
Holiday houses in Oakwood
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Top-rated holiday rentals in Oakwood
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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.

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!

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.

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.

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.

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.

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.

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. 🏳️🌈

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.

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!

Cozy Cottage in Kawartha Lakes
This cozy cottage will have you enjoying a tranquil experience with plenty of gorgeous views. Sitting on the edge of Lake Scugog. A plethora of opportunities await the adventurous, with trails minutes away. Historical Port Perry and Lindsay for all your dining and shopping experiences. Additionally, there is an amazing casino and an 18 hole golf course conveniently located.

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
Popular amenities for Oakwood holiday rentals
Other great holiday rentals in Oakwood

Royal Beach Lake House & Spa w/ Hot Tub & Sauna

Muskoka Lakefront A-Frame | Sauna + Hot Tub

3 Bedroom House Rental

Escape to the private shores of Lake Ontario!

18 Acres of Summer Fun: Dock, Games Room, River

Tiny Home Farm Stay

Relaxing 2 bedroom cottage w/ sauna and fireplace!

Lake Simcoe 5BR 4BA Sleeps 12 | Heated Shop
Destinations to explore
- Montreal Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Pocono Mountains Holiday rentals
- Island of Montreal Holiday rentals
- Capital District, New York Holiday rentals
- Northeast Ohio Holiday rentals
- Grand River Holiday rentals
- St. Catharines Holiday rentals
- Niagara Falls Holiday rentals
- Toronto Zoo
- Snow Valley Ski Resort
- Mount St. Louis Moonstone
- York University
- Lakeridge Ski Resort
- Sheppard–Yonge Station
- Cobourg Beach
- Pigeon Lake
- Rouge National Urban Park
- Gull Lake
- Dagmar Ski Resort
- Fairview Mall
- Toronto PAN AM Sports Centre
- Burl's Creek Event Grounds
- Aga Khan Museum
- Vaughan Mills
- Casino Rama Resort
- Bluffer's Park Beach
- Centennial Beach
- Woodbine Station
- Canadian Tire Motorsport Park
- Kawartha Highlands Provincial Park
- Ste Anne's Spa
- Balsam Lake Provincial Park





