
Holiday houses in Oakwood
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Top-rated holiday rentals in Oakwood
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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...
4.97 out of 5 average rating, 503 reviews
Lakefront Bungalow "Sunrise Bay" Kawartha Lakes
As seen on "Scott's Vacation House Rules". Wake up to a beautiful sunrise at our peaceful all season lakeside retreat! Enjoy views of the lake from the dock, the screen room, the main bedroom and all areas of the main living area. Have fun outdoors on our large property with 120 ft of waterfront or enjoy our expansive indoor living area; featuring ample seating, a games room and a custom built vertical chess board. Watch the moon rise over the lake and stay warm by our large outdoor fire bowl.
4.96 out of 5 average rating, 54 reviews
Lakefront Cottage + Boathouse & Sunsets
Lakefront summers with spectacular sunsets, private dock, and a relaxed boathouse hangout. Spend your days kayaking, paddleboarding, swimming, and fishing, then wind down with evening fires and sunset views over the lake. The cottage is a cozy, comfortable space for easy family lake days, with room to gather, unplug, and enjoy time together. When you feel like exploring, historic downtown Port Perry is just minutes away, along with local wineries, breweries, live music, and day-trip adventures.
5.0 out of 5 average rating, 49 reviews
Royal Beach Lake House & Spa w/ Hot Tub & Sauna
Royal Beach Lakehouse & Spa is your perfect experience of lakeside luxury! Sink your toes into the sand as you relax with your loved ones, our luxury retreat boasts panoramic views of Lake Simcoe! Wake up feeling refreshed after enjoying your private infrared sauna and fun water toys and activities. End your days with a spectacular sunset from your lakeside hot tub & firepit! Our chef's dream kitchen also awaits! This fully equipped lake house is sure to become your next vacation destination!
4.98 out of 5 average rating, 46 reviews
Private Waterfront Cottage at Lake Simcoe
Luxurious and spacious private waterfront cottage at Lake Simcoe. Enjoy stunning lake and sunset views. An hour from Toronto, this newly renovated cottage offers a fully equipped kitchen, 5 bedrooms, 3 bathrooms, and a spacious dining and living area. Additionally, beautiful outdoor patio, BBQ grill and private fireplace, perfect for relaxing with friends and family. This cottage offers easy access to a private waterfront to enjoy water based activities such as swimming, boating, and fishing.
4.99 out of 5 average rating, 92 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!
4.96 out of 5 average rating, 145 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.
4.87 out of 5 average rating, 150 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.
4.92 out of 5 average rating, 226 reviews
All Season Indoor Pool Escape
This stunning property has completed a full renovation to offer you the ultimate in luxury living. Our estate property features 4 newly renovated large bedrooms, each with an ensuite bathroom. The indoor pool with floor-to-ceiling windows will be the perfect spot for family fun and relaxation, and the basketball pad and outdoor space backing onto a wheat field will provide plenty of opportunities for outdoor activities. Even when it's cold and raining, the indoor pool is a perfect escape!
4.97 out of 5 average rating, 70 reviews
Lakefront Cottage | 2 BR, Hot Tub, Fire Pit
Welcome to your private Kawartha Lakehouse retreat! This spacious home is the perfect luxury escape for couples, small families, or friends who want extra room to spread out and relax. Enjoy the comfort of a full-size lakehouse with only 2 bedrooms, giving you both privacy and space on the tranquil lakeside. Whether you’re planning a romantic getaway, a family trip with kids, or a work-from-the-lake escape, our home offers a cozy setup with the space and privacy of a full lakehouse.
4.92 out of 5 average rating, 108 reviews
North Geodome - Birchwood Luxury Camping
Located one hour from Toronto, Birchwood is a luxury camping experience for two. Immersed in a private forest on Scugog Island, our geodesic dome allows for a cozy and relaxing getaway. Enjoy the surrounding landscape and check out local shops and restaurants on Port Perry main street. Our geodome is designed for 2 guests however a group 3 adults are welcome. Additional guests must be 12+ and added to your reservation at the time of booking. We do not allow pets.
4.9 out of 5 average rating, 610 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.
4.86 out of 5 average rating, 156 reviewsPopular amenities for Oakwood holiday rentals
Other great holiday rentals in Oakwood

Lake Scugog Waterfront Cottage
5.0 out of 5 average rating, 69 reviews
Stonegate Retreat | Sauna, Fire Pit, Lake Access
5.0 out of 5 average rating, 29 reviews
Serene Lakeview Getaway with Sauna
4.82 out of 5 average rating, 72 reviews
Muskoka Lakefront• Sauna • Fireplace• Chef kitchen
4.99 out of 5 average rating, 87 reviews
Newly Renovated boathouse on Balsalm Lake
5.0 out of 5 average rating, 33 reviews
★ Modern Waterfront Luxury Lakehouse - 60 Min GTA
5.0 out of 5 average rating, 85 reviews
Luxury Waterfront French Chateau for Large Groups!
4.88 out of 5 average rating, 32 reviews
Hemlock Lake House
4.96 out of 5 average rating, 49 reviewsDestinations to explore
- Scarborough Town Center
- Toronto Zoo
- Sheppard–Yonge Station
- Mount St. Louis Moonstone
- York University
- Vaughan Mills
- Pigeon Lake
- Fairview Mall
- Gull Lake
- Lakeridge Ski Resort
- Dagmar Ski Resort
- Casino Rama Resort
- Bluffer's Park Beach
- Toronto PAN AM Sports Centre
- Sibbald Point Provincial Park
- Bass Lake Provincial Park
- Woodbine Station
- Kawartha Highlands Provincial Park
- Centennial Beach
- Sheppard West Station
- North York Centre
- Rouge National Urban Park
- Durham College
- Petroglyphs Provincial Park





