Holiday rentals in Oakwood

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Top-rated holiday rentals in Oakwood

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Guest favourite
A spacious glamping dome is nestled among lush green trees, showcasing large windows and a triangular design. The entrance is framed by rustic outdoor seating, and soft lighting emanates from inside, creating an inviting atmosphere amidst the surrounding foliage.
Dome in Utopia
4.95 out of 5 average rating, 271 reviews

Off-grid Glamping Dome Nestled in the Woods

Welcome to our private campsite in Utopia, ON. Our family’s glamping dome is your chance to experience a unique getaway surrounded by the sights & sounds of nature. Amenities include camping essentials & some glamping perks: king size bed, bbq, fireplace, Indoor incineration toilet, soap & water, outdoor shower (summer only), kettle, cooking utensils. Nearby is Purple Hill Lavender Farms, Drysdale's Tree Farm, Tiffin Conservation Area, Nottawasaga & golf courses. Wasaga Beach is 30 min away.

Top guest favourite
The tiny home features a covered deck with a red umbrella, offering outdoor seating for relaxation. Lush green grass surrounds the structure, enhancing the sense of privacy. Large windows provide natural light, complementing the modern black exterior.
Tiny home in Beaverton
4.99 out of 5 average rating, 133 reviews

Riches Retreat-Tiny Home

Beautiful newly built Tiny Home on a large part of private property with its own driveway & parking. Very secluded with large yard in front, hosting many type of birds, squirrels and rabbits to watch. Perfect setting & space to have a peaceful, relaxing getaway. You'll have a feel of privacy & be comfortable. Great place to unwind, have fun or even catch up on work with no distractions! Well equipped kitchen for cooking & BBQ on deck. Parking for 3 vehicles plus space with a small/med trailer.

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
4.86 out of 5 average rating, 133 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.

Guest favourite
A lakefront cottage is set on a grassy area beside the water, featuring a wooden dock extending toward the lake. The exterior shows a welcoming porch and surrounding trees provide shade. Stone borders accentuate the shoreline, creating a natural beach-like atmosphere.
Cabin in Nestleton Station
4.92 out of 5 average rating, 200 reviews

Cozy, Quirky and Modern Lakefront Cottage

Welcome to the Scugog Sugar Shack! Just 70 mins away from Toronto, escape to enjoy picturesque sunsets at this cozy lakefront cottage nestled under the largest collection of mature sugar maples on Scugog Point. This 2 bedroom open concept 1940s cottage has been updated with all the creature comforts while staying true to its quirky roots. With private access to Lake Scugog, known for fishing, kayaking, paddle boarding and swimming, bask in the sun all day & sit by a fire under the stars.

Top guest favourite
Cottage in Cobourg
4.98 out of 5 average rating, 357 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 favourite
A spacious living area features a variety of seating options, including a cozy couch and rocking chairs. Large windows allow natural light to enter, illuminating the lush indoor plants. Decorative rugs and artwork add character to the eclectic decor, creating a relaxed atmosphere.
Farm stay in Uxbridge
4.98 out of 5 average rating, 329 reviews

Private Loft w Sauna, Fireplace, Wi-Fi & Projector

Welcome to the LOFT - A private, eclectically designed spa-inspired unique stay in the historic Webb Schoolhouse, less than an hour from Toronto. Featured in TORONTO LIFE, this private loft includes your own sauna, unique hanging bed, wood stove, kitchenette and is filled with art, and huge tropical plants as well as a projector & giant screen for epic movie nights. Relax and recharge, roam the grounds and enjoy the beautiful outdoor spaces, the permaculture farm, animals, and fire pit.

Top guest favourite
An aerial view captures the cabin nestled among vibrant autumn trees by the serene lake. Lush green fields stretch into the distance, while the water reflects the surrounding landscape, creating a peaceful atmosphere that invites relaxation and connection with nature.
Cabin in Hastings
5 out of 5 average rating, 116 reviews

Perfect City Escape! Off-Grid Waterfront Cabin

Get off grid and disconnect to reconnect at our luxurious and exclusive spring fed lake waterfront cabin. Forest bathe in the sounds of nature while relaxing on the porch or on your private dock. Please note cabin is COMPLETELY OFF GRID. NO RUNNING WATER, NO SHOWER. Endless potable water is provided for cooking and drinking. Solar generator and battery powered lanterns throughout the cabin for light at night. Pretty and modern outside bathroom (outhouse) located steps from cabin.

Top guest favourite
The image captures a serene lake at sunset, reflecting vibrant hues of orange and purple in the sky and water. A wooden dock extends into the calm water, providing a tranquil setting for evening activities.
Guest house in Port Perry
5 out of 5 average rating, 148 reviews

Lakeside Guest Suite, on Lake Scugog, Port Perry

WATERFRONT PROPERTY….Enjoy stunning sunsets from the basement walkout guest suite. Take in views from the living room, bedroom (queen bed), or large 34 foot long private patio! The backyard leads directly to the lake including a fire pit for your use. Please note that the natural slope of the yard (40 stairs) may not be suitable for those with mobility issues. While the suite doesn't feature a kitchen, Port Perry is only an 8 min drive and offers many culinary options.

Guest favourite
The geodesic dome features a modern white exterior, set against a backdrop of trees. A wooden deck extends from the dome, leading to a covered gazebo, with a pathway of wood chips guiding the approach. Soft sunlight filters through the branches, creating a serene atmosphere.
Dome in Uxbridge
4.86 out of 5 average rating, 119 reviews

The Bubble Glamping Dome

Escape to a luxury geodesic dome on our scenic farm, nestled at the edge of the forest. Fully equipped with heating, cooling, a private washroom, deck, and hot tub, it’s the perfect blend of comfort and nature. Explore the farm, meet our sheep, chickens, and livestock guardian dog, or hike over 100 acres of connected regional forest. Whether you’re relaxing under the stars or adventuring outdoors, this unique glamping retreat promises an unforgettable experience.

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, 105 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 of a timber-frame cabin is framed by tall evergreen trees. A large window reflects the surrounding foliage, and warm lights are strung along the wooden facade. The design showcases a blend of natural materials and architectural lines.
Cabin in Lakefield
4.95 out of 5 average rating, 546 reviews

The Nook, Peaceful Retreat: Lake+Hot Tub+ Sauna!

Heritage barn turned zen-den! Our open-concept, loft style, timber-frame cabin has exposed beams, barn board walls, and plenty of windows to enjoy the lake view. Decorated with a beachy boho meets mid-century vibe, it's cozy and airy at the same time! The private deck offers the perfect place to listen to the birds and read a good book. The Nook is on our 1 acre, lakefront property, alongside our home. We hope you love it here as much as we do!

Guest favourite
An outdoor fire pit surrounded by gravel is present, featuring two wooden chairs. A hot tub is located nearby, positioned in front of a geodesic dome with large windows. String lights are draped overhead, illuminating the outdoor space.
Dome in Utopia
4.96 out of 5 average rating, 185 reviews

Glamping Dome Riverview Utopia

Come retreat into nature at the Riverview Glamping Dome… a 4 season getaway located on Rustic Roots Farm and Eco-retreat 1 hour north of Toronto. Whether you're looking for a romantic getaway or to come disconnect from the hustle and bustle of everyday life this geodesic dome is for you! Located on 64 sprawling acres come explore hiking trails, go fishing, relax in the hot tub, and stargaze fireside.

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