Cottage vacation rentals in Pickering

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Top-rated cottage rentals in Pickering

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The cottage exterior is enveloped by lush greenery, showcasing a modern design with large windows and a spacious balcony. Stone steps lead to a well-maintained garden, and natural stone pathways are visible, enhancing the serene outdoor setting.

Cottage in Port Perry

4.83 out of 5 average rating, 12 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

The exterior of a charming stone cottage is displayed, featuring a sloping roof and large windows that allow for ample natural light. A spacious wooden deck is shown adjacent to the house, surrounded by grassy areas and trees, indicating a peaceful outdoor setting.

Cottage in Goodwood

4.81 out of 5 average rating, 70 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 :)

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

4.85 out of 5 average rating, 107 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

Cottage in Toronto

5 out of 5 average rating, 8 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!

Cottage in Blackstock

5 out of 5 average rating, 10 reviews

Country Home in a Forest 4 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.

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Cottage in Bowmanville

4.83 out of 5 average rating, 153 reviews

Waterfront Beach House Oasis - All Season Hot Tub!

Welcome to our serene waterfront sanctuary! This stunning 4-bed, 3-bath retreat is the perfect escape just outside the city. Enjoy unobstructed lake views, sunsets, kayaks, fire pit, BBQ, and a year-round hot tub. Relax indoors with a movie or on the private pebble beach. Explore nearby Darlington conservation areas for hiking and wildlife. Our home offers everything you need for the ultimate urban getaway. Whether you seek relaxation, adventure, or natural beauty, your perfect retreat awaits!

Superhost

A spacious entryway features light-colored walls and modern lighting. A wooden bench is positioned near the doorway, alongside a decorative console. The front door, adorned with a circular glass insert, opens to a welcoming foyer, with a hallway leading further into the home.

Cottage in Kettleby

4.88 out of 5 average rating, 51 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.

A tranquil deck overlooks the calm pond, surrounded by trees. Two lounge chairs with red cushions and a small table are positioned invitingly, perfect for relaxing while enjoying the natural scenery.

Cottage in King City

4.79 out of 5 average rating, 34 reviews

Private Forest Retreat on 9 Acres with Pond

A Quiet Picturesque Forest Retreat. Ideal for romantic trips, quiet family getaways, alone time, connecting with nature, relaxing and recharging! If you want to get away from it all, this is the place! Deck on pond, firepit, stargazing, bird watching. COVID-19 safe - 3 days blocked between stays - No parties please! - 2 beds, 1.5 baths Bathroom with shower Equipped kitchen/living room 3 season room for rainy days Wood burning stove/fireplace King bed in master Queen bed in 2nd bedroom

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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

4.79 out of 5 average rating, 73 reviews

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.

Superhost

Aerial view of a charming cottage situated along a pebbled shore, with clear waters lapping at the sandy beach. Nearby, trees stand tall, and the landscape is dotted with outdoor seating for relaxation. The serene lake reflects the sky, creating a tranquil atmosphere.

Cottage in Bowmanville

4.89 out of 5 average rating, 154 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!

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

4.73 out of 5 average rating, 33 reviews

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

Bala’s cottage is a tastefully decorated cottage on a quaint hamlet 15 minutes from Port Perry. It is your home away from home. So much to do: BBQ as you enjoy the breathtaking sunset over the lake, relax on the gazebo swing, roast marshmallows in the firepit table in the deck, hit the game room to play Pool, Air-hockey or Table tennis, board games, WFH from the home office with desk & chair. Close to marina where you can rent kayaks, boats, catamarans and launch your own boat to fish.

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!