Holiday rentals in Oakwood

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Top-rated holiday rentals in Oakwood

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Top guest favourite
Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.
Dome in Bradford West Gwillimbury
4.96 out of 5 average rating, 461 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Top guest favourite
An A-frame cabin is set against a backdrop of lush greenery. The exterior features large windows allowing natural light to fill the interior. An outdoor patio area includes stylish seating, a fire pit, and a hot tub, surrounded by landscaped garden beds.
Guest suite in Grafton
5 out of 5 average rating, 126 reviews

The Eh Frame - Nordic Spa Retreat - Daybreak Suite

The Eh Frame is a 3-story, Scandinavian-inspired luxury cabin with two fully separate units: the Sunrise and Sunset Suites. Your group will have exclusive access to the Sunrise Suite (everything shown in the photos), including two bedrooms, a patio, a private spa, and a fire pit. The front unit, Sunset Suite, is a separate rental. A full firewall runs through the center of the home, ensuring privacy and comfort for all guests. Located just minutes away from Whispering Springs and Ste. Annes Spa.

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, 265 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 exterior of the log cabin is showcased during twilight, highlighting a modern hot tub on a gravel patio. Warm lighting illuminates the structure, revealing the rustic wood texture and natural surroundings, creating a serene outdoor space perfect for relaxation.
Cabin in Reaboro
4.88 out of 5 average rating, 404 reviews

Cedar Springs Cabin - A Cozy Hideaway in the Woods

Tucked away between the hills of Reaboro Ontario, this 175+ year old pioneer log cabin has been brought back to life with the comfort of all new modern amenities, while still keeping the rich historic character of its past. The cabin homestead was crafted in 1847, before Canada was a country. With your significant other, family or friends, come cozy up to the fire, soak in the hot tub and enjoy swimming in the spring fed pond. Board games and movies are provided for your entertainment.

Guest favourite
Home in Little Britain
4.92 out of 5 average rating, 113 reviews

Cozy Lakeside Cottage on Lake Scugog

WELCOME TO OUR COZY ALL SEASONS COTTAGE! Private lakefront cottage (north shore of Lake Scugog) 2 bedrooms (1 queen, 1 full/double), 2 bathrooms, large bright sunroom with sleeper sectional. Large newly renovated deck. Beautiful lake view, large private dock, water facing deck with bbq, huge yard for games, bon fires and more. Located approx. 1.5 hours from Toronto, this cottage is the perfect place for couples, families or friends to escape the hustle and bustle, relax and unwind.

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, 306 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 a 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 open living area features a cozy seating arrangement with a blue couch and a rustic wooden island. A spiral staircase ascends to the loft above. Large windows provide natural light, while a wall-mounted TV and a pellet stove enhance the space.
Guest house in Port Perry
4.98 out of 5 average rating, 109 reviews

Port Perry Island Krazee Acres Hobby Farm

Krazee Acres! Private 8-acre hobby farm a short walk to Lake Scugog, with Farm Fresh smells! Rustic Boho accents, Relaxing Soaker tub, walk-in shower, fully equipped kitchen, pellet stove, and air conditioning. Enjoy outdoor wood fires, sunsets and stars year-round. Free Parking for cars, trailers, boats etc. Large patio. BBQ provided. 3KM to the Great Blue Heron Casino, minutes to Historic Downtown Port Perry. Close to trails and Marina/Restaurant, (Seasonal). Relax

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, 138 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.

Top guest favourite
A charming cabin is situated on the edge of a tranquil lake, surrounded by lush greenery. A wooden dock extends over the water, featuring a canoe and a kayak. A pathway leads from the dock to the cabin, offering scenic lakeside access.
Cabin in Bancroft
4.99 out of 5 average rating, 146 reviews

Serenity Now | Private Waterfront Cabin

Bring your cozy socks and your new book. Make the most of winter and book your ultimate winter getaway at Serenity Now cabin. No neighbours, no noise, just peace and quiet. Ideal for couples or solo adventurers seeking peace, nature, and movie nights with an 80" projector. Private trail (4-5km) for those adventurous souls - snowshoeing, and we provide an auger and fishing rods for ice fishing. We’re committed to creating a safe, welcoming space for all. 🏳️‍🌈

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
4.84 out of 5 average rating, 102 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.

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, 539 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!

Top guest favourite
An outdoor hot tub is presented in the foreground, featuring clear blue water and a colorful flotation device. In the background, a geodesic dome is visible, surrounded by greenery and a wooden deck with seating options. Natural light enhances the inviting scene.
Dome in Utopia
4.96 out of 5 average rating, 169 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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