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Jacksons Point Holiday Homes

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    Don't let other travellers get your favourite Jacksons Point area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 21 Rentals in Jacksons Point
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    Lake Simcoe-- Jacksons Pt1 / 13
    (1)Excellent
    Jacksons Point
    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Jacksons Point
    4 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    Jacksons Point
    3 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    Jacksons Point
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Poplar Hill 'Guesthouse' is situated on a beautiful equestrian property just north of Toronto. Located in Udora, a small peaceful Hamlet, this country house is perfectly nestled in Ontario's farm country. In less than five minutes you can be at the several local farms picking strawberries or...
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    Location Information
    Jacksons Point, Georgina L0E 1N0
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    The following rentals are within 25 kilometres of Jacksons Point.
    Exquisite Executive Cottage on Lake Simcoe1 / 23
    (5)Excellent
    Keswick
    4 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Grill
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 May 2017
    This was our second time here at this wonderful home and it was the same as last time...amazing. The place is abundantly stocked with supplies, kitchen utensils and sheets and...
    Reviewed 30 April 2017
    A group of us rented this cottage for a weekend and it was one of the most enjoyable experiences we have had. The location is stunning, the pictures do not do it justice and the...
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    About this property
    This home is spacious, elegant, and finished top to bottom with all the amenities. Private indirect lakefront, on lake approx 19 x 16 miles wide. Gradual entry is perfect for children. Gourmet kitchen with cathedral ceilings, numerous walkouts. Each bedroom has own ensuite bath. All the...
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    Keswick, Georgina L4P 3E9
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 14
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    Carriage Hills Resort Two-Bedroom Suite1 / 14
    (1)Excellent
    Shanty Bay, Canada
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
    • Internet Access
    • Grill
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 March 2018
    We came here for the 2nd year in a row, but this time with more people. This place is great for families. Close to Moonstone to ski, and 20 mins to Barrie. The rooms are large...
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    About this property
    Two-Bedroom Suite (one bedroom and a separate studio) sleeps up to 8 people. Approximately 1,200 square feet. One bedroom includes a bedroom with a king size bed with a Jacuzzi bathroom, separate shower, living room with a queen size pull out sofa bed, dining area, fully equipped kitchen, fireplace...
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    Shanty Bay, Oro Station L0L 2L0
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cozy cottage serenely nestled between Talbot River and the Trent-Severn Waterway1 / 19
    (2)Excellent
    Beaverton, Canada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Terrace
    • Grill
    • Parking
    • Washer
    • Balcony
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2017
    The cabin is on a great size acre of land which, allows you to play any number of sports to keep you entertain. It's small and cozy and yet, just enough space to make you feel...
    Reviewed 24 July 2017
    This was a great find. My wife, son and I needed to pick our daughter up very early from a nearby camp, so we decided we would make a weekend of it. We found this place and it...
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    About this property
    This serene cottage is tucked away on a 4 acre private park steps from the Talbot River and just across from the Trent-Severn Waterway. Newly renovated with all the comforts of home, including dishwasher, washer/dryer, full stove and oven, microwave, keurig machine and central vac. A canoe and...
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    Beaverton, Ontario L0K 1A0
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Georgina Lakeshore Vacation Home1 / 16
    (1)Excellent
    Keswick
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Secure Parking
    • Private Garden
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Waterfront
    • Washer
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2018
    Great location! House is beautiful and has everything you need to enjoy your stay. Our family had a wonderful time. Would definitely book this house again. Thanks Michael
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    About this property
    Secluded Tucked Away beautiful Guesthouse in Cook's Bay. Minutes to Lake Simcoe. The Modern Kitchen Features Granite Counters, S/S Appliances, Backsplash and Ceramic Tile Floor. Entertain In The Formal Dining Room Which Boasts Hardwood Floors, Crown Moulding and French Doors. The Generous Family...
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    Keswick, Georgina L4P 3C8
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Shanty Bay, Canada
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two-Bedroom Suite (one bedroom and a separate studio) sleeps up to 8 people. Approximately 1,200 square feet. One bedroom includes a bedroom with a king size bed with a Jacuzzi bathroom, separate shower, living room with a queen size pull out sofa bed, dining area, fully equipped kitchen,...
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    Shanty Bay, Oro Station L0L 2L0
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    Shanty Bay, Canada
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Garden
    • Waterfront
    • Wi-Fi
    • Secure Parking
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Executive family cottage, Extra clean , Professionally landscaped , Outdoor patio furniture ,Gazebo with mosquito netting & lighting, Water treatment system, Backup electricity generator, All brand new furniture , Sleeps 8 people Boat house at shoreline, Security system, Wifi high speed internet...
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    Shanty Bay, Oro Station L0L1T0
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Charlotte's Cottage-Lake Simcoe1 / 35
    (4)Excellent
    Keswick
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Patio
    • Wi-Fi
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 October 2017
    Very comfortable cottage in a great location. All amenities provided.I would recommend the cottage to anyone wishing a quiet family get away
    Reviewed 19 July 2016
    Pristine two-bedroom winterized cottage sitting on a quarter acre includes wifi. Beautiful remodeled serving kitchen with dishwasher, laundry and dryer. Adjacent prep area keeps...
