Cottage vacation rentals in Pickering

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Top-rated cottage rentals in Pickering

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Top guest favorite

An outdoor seating area features vibrant red and yellow chairs arranged around a coffee table on a wooden deck. A large umbrella provides shade over comfortable seating, with a scenic view of a tranquil pond and lush greenery in the background.

Cottage in Newcastle

5 out of 5 average rating, 36 reviews

Otters Cove Luxury Cottage

Otters Cove is a luxurious Bavarian styled 5bedroom cottage built on pristine 12acre property backing onto hundreds of acres of greenbelt forest trails with a springfed private 1.5acre pond stocked with bass/trout. Over 900 ft of Graham Creek runs through the property which boasts of a seasonal Rainbow Trout/Salmon run. Enjoy Boating, Kayaking, Fishing, Hot tub, Archery, Volleyball, Basketball, wildlife sightings & much more, just an hour's drive from downtown Toronto with yearround road access.

Top guest favorite

A spacious patio overlooks the serene waters of Lake Ontario, featuring a glass railing. A table and several chairs provide seating options, enhancing the area for outdoor dining. The clear blue sky complements the tranquil setting, inviting relaxation.

Cottage in Wilson

4.98 out of 5 average rating, 209 reviews

Beautiful Lakeside Cottage

Located on the shores of Lake Ontario in Wilson, this three bedroom, one bath private home is awaiting your arrival. It is a short distance to wineries, breweries, and restaurants. The backyard oasisis of the lake is ideal for BBQing or just watching the beautiful sunsets. Complete kitchen, gas stove and stainless steel appliances with a dishwasher. All the bedrooms have plush linens. We invite you to enjoy the home we love. Please let us know if you are bringing a dog. There is a $75 pet fee.

Superhost

A spacious outdoor area is set along the pebbled beachfront, featuring a collection of Muskoka chairs arranged for relaxation. Large stones outline the beach, while a fire table and distant trees create a natural backdrop against the blue sky and lake.

Cottage in Bowmanville

4.83 out of 5 average rating, 155 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 living area features a wooden ceiling with skylights and large windows overlooking the woods. A red leather sectional sofa and a wooden coffee table are centered around a small wood stove, with two chairs positioned nearby. Indoor plants are present, adding a touch of greenery.

Cottage in Port Hope

4.71 out of 5 average rating, 52 reviews

Tranquil 3 bedroom cottage among woods & creek

Leave your stress behind as you retreat into this tranquil oasis and stroll the scenic 37 acres of private enchanted forest and flowing creek. Relax and wander the woods taking in the view from windows, chairs, logs . Be inspired as you explore the many lovely nooks and crannies. Just 75 minutes east of Toronto downtown, near to the Ganaraska forest, Brimacombe ski resort, Ganaraska tree top trekking, Rice lake, Cobourg beach, the heritage community of Port Hope with its water front trails

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, 155 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

A serene outdoor space is presented, featuring a grassy area with a circular stone patio. Two wooden adirondack chairs face a small fire pit, with a clear view of the tranquil lake beyond. Lush trees provide natural shade along the shoreline.

Cottage in Burt

4.88 out of 5 average rating, 147 reviews

*HOT TUB | Lake Front | Incredible Views

Welcome to The Sunflower Home! This tranquil home is located right on the lake. Just mins to Olcott Beach, Krull Park & many local wineries. Centrally located yet quietly tucked away, this home is perfect for anyone looking to relax. Enjoy the sunset as you wind down in the hot tub, sip your beverage of choice, fireside, overlooking the lake, or head inside and enjoy the view from every window. Go to sleep on the comfortable king bed & wake up to the serenity of Lake Ontario.

Guest favorite

A peaceful waterfront scene features a wooden dock extending over the shimmering lake. Adirondack chairs sit invitingly at the end of the dock, framed by gentle waves and soft sunlight. A charming windmill decoration is positioned among the greenery, enhancing the natural setting.

