Cottage vacation rentals in Oakwood

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Top-rated cottage rentals in Oakwood

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Top guest favorite
A spacious outdoor seating area features comfortable wicker chairs and a grill, surrounded by soft lighting under a canopy. The two-story home provides large windows that reflect the evening sky, and lush trees frame the property, creating a serene atmosphere.
Cottage in Trent Lakes
4.99 out of 5 average rating, 142 reviews

Lux-5 Bdrm-Waterfront+Hot Tub+Sauna+Game Rm+SUP's+

Direct waterfront cottage is perfect for multi family getaway. Situated directly on 160 ft of waterfront on Buckhorn Lake with endless fun. Boasting a hot tub, sauna, 30 ft upper deck with glass rail lighting up BLUE at night, beach volleyball, beach area for little ones, master bdrm walkout to deck & breathtaking water views from EVERY bedroom! For the kids and adults alike there is a ping pong table, foosball, pool table, poker table, pac-man arcade, 4 kayaks, 2 SUP, and paddleboat to enjoy!

Top guest favorite
A wooden dock extends into a calm lake, reflecting fluffy white clouds and blue skies. Lush greenery is visible along the shoreline, creating a serene natural backdrop.
Cottage in Kawartha Lakes
4.93 out of 5 average rating, 196 reviews

Ke's Rustic Retreat in Kawartha Lakes

WELCOME TO KE’S PLACE! This ALL SEASONS rustic, private, 4 season, lakefront cottage on Pigeon Lake features 3 bedrooms, 3 full/double sized beds, large bright living room with sleeper sectional, newly renovated kitchen, two large decks, private dock, indoor fireplace, enclosed patio room, outdoor fire pit, and large yard for games and more. 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.

Top guest favorite
Cottage in Trent Lakes
4.99 out of 5 average rating, 167 reviews

Panoramic Lake Views Inside & Out, Cozy & Relaxing

Enjoy panoramic views of Lower Buckhorn Lake with the family! Relax perched in the hot tub atop the rocks of the Canadian Shield, nestled among the tall pines. This newly updated waterfront cottage features 3 bedrooms & an open concept living space. Over 280 feet of waterfront for you to enjoy the sunrise & sunsets & fish off the dock! Get cozy on the couch, play games, or watch movies. Take a stroll around the island. Hi speed Wi-fi to work or play. 6 minutes to town, less than 2 hrs from GTA.

Top guest favorite
A spacious hot tub overlooks the Severn River, surrounded by greenery. Chairs are positioned nearby on the grassy lawn, providing a relaxing space to enjoy the water views and sunshine. The calming river scene features boats gently cruising by, enhancing the outdoor experience.
Cottage in Severn Bridge
4.95 out of 5 average rating, 173 reviews

CARL in Muskoka: Waterfront Cottage with Hot Tub

Enjoy your own piece of Muskoka in this beautiful waterfront cottage! Only 90 minutes from Toronto nestled away on a private road along the Severn River sits CARL. Not a man... but a way of life. The Cottage and River Life! CARL is your retreat from the city, perfect for getting out in nature and experiencing everything life on the water has to offer. Whether you enjoy swimming, kayaking, great fishing or just relaxing on the dock or in the hot tub taking in the views... we've got you covered.

Guest favorite
Cottage in Georgina
4.95 out of 5 average rating, 133 reviews

Resort-Style Luxury Waterfront Cottage

Experience luxury at our 5-star, Superhost-rated waterfront cottage on Lake Simcoe, just 80 KM from Toronto! A guest favorite, it offers breathtaking sunsets and sunrises from the living room and loft. Relax on the sandy beach with waist-deep waters, and enjoy the patio, BBQ, bar, lounge, kayaking, and fishing. With a fully equipped kitchen, 3 bedrooms, and 2 bathrooms, it comfortably accommodates up to 8 guests. Book your dream getaway today for the perfect blend of relaxation and adventure!

Guest favorite
A wooden dock extends over the calm water, adorned with two red Adirondack chairs facing the lake. A grassy area is visible with seating and a tree providing shade. The cottage can be seen in the background under a clear blue sky, enhancing the outdoor setting.
Cottage in Kawartha Lakes
4.86 out of 5 average rating, 141 reviews

Little Blue Lakefront Cottage on Sturgeon Lake!!

Beautiful waterfront cottage on Sturgeon Lake. Super spacious feel w/ 2 BR to sleep up to 5.Gourmet kitchen w/ high end appl, large dining table sits 6. Relax & BBQ on comfortable deck w/ beautiful lake views and table to seat 6. Enjoy the fire-pit on the Muskoka Chairs. Important Note: Dock is usually ready for first week of May every year. Could be earlier depending on the weather. Also the City of Kawartha Lakes has a NO BONFIRE ban during April each year. So please do not do a BONFIRE.

