1 hour from Toronto

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.

Scugog Lake House - with hot tub and Sauna

Enjoy a getaway in the city of Kawartha Lakes while just a stone throw from all the city has to offer at our vacation home at Lake Scugog. Enjoy this luxuriously furnished house and spend your time soaking up the sun from our waterfront property and cooling off by catching a few waves. Blow off some steam in the sauna, also have a party in the hot tub. The lake house is newly renovated with luxury amenities throughout. Enjoy canoeing, kayaking, and fishing at Lake Scugog directly off the dock.

5-Acre Waterfront Cottage w/sauna，Pool & Hot Tub

Welcome to "the Easy Time", an escape to unforgettable luxury at our waterfront cottage on Lake Scugog, less than 1 hour drive from Toronto. The property includes 5 acres of wooded land, 280ft of waterfront, 2700sq. ft. four season main cottage, an A-framed Bunkie, and a domed tent. The cottage is open and spacious, providing a generous living area with stunning views of the water all around with multi-level decks, outdoor sauna, swimming pool, hot tub, shower, firepit, and extra long dock.

Cozy Hobby Farm Cottage in Uxbridge

*4 SEASONS COTTAGE*Stunning cottage retreat at Uxbridge,where you can enjoy the perfect balance of tranquility and entertainment.Our 4-bedroom cottage sleeps up to 12 guests, it's the ideal location for families or groups of friends looking to unwind and make lasting memories. You can also take advantage of our BBQ space,you can grill up mouthwatering burgers and steaks while taking in the fresh country air.The barn is not part of the rental and there are no animals inside or in property.

“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!

Cottage in Toronto’s West End • Near Downtown

A hidden cottage retreat in Toronto’s vibrant west end. Tucked away on a quiet, tree-lined laneway, this fully renovated 1800s cottage offers a rare blend of charm, privacy, and location. Explore Queen West, Ossington, Liberty Village, Exhibition Place, the waterfront, and downtown—then return to your own peaceful retreat. Perfect for families, couples, business travellers, and remote workers, it’s an ideal place to experience the city without sacrificing comfort and tranquility.

Waterfront Cottage - Fire Pit, Dock, 1Hr Toronto

Four-season retreat on Lake Scugog! 🍁 Breathtaking fall colours and lakefront views. 🔥 Fireplace and cozy living room with blankets & games. 💻 Wi-Fi great for digital nomads. 🍴 Fully equipped kitchen for family meals. 🐾 Pet-friendly – bring your furry friend. Couples’ getaways, families, remote workers, weekend escapes. Enjoy crisp mornings with coffee on the deck. Cozy nights by the fireplace. [A/C units and Dock access will be closed after Thanksgiving in October.]

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

Lakeview Oasis 4-bedroom Cottage with Jacuzzi

Our lakeside home in Cook's Bay — 4 bedrooms, 2 bathrooms, sleeps up to 9 — is just an hour from the GTA. Wake up to sunrise over the lake, use our private dock for kayaking and paddleboarding, or unwind by the fire pit and hot tub. You may spot geese and ducks by the lake — they won't block access. Pet-friendly: please clean up after your dogs and keep them off neighbouring properties. Note: per city regulations, the dock is removed mid-October to mid-May.