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Vacation rentals in Oakwood

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Top-rated vacation rentals in Oakwood

Guests agree: these stays are highly rated for location, cleanliness, and more.

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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, 476 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...

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, 270 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
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, 322 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
A serene lakeside view captures the golden hues of sunset over calm waters. Lush trees and foliage frame the scene, while a well-maintained cabin is positioned to the right, providing an inviting presence against the scenic backdrop.
Cabin in Hastings
5 out of 5 average rating, 115 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 tiny house cabin features a rustic wooden exterior, nestled among trees. A raised deck with a small table and chairs is visible at the entrance, inviting guests to enjoy the surrounding forest. Large windows allow natural light to fill the space.
Tiny homes in Millbrook
4.99 out of 5 average rating, 101 reviews

Pinecrest Forest Cabin

Relax in the solitude of the forest and the luxury of a fully-equipped tiny house that sits in a forest connected to trails on conservation lands. Reconnect with each other or yourself during quiet days among the tress and peaceful nights under the stars. Recharge with nature at this unforgettable forest escape from the city. Cyclists, hikers, skiers appreciate the beauty of Millbrook Valley trails accessed directly from the property. Water lovers visit nearby beaches rivers, lakes.

Guest favourite
Home in Little Britain
4.93 out of 5 average rating, 120 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
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.
Guesthouse in Port Perry
5 out of 5 average rating, 147 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
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, 182 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.

Top guest favourite
Guest suite in Grafton
5 out of 5 average rating, 338 reviews

The Eh Frame - Nordic Spa Retreat - Sunset Suite

Welcome to The Eh Frame, a modern luxury A-frame with unforgettable sunsets, and a full spa set up! -Private Nordic spa patio with hot tub, cold plunge & sauna -3 cozy bedrooms with luxe linens -Full kitchen & BBQ for feast nights -Fast Wi-Fi, board games & fire pit for chill time -Close to forest trails & lake Ontario -Book now to soak, relax, & unwind

Top guest favourite
Cabin in Dysart et al
4.97 out of 5 average rating, 111 reviews

Log Cabin on the Hill | Haliburton

Step outside and watch the sunset burn through the hardwoods from your own hilltop in the Haliburton Highlands — and Barnum Creek - 600-acre wilderness reserve is a 20-minute walk from your front door. This genuine hand-hewn log cabin sits on 2.5 private wooded acres, perched on a hilltop, with three-season views of the sunset glowing in the distance.

Top guest favourite
The exterior of the Ontario Northland Railway Caboose 122 is showcased at night, illuminated by exterior lights. The vibrant yellow and blue structure is positioned on a grassy area, with a wooden pathway leading up to it. Surrounding trees are partially visible in the background.
Train in Gravenhurst
4.99 out of 5 average rating, 136 reviews

Side Tracked in Muskoka

Welcome to Side Tracked in Muskoka, Muskoka’s premier railway-themed stay. Step back in time inside a beautifully restored Ontario Northland Railway Caboose No. 122. Thoughtfully designed, the interior pays homage to the caboose’s railway history while complementing Muskoka’s cozy cottage feel.

Guest favourite
A welcoming living space features a warm wooden ceiling and large glass windows, inviting natural light. A modern fireplace offers warmth, while sleek furniture, including a leather sofa and wooden chairs, creates a cozy atmosphere. A circular coffee table is placed at the center.
Home in Kawartha Lakes
4.96 out of 5 average rating, 253 reviews

nortehaus - Nordic and Japanese inspired escape

Nestled above the ground, surrounded by river and trees, nortehaus was designed as a getaway and grounding space, away, but not too far from the city. Drawing from Nordic and Japanese influences, nortehaus honours simplicity, good company, sustainability, and all things hygge.

Popular amenities for Oakwood vacation rentals

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