Cottage in Scugog

4.95 out of 5 average rating, 19 reviews

Lakeside｜Cozy Waterfront Cottage

Welcome to our charming waterfront cottage, a hidden gem nestled along the serene shores. Immerse yourself in the tranquility of nature as you wake up to the gentle lapping of waves and picturesque views. Whether you seek a romantic retreat or a peaceful escape, our cottage offers a cozy haven where modern comforts meet the timeless allure of waterfront living. Discover the perfect blend of relaxation and adventure in this idyllic retreat – your home away from home awaits.

Guest favorite

A lakeside deck is visible, featuring two loungers and a small side table. The calm water reflects the clouds and surrounding greenery, creating a serene view. The space is bordered by a railing, enhancing safety while enjoying the tranquil scenery.

Cottage in Caesarea

4.89 out of 5 average rating, 35 reviews

Stunning Sunsets on Williams Point

Enjoy beautiful sunsets every night in this seasonal cozy, charming 3-season, rustic cottage rental, located just 1 hour east of Toronto, on Lake Scugog in Ceasarea. Spectacular view of the lake and sunsets. Only 1 hour from Toronto, 20 minutes to Port Perry and the Blue Heron Casino. This cozy, 4-bedroom cottage hosts a unique 50's style diner kitchen, spacious lakeside deck with gazebo and large dining table. Perfect to dine and watch the stunning sunsets.

Guest favorite

Two vibrant red Adirondack chairs are positioned on a wooden deck overlooking the lake. A decorative potted plant adds greenery to the scene. Calm waters stretch out to the horizon, with a few boats visible in the distance under a clear blue sky.

Cottage in Caesarea

5 out of 5 average rating, 16 reviews

Spectacular sunset views at cozy lakefront cottage

Escape to an exclusive retreat with stunning lakefront views, blending tranquility with adventure. Perfect for family vacations, romantic getaways, or creative retreats. This cottage offers kayaking, paddle boarding, swimming, evening fires and breathtaking sunsets. Explore historic downtown Port Perry and add some excitement at the Great Blue Heron Casino. Discover the perfect blend of serenity and adventure at this exclusive retreat. Your ideal getaway awaits!

Superhost

A grassy backyard area is framed by wooden fencing and shaded by mature trees. Multiple black Adirondack chairs surround a stone fire pit, providing a comfortable space for gatherings. Lake Wilcox is visible in the background, reflecting the blue sky and clouds.

Cottage in Richmond Hill

4.93 out of 5 average rating, 152 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

Superhost

A serene view of a beach cottage is presented across the water. Brightly colored outdoor chairs are arranged on the lawn, set against the backdrop of a well-maintained garden and trees. The cottage features a flat roof and wide windows that invite natural light.

Cottage in Little Britain

4.84 out of 5 average rating, 31 reviews

Little B. Lake house (cottage)

Kick back and relax in this calm, stylish cottage on the beach. Fully renovated, spacious home, surrounded by trees, a unique location right on to Lake Scugog . Stress-free, peaceful and exclusive vacation spot. located at very quite area, a 20-minute drive from beautiful Lindsy downtown where you can find unique boutique and all amenities. 1 hour 20 minute from Toronto. A place to enjoy, Jacuzzi, fire pit, barbecue or your quite scape into nature.

Guest favorite

An aerial view of the property reveals a spacious yard bordered by greenery and farmland. The cottage is seen from above, showcasing a deck with seating and a mini-golf area nearby. Ample parking can be noted at the side of the house.

Cottage in Burlington

4.85 out of 5 average rating, 97 reviews

The Pearl Lodge

Almost 1 acre of land for you and your family to enjoy Free parking on premises Beautiful 4 bedroom cottage Comfortably sleeps 10 people Enjoy mini golf, pool table, and table tennis Open concept lounge and sitting area BBQ and firepit available for your use Walkout to deck with beautiful view of massive backyard Covered patio Soccer/Volley ball available upon request Located within minutes to trails, Lake Ontario, shopping and much more.