Cottage vacation rentals in Pickering

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Top-rated cottage rentals in Pickering

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The image shows a lakeside view of the property, featuring a charming brick house with a sloped backyard leading to the water. A boathouse is visible, along with a dock area. Smooth water reflects the soft hues of the sky and surrounding greenery.

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 living area showcases large windows offering views of the lake. Neutral-colored furnishings are arranged for comfort. A large Smart TV is mounted on the wall, and a decorative plant adds a touch of greenery to the space.

Cottage in Bowmanville

4.83 out of 5 average rating, 156 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 calm private pond reflects the surrounding trees and sky, with a wooden dock featuring two red chairs positioned at the water's edge. The serene landscape invites moments of relaxation and outdoor enjoyment.

Cottage in Uxbridge

4.78 out of 5 average rating, 74 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.

Guest favorite

A spacious green yard is framed by a canopy of trees, enhancing the serene outdoor space. Two red structures are visible in the background, harmonizing with the natural landscape. A soft blue sky with wispy clouds adds to the peaceful setting.

Cottage in Burt

4.8 out of 5 average rating, 71 reviews

LaVida Cottage - a restful creekside destination

LaVida Cottage offers a quaint and quiet setting two blocks from Lake Ontario and overlooking 18 Mile Creek. In the 3/4 acre back yard there is a FIREPIT, two patios, picnic spots and plenty of places to pitch a family tent. The yard overlooks a very active wetland with all sorts of wildlife. Please note our rental rate includes the 5% local bed tax. There is excellent guest security (although Olcott is very safe) with exterior cottage lighting and video monitoring of the parking area.

Superhost

A spacious living area features large windows offering views of the lake. Comfortable seating is provided by a green sectional sofa and an armchair. A plush ottoman sits in the center, complemented by a soft area rug. Sliding glass doors lead to a deck with outdoor seating.

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

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.

Superhost

A serene lakeside fire pit area features two red Adirondack chairs positioned around a stone circle. Lush green grass surrounds the space, and a wooden fence offers a view of the calm water, complemented by trees and a clear blue sky above.

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 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 tranquil deck area features comfortable seating with decorative cushions. A small table holds various plants, while the lush green surrounding trees provide privacy. The view beyond includes glimpses of the water, enhancing the serene outdoor environment.

Cottage in Little Britain

4.8 out of 5 average rating, 30 reviews

Cozy Lakeview Cottage | Kawartha Lakes Getaway

Peaceful Atmosphere: Relax in serene surroundings with nature's soothing sounds. Water Access: Short stroll to the water's edge for swims, relaxation, kayaking, and ice fishing. Open Design: Cathedral ceiling, large windows, patio doors for deck access. Family Fun: Bunk beds, teepees, board games for kids' enjoyment. Scenic Views: Panoramic lake and field views from the spacious deck. Enjoy boho decor, coffee bar, firepit, WiFi.

Guest favorite

A vibrant row of cottage-style buildings in pastel colors is depicted, with a person in a pink dress walking along a wooden pathway. Decorative flowers hang from the blue and pink cottages, while a lighthouse stands in the background against a clear sky.

Cottage in Burt

4.81 out of 5 average rating, 341 reviews

Anchors Away Cottage with Hot tub!

Experience Niagara Falls USA and Lake Ontario like a local! You'll enjoy a restful sleep in our Anchors Away cottage right within walking distance of a public pebble beach. Our quaint cottage is just minutes from Olcott Beach, the Niagara Wine Trail, and world-famous fishing along Eighteenmile Creek and Burt Dam. Niagara Falls is about 30 miles away and the Buffalo metropolitan area is about 40 miles away.