Cottage holiday rentals in Oshawa

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Top-rated cottage rentals in Oshawa

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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, 125 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

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

4.84 out of 5 average rating, 81 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.

Tall cedar trees create a serene setting, with sunlight filtering through the branches. The ground is covered in fallen leaves, and a glimpse of a modern country home is visible in the background among the vibrant greenery and autumn foliage.

Cottage in Blackstock

4.83 out of 5 average rating, 12 reviews

Country Home in a Forest 3 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.

Top guest favourite

A serene view of Lake Ontario at dusk is captured, with calm waters reflecting soft pink and blue hues. Wooden steps lead down to the water, accompanied by paddles and life-saving equipment positioned on a deck.

Cottage in Bowmanville

5 out of 5 average rating, 15 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.

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

4.89 out of 5 average rating, 177 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!

A modern living area features a contemporary gray sofa positioned near large windows that offer scenic views of the water. A round glass coffee table sits on a textured rug, and colorful accent pillows enhance the seating area. Natural light fills the space.

Cottage in Bowmanville

4.8 out of 5 average rating, 5 reviews

Waterfront Oasis – All-Season Hot Tub!

Escape to our serene waterfront retreat just minutes from the city! This stunning 4-bedroom, 3-bathroom home offers breathtaking lake views, vibrant sunsets, and amazing amenities including kayaks, a fire pit, BBQ, and an all-season hot tub. Spend cozy evenings indoors with a movie, unwind on the private pebble beach, or explore the nearby Darlington conservation areas. Whether you’re seeking peace, adventure, or both, our lakeside haven is the perfect escape for unforgettable memories.

An aerial view captures a spacious manor surrounded by lush greenery, with a driveway leading to the entrance. A circular pond is positioned in the foreground, while an RV is parked beside the building, providing a glimpse of available outdoor space.

Cottage in Uxbridge

5 out of 5 average rating, 6 reviews

Priv Magical Forest Manor 30+Disco KTV Party Room

Privacy Manor, 15 Acres Forest Surrounded, over 30+ disco party room & KTV system, waterfall, fountain, outdoor kitchen, short-term stays, retreats and small events. 4000ft interlocking can set a outdoor event. Close golf course and ski resorts, at Uxbridge Perfect for families looking to make the most of the season or for companies wanting to host a corporate retreat. Our Magical Forest Manor is able to host up to guests inside the Cottage. Extremely private with an elevated view.

A spacious living area features a combination of light and vibrant orange walls, enhancing the room's brightness. Comfortable seating options include a sectional sofa and armchairs, with a central table surrounded by decorative plants. Soft lighting highlights a cozy atmosphere, complemented by decorative artwork.

Cottage in Pickering Beach

4.64 out of 5 average rating, 191 reviews

Beautiful Lakeview Cottage on the Beach!!

Beautiful Retro-style Cottage in south Ajax Ontario right on the famous Paradise Beach! Only 20 minutes east of Toronto - be in the Nature and Relax with the whole family at this peaceful waterfront cottage. This unique place has a style of its own with over 2000 sq ft of living area.

A private cottage is showcased from the perspective of a sparkling outdoor pool. The structure features a two-story design with a wooden balcony and large windows surrounded by lush greenery and colorful landscaped gardens.

Cottage in Pickering

4.56 out of 5 average rating, 66 reviews

Private Cottage Getaway in Nature

Make some memories at this unique and family-friendly cottage. This spacious, private home resides on a hill, ambient with the beautiful views of the surrounding nature. Enjoy your stay!