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    About this property
    Charlotte's Cottage is located in Island Grove in the township of Georgina, Ontario, on the south shore of Lake Simcoe. It is between the towns of Sutton and Keswick. It is a 10 minute drive to each town. Charlotte's Cottage has private access to Lake Simcoe with a small dock, a boathouse, and...
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    Location Information
    Keswick, Georgina L4P 3E9
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Shanty Bay, Canada
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Lake Simcoe region is a favourite year-round holiday destination with many area events and attractions. This Lake Simcoe waterfront cottage is located at prestigious Big Bay Point a short drive from downtown Barrie and just 45 minutes from the Greater Toronto Area (GTA). The 2200 square foot...
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    Shanty Bay, Oro Station L9S
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Guest House by Franklin Beach1 / 10
    (1)Very good
    Sutton
    4 Bedrooms, 2 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Secure Parking
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 July 2018
    The pictures do not do it justice, the house is in great condition. The only reason I didn't give it 5 stars is because the beach isn't walking distance, we had to drive to the...
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    About this property
    This place resides in a quiet area near Franklin Beach which is 5 minutes walking distance. There is a huge playground by the beach. It is a very convenient place, as there are many stores nearby such as No Frills, Tim Hortons, LCBO etc. There is also a bus stop 1 minute away from this house. It is...
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    Sutton, Georgina L0E 1S0
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 18
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    Beaverton, Canada
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Washer
    • Internet Access
    • Grill
    • Parking
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    87 Paradise Road, Bolsover. Brand new cottage. Can accommodate 6 grown up and 3 kids. Brand new cottage, built by Viceroy, lake front at Canal lake. 4 bedrooms. Can accommodate 6 grown up people and 3 kids. Air conditioning, walk out basement. On the lot there is shed with generator, boathouse as...
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    Beaverton, Ontario K0M 1B0
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Carriage Hills Resort Fabulous 2 br sleep81 / 9
    (1)Excellent
    Shanty Bay, Canada
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Patio
    • DVD Player
    • Shared Indoor Pool
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 December 2016
    The staff were very pleasant and helpful. The unit itself was amazing, clean, wonderful atmosphere, and everything you will need for a weekend or a week was included and in...
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    About this property
    Surrounded by Canada's scenic Horseshoe Valley, Carriage Hills Resort is an all season retreat into a world where nature's beauty provides the perfect backdrop for relaxation and recreation. Enjoy the recreational abundance offered in the area. Go for a swim in our indoor/outdoor pool or play...
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    Shanty Bay, Oro Station L0L 2L0
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Zephyr, Canada
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    5 bedroom log cabin located in a rural setting, surrounded by an area of horse ranches, nature forest, Golf course and ski resorts. This cottage is best suited for adults looking for a private retreat. The log cabin is hidden in 10 acres heavy woods. It's a perfect place for people who want their...
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    Zephyr, Uxbridge L9P 1R4
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Sutton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Housekeeping Included
    • Air Conditioning
    • Private Garden
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is a private residence on the shore Lake Simcoe mid-way between Jackson's Point and Sibbald Point Provincial Park. We have two newly decorated rooms - The Birch Room and the Forest Room - and, have recently started providing winter B & B services for ice fishing parties. If you need an...
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    Sutton, Georgina L0E
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Keswick
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • Grill
    • Patio
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New 3 Bedroom Beautiful Fully Detached Home Conveniently Located in Keswick. Family Size Kitchen, Bright Open Concept Living Room With 9 Ft. Ceilings。 3 bedrooms (king; double; single, + extra double or single mattress) fully equipped kitchen microwave convection oven dishwasher coffee machine...
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    Keswick, Georgina L4P 1K6
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Shanty Bay, Canada
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    One bedroom with A/C, heating, Alarm clock, kitchenette, including refrigerator, stove, microwave,Hair dryer.Sofa beds for extra guests,TV,Washer and dryer,Wireless internet access.family escape into Ontario's Lake Country, with endless activities, ongoing events and limitless opportunities to have...
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    Shanty Bay, Oro Station L0L 2L0
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Sutton
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Grill
    • Central Heating
    • Balcony
    • Patio
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 September 2014
    Nice house a bit messy, adorable dogs. No soap no towel in the bathroom. When we ask what time the breakfast she states if you want breakfast they have lots of nice places around!
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    About this property
    Charming turn of the Century cottage on the shores of Lake Simcoe. 45 Min from Toronto, yet like a world away. 1 Room is a semi-detached with en-suite and private gardens and deck. Like a Motel Room. This would be the room you would book for $130.00 for two people. 2nd room in the Master...
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    Sutton, Georgina L0E 1L0
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    Sutton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Patio
    • Wi-Fi
    • Secure Parking
    • Cable/satellite TV
    • Private Garden
    • Housekeeping Included
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our home is a private residence on the shore Lake Simcoe mid-way between Jackson's Point and Sibbald Point Provincial Park. We provide bed and breakfast year round. We have two newly decorated rooms - The Birch Room and the Forest Room - - and, have recently started providing winter B & B services...
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    Location Information
    Sutton, Georgina L0E
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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