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Holiday Homes in Jackson's Point

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    Don't let other travellers get your favourite Jackson's Point area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 24 Rentals in Jackson's Point
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    Lake Simcoe-- Jacksons Pt1 / 13
    (1)Excellent
    Jackson's Point
    6 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Jackson's Point
    3 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    Jackson's Point
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    The following rentals are within 25 kilometres of Jackson's Point.
    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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    • 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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    L0K 1A0, Beaverton, Ontario
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Shanty Bay, Ontario 2br - Carriage Ridge/Hills1 / 15
    (5)Very good
    Shanty Bay, Canada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Mountain Views
    • Air Conditioning
    • Hot Tub
    • Shared Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 September 2015
    From the accommodations to the many activities, both planned and impromptu, this resort was ideal for a week's getaway. Something for everyone. Even had a complimentary...
    Reviewed 26 September 2015
    My wife and I like to come here for a few weeks in mid September after the summer rush is over and children are back in school. The leaves are starting to turn making for...
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    About this property
    This 2br/2ba lockoff suite is fully furnished with a full kitchen, living room with sofa sleeper, fireplace, king size bed in master bedroom with jacuzzi tub, 2nd bedroom with king size bed & kitchenette, stacked washer/dryer & patio/balcony. 1,200 square feet suite sleeps up to eight guests....
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    L0L 2L0, Shanty Bay, Oro Station
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Waterfront Vacation Property North of Toronto1 / 19
    (1)Excellent
    Beaverton, Canada
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Central Heating
    • Ocean Views
    • Patio
    • Wi-Fi
    • DVD Player
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 August 2016
    We had a great time up at the cottage! Lots of room for 7 kids to play and tons of toys and things to do! The weather wasn't the greatest but the owner was kind enough to extend...
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    About this property
    Beautiful Waterfront (Lake Simcoe) Vacation Home. Spacious (2150 sq ft), two level, extensively renovated, modern home. Comfortably sleeps 8-10. Extensive renovations include new flooring throughout home, freshly painted exterior & interior, stainless steel appliances in kitchen, enormous...
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    L0K 1A0, Beaverton, Ontario
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    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
    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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    L4P 3C8, Keswick, Georgina
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    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
    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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    L0E 1S0, Sutton, Georgina
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 18
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    Keswick
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • 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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    L4P 1K6, Keswick, Georgina
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Keswick
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Waterfront
    • Wi-Fi
    • Central Heating
    • Grill
    • Washer
    • Patio
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It's 4 spacious bedrooms Luxury modern house, newly renovated. It's able to view amazing Sunset on Lake Simcoe from any floor. It's located in community of Keswick, east side of Cook's bay, just 45 mins drive from Toronto. It's nearby Restaurants, Groceries, stores, golf course, public dock, parks,...
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    L4P 3C8, Keswick, Georgina
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    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
    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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    L0L 2L0, Shanty Bay, Oro Station
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beaverton, Canada
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    K0M 1B0, Beaverton, Ontario
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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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 7 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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    L4P 3E9, Keswick, Georgina
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Shanty Bay, Canada
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • 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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    L0L 2L0, Shanty Bay, Oro Station
    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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    • 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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    L0L1T0, Shanty Bay, Oro Station
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Keswick
    6 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is one Beautiful Cottage by one of Ontario's biggest Lake Simcoe (Cook's Bay). Lot's to do here with Friends and Family. Fishing, Boating, Beach, Out Door BBQ on a Huge Lake Side Private Property are just a few things to mention. Beautiful Fireplace to sit by and read in Peace or have a...
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    L4P 3C8, Keswick, Georgina
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 12
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    Shanty Bay, Canada
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • 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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    L9S, Shanty Bay, Oro Station
    Holiday Rental House - 4 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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    L9P 1R4, Zephyr, Uxbridge
    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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    • 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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    L0E, Sutton, Georgina
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Keswick
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Washer
    • Wi-Fi
    • Central Heating
    • Housekeeping Included
    • Grill
    • Cable/satellite TV
    • Patio
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly opened in July 2016. fully renovated Lake Simcoe cottage, only 35 minutes drive from Toronto( easy commute via 404)..Direct waterfront huge 100'X260' lot, sutable for a large group up to 13 people. south-west exposure, unrivaled sunset. Famous ice-fishing area-cook's bay. lots of winter lake...
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    L4P 3T6, Keswick, Georgina
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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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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    L0E 1L0, Sutton, Georgina
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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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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    • Balcony
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Patio
    • DVD Player
    • Shared Indoor Pool
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 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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    L0L 2L0, Shanty Bay, Oro Station
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    L0L 2L0, Shanty Bay, Oro Station
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    L0E, Sutton, Georgina
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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