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Cottage holiday rentals in Oakwood

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Oakwood

Guests agree: These cottages are highly rated for location, cleanliness and more.

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Guest favourite
Large glass patio doors frame a scenic view of the waterfront, revealing a private deck with seating and a hot tub surrounded by trees. Sunlight casts a warm glow over the area, enhancing the sense of tranquility.
Cottage in Innisfil
4.89 out of 5 average rating, 207 reviews

Stunning Lakefront Cottage Hot Tub & Sauna

.🧘 Relaxing, Quiet, waterfront property with stunning nature. 🧖‍♀️ Experience a private Spa with year round new sauna & new hot tub and amazing view. Please bring your own bath towels! 🤫 A peaceful oasis for families. Please describe your family before requesting to book. Max 6 guests incl children. Absolutely no events, parties, noise allowed. Not for a group of friends 🏖50’x302’ lot, private dock, gazebo 👩🏻‍💻65” smart 4K UHD TV, fast / reliable internet, LCD fridge, filtered water

Guest favourite
Cottage in Harcourt
4.93 out of 5 average rating, 151 reviews

Lakefield Lakehouse /Hot Tub/ Sauna/ Games Garage

Unwind at this private, pet-friendly, all-season lakefront cottage with 4 bedrooms and 2 full bathrooms—ideal for families or small groups looking for a relaxing getaway. Just 5 mins from Lakefield’s shops, cafes, spas & a local chocolate factory. Thoughtfully designed & fully stocked for a cozy, carefree getaway. Sauna is wood burning to use start a fire in chamber and let burn for 30 minutes Hot Tub added May 2025 (up to 7 ppl) We only accept bookings from guests with positive Airbnb reviews

Top Guest favourite
A circular patio area features a fire pit at the center, surrounded by eight colorful Muskoka chairs in red and blue. The setting overlooks a serene lake and wooden dock, with a guitar resting nearby on the lawn, framed by a clear blue sky and scattered clouds.
Cottage in Georgina
4.91 out of 5 average rating, 295 reviews

Luxury Waterfront Cottage Hot Tub & Amazing Sunset

Private lakefront cottage on Lake Simcoe with hot tub, stunning sunset views, and a rare shallow sandy-bottom waterfront — a unique feature rarely found on the lake. Perfect for large families and group getaways near Toronto, just minutes from Hwy 404. Enjoy swimming, kayaking, paddleboarding, fishing, BBQ, fire pit, and a private dock. Features 6 bedrooms, 4 bathrooms, a chef’s kitchen, and spacious open-concept living. Close to town, yet private, peaceful, and perfect for waterfront getaways.

Top Guest favourite
Cottage in Cobourg
4.98 out of 5 average rating, 354 reviews

Forest Retreat: Couples Escape w Hot Tub Fireplace

Slow mornings. Forest surround. Soak under the stars. 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, a cozy fireplace, and a serene escape minutes from Cobourg’s vibrant downtown and pristine beaches.

Guest favourite
Cottage in Georgina
4.95 out of 5 average rating, 125 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 favourite
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
4.85 out of 5 average rating, 131 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 favourite
The property features a spacious lawn bordered by trees, with a rustic cottage visible in the background. A 500 sq ft dock extends into the lake, equipped with seating. A fire pit area is set up on the grassy shoreline, inviting relaxation and outdoor gatherings.
Cottage in Minden
4.92 out of 5 average rating, 291 reviews

Lakefront Cottage Getaway | Hot Tub · Dog Friendly

Relax and unwind at South Lake! Located less than 10 minutes away from the town of Minden, you'll love swimming off the 500 sq ft dock, exploring by canoe and kayak, all the best lawn games, stunning sunsets from the new fire pit, and a sky full of constellations. Perfect for families or friends to enjoy all of the comforts of a modern cottage without missing rustic charm. Cozy up by the propane fireplace and play board games or watch movies. High-speed internet is remote work-friendly!

Top Guest favourite
The living area features a plush blue sofa paired with a modern coffee table, creating a comfortable seating arrangement. Large windows offer views of the lake, allowing natural light to fill the space. Simple decor elements enhance the inviting environment.
Cottage in Sebright
4.93 out of 5 average rating, 106 reviews

Private Lakefront Cottage | Fishing, Canoe & Sauna

Wake up to sparkling Lake Dalrymple views at our private lakefront cottage, just 1.5 hours from Toronto ☀️🌊 Swim, canoe, fish from the dock, BBQ, or relax by the water. After a lake day, enjoy the outdoor barrel sauna 🧖‍♂️ or gather by the lakeside firepit 🔥 for sunsets, s’mores, and stargazing ✨ Inside features AC, a full kitchen, Netflix, games, record player, and stunning lake views. Perfect for couples & families seeking a fun, relaxing summer escape.

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, 102 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 exterior view of the cottage showcases a stone facade illuminated by string lights as twilight approaches. A welcoming deck area features seating for relaxation, while natural surroundings provide a tranquil atmosphere. Steps lead down to the path, enhancing accessibility to nature.
Cottage in Havelock
4.92 out of 5 average rating, 120 reviews

Rowan Cottage Co. on Oak Lake

Nestled among the trees, you’ll find Rowan Cottage Co. on Oak Lake—just 2 hours from the GTA and 3 hours from Ottawa. This newly renovated, design-forward cottage is thoughtfully curated and surrounded by nature, with modern amenities that make it feel like home. The interior, decks, and dock all enjoy southeastern exposure, filling the space with natural light and offering beautiful views across 125 feet of lake frontage on a semi-private lake.

Guest favourite
The tranquil Irondale River is visible, reflecting the soft hues of dawn. Mist rises from the water, surrounded by wooded banks and grassy areas. Trees line the river's edge, enhancing the serene landscape. A serene ambiance is created as the morning light emerges.
Cottage in Gooderham
4.87 out of 5 average rating, 188 reviews

Luxury Four-Season Riverside Cabin

Four-season cottage, on the Irondale River. Enjoy luxuries such as heated bathroom floors, soaker tub, modern kitchen, washer/dryer. The high ceilings and windows allow nature in. Step out to paradise, relax by the campfire, paddle or swim the river. Three bedrooms: King, queen, double, plus 2 Bean Bag chairs that convert into mattresses. Perfect for families or romantic getaways. Comfortably sleeps 6 guests. NEW- STARLINK INTERNET!!

Top Guest favourite
A wooden dock extends over still water, featuring two red Adirondack chairs positioned for lakeside relaxation. Surrounding greenery includes a large tree and shrubs, with the cottage visible in the background, creating a serene outdoor setting.
Cottage in North Kawartha
4.93 out of 5 average rating, 204 reviews

South Bay Waterfront - Pet Friendly, With hot tub

Check out this gorgeous newly renovated 3 bed 2 full bath lake front cottage located in the heart of Lakefield cottage country! It's a perfect getaway for family and friends to enjoy! This property is facing upper stony lake perfect for fishing, kayaking and canoeing. Equipped with Air Conditioning and Heating, perfect for summer and winter stay! Place is furnished with a fully stocked kitchen, dishwasher, BBQ, onsite laundry, wifi and more!

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