Top guest favorite
Cottage in Cobourg
4.98 out of 5 average rating, 364 reviews

Couples Forest Retreat: Hot Tub, Sauna, Fireplace

Escape to a historic estate wellness retreat. Described by Narcity Canada as “Like Living in the Holiday” Praised as a couple's getaway, near Ste. Anne's Spa. Follow us @coachhouse_cobourg Step into a 150-year-old coach house nestled on a stunning 5-acre Victorian estate. This beautifully restored guest house combines historic charm with modern comforts, offering a private hot tub, sauna, a cozy fireplace, and a serene escape minutes from Cobourg’s vibrant downtown and pristine beaches.

Top guest favorite
Cottage in Cameron
4.93 out of 5 average rating, 105 reviews

Lakefront Cottage | 2 BR, Hot Tub, Fire Pit

Welcome to your private Kawartha Lakehouse retreat! This spacious home is the perfect luxury escape for couples, small families, or friends who want extra room to spread out and relax. Enjoy the comfort of a full-size lakehouse with only 2 bedrooms, giving you both privacy and space on the tranquil lakeside. Whether you’re planning a romantic getaway, a family trip with kids, or a work-from-the-lake escape, our home offers a cozy setup with the space and privacy of a full lakehouse.

Top guest favorite
Cottage in Georgina
4.91 out of 5 average rating, 300 reviews

Luxury Lakefront | Sandy Beach, Hot Tub & Dock

Luxury lakefront cottage on beautiful Lake Simcoe with a rare shallow sandy-bottom beach, perfect for swimming and family fun. Relax in the hot tub and enjoy breathtaking sunsets from the private dock. Ideal for family vacations and group getaways near Toronto, just minutes from Hwy 404. Enjoy kayaking, paddleboarding, fishing, BBQ, a fire pit, 6 spacious bedrooms, 4 bathrooms, chef's kitchen, and a bright open-concept living area. Peaceful, private, and close to everything you need.

Top guest favorite
Cottage in Gravenhurst
4.92 out of 5 average rating, 173 reviews

Marrakahshe Retreat | Luxury Sauna, Beach & Yurt

Welcome to Marrakahshe Retreat: A curated lakeside experience & sauna under 2-hours from Toronto. With 230 feet of private lakefront, southwestern exposure, stunning views and eclectic high-end decor, this exquisite Muskoka retreat is the perfect place to relax, unwind, and immerse yourself in nature. Enjoy the pristine beauty of Kahshe Lake and the Canadian Shield, along with your very own 50 ft. walk-in sandy beach, glamping yurt, dock, sauna, fire pits, home theatre and more.

Superhost
A wooden deck features a circular hot tub surrounded by fall foliage. Adironack chairs sit under a sunlit pergola, overlooking the serene river. Kayaks are visible in the background, creating a cozy atmosphere for relaxation.
Cottage in Minden
4.89 out of 5 average rating, 105 reviews

Hills Haven - Luxury Riverfront Cottage

Welcome to Hills Haven! This peaceful 2 bedroom four-season cottage is located on Irondale River and is the perfect spot for nature enthusiasts to relax and unwind! • 2 bedrooms - sleeps 4 • Hot tub • Starlink fast speed WIFI • River view • Swimming Friendly • BBQ • 2 Kayaks • Fire Pit • Wood Stove • Screened in sunroom • Smart TV • Fully equipped kitchen • Board Games • EV charger • Heating/Air Conditioning • Pet Friendly For more info follow us on IG at @hillshaven_minden

Guest favorite
A spacious living room features a high wooden ceiling with a ceiling fan and large windows allowing natural light to fill the space. Comfortable seating is arranged around a central coffee table, complemented by a wood stove. Books and games are displayed on a nearby shelf.
Cottage in Kawartha Lakes
4.87 out of 5 average rating, 174 reviews

Year-Round Relaxation, a Modern Riverfront Cottage

Welcome to Somerville Lodge, a thoughtfully designed cottage with all the modern amenities you need to make the most of your relaxing getaway In Kawartha Lakes, under 2.5 hours from Toronto, our cottage sits on an acre of land along 350ft of the Burnt River, perfect for swimming, kayaking and paddle boarding. A large deck has space for lounging, or relax in the hot tub. The large living room, dining room and kitchen give plenty of space for any family or group. STR2026-178

Popular amenities for Oakwood cottage rentals