Cottage vacation rentals in Pickering

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Top-rated cottage rentals in Pickering

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Guest favourite
Two individuals are seen rowing in a small red boat on a clear, tranquil pond, surrounded by lush greenery and trees. The sun casts gentle reflections on the water, enhancing the serene atmosphere of the natural setting.
Cottage in Newcastle
4.97 out of 5 average rating, 58 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 natural 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.

Guest favourite
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
4.87 out of 5 average rating, 142 reviews

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

Top guest favourite
Cottage in High Park North
5 out of 5 average rating, 19 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!

Guest favourite
An aerial view showcases a stone cottage-style house with a green roof, surrounded by lush greenery and trees. A winding driveway leads to the property, where two vehicles are parked, set against an expansive green lawn.
Cottage in Goodwood
4.81 out of 5 average rating, 84 reviews

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.

Guest favourite
Cottage in Bowmanville
4.97 out of 5 average rating, 29 reviews

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.

Guest favourite
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
4.81 out of 5 average rating, 110 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
A hot tub is positioned on a patio, providing views of the serene lake and distant horizon. Red outdoor chairs surround a firepit, while an umbrella offers shade nearby. The scene is framed by lush greenery and a stony beachfront, enhancing the tranquil setting.
Cottage in Bowmanville
4.88 out of 5 average rating, 188 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!

Guest favourite
A welcoming entrance is framed by light-colored siding and features a blue door. An American flag is displayed, while a stone pathway leads to a landscaped area with green plants and decorative stones. A white bench adds to the functional outdoor space.
Cottage in Olcott
4.8 out of 5 average rating, 154 reviews

Althea Corner

Here is your getaway filled with entertainment and relaxation! This is the center of it all! Steps away from shops (seasonal), bars, restaurants and park, you'll have fun while you recharge. There's room for your boat and docks are one minute away! Inside you will enjoy an open floor plan with three private bedrooms, applianced kitchen, dining area and full bath. Plenty of ammenities for outside fun as well! We can't wait to host your stay! Please note: $25 per night per guest over 2

Guest favourite
A modern kitchen features sleek white cabinetry with gold hardware and a spacious countertop. Stainless steel appliances, including a refrigerator and oven, are neatly arranged. Natural light filters in through a window, illuminating the glossy tile flooring and minimalistic decor.
Cottage in Richmond Hill
4.94 out of 5 average rating, 170 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

Top guest favourite
A serene sunset view is captured over the lake, with the sun casting a golden glow on the water. The image features the edge of a spa tub in the foreground, with gentle ripples of water visible. A blue chair is positioned nearby, inviting relaxation.
Cottage in Barker
4.95 out of 5 average rating, 100 reviews

Lake Front Vista & HotTub

Enjoy Spectacular Lakefront views. Relax at your own pace. Take a dip in the spa tub or just enjoy the scenery Very quiet road Speedy internet Fire-pit Enjoy the Niagara Wine Trail 2 Bdrm 6 min to Golden Hill Park 12 min to White Birch Golf course 15 min to Olcott/Burt (fishing charters) 20 min to Waterport/Kent (fishing charters) 50 min to Niagara Falls *Promo: 3rd night or more, will be discounted ~25% (no discount on cleaning and fees, excl 06/23-09/10)

Top guest favourite
A private deck is showcased, featuring two black chairs facing a serene lake view. Lush green trees and foliage surround the area, enhancing the peaceful atmosphere. The calm water reflects the blue sky, creating an inviting spot for relaxation.
Cottage in Caesarea
4.99 out of 5 average rating, 97 reviews

Lakeside Cottage Getaway South Shore Lake Scugog

WELCOME TO YOUR LAKESIDE GETWAY! This ALL SEASONS rustic, private lakefront cottage (south shore of Lake Scugog) has 2 bedrooms, 2 queen sized beds, large bright living/dining room, pullout couch, newly renovated kitchen and bathroom, private dock, indoor fireplace/outdoor fire pit and a loft space. Located approximately 1.5 hours from Toronto, this cottage is the perfect place for families and friends to escape the hustle and bustle, relax and unwind.

Guest favourite
The image captures a serene sunset over the water, with vibrant orange and yellow hues reflecting on the surface. A dock extends into the water, accompanied by gentle silhouettes of trees along the bank. The scene conveys a sense of tranquility at day's end.
Cottage in East Gwillimbury
5 out of 5 average rating, 8 reviews

Watrfrt Cottage | Sunset Views & 45 Min to Toronto

Bright 3-bed, 3-bath custom waterfront cottage home just 40 mins north of Toronto! Sleeps 8 with a king, 2 queens & a futon. Modern kitchen, open living space, and private backyard with dock, fire pit and pergola lounge. Canoe included for water adventures. Enjoy sunsets, relaxing by the water, by the bon fire, and creating memorable moments in a peaceful, private setting while being just 10 minutes away from downtown Newmarket.

Popular amenities for Pickering cottage rentals

Quick stats about cottage rentals in Pickering

  • Nightly prices starting at

    Pickering vacation rentals start at $261 CAD per night before taxes and fees

  • Verified guest reviews

    Over 260 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Pickering rentals

  • 4.7 Average rating

    Pickering stays receive an average rating of 4.7 out of 5 from guests

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