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Orillia Vacation Rentals

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    All 32 Rentals in Orillia
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    Leaning Tree Cottage1 / 34
    (2)Excellent
    Orillia
    3 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    Family Cottage Escape on Lake Couchiching1 / 12
    (1)Excellent
    Orillia
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    EXECUTIVE WATERFRONT ON BASS LAKE ORILLIA -SUMMER!1 / 6
    (1)Very good
    Orillia
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Cottages and Boats to rent1 / 17
    (2)Excellent
    Orillia
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 July 2017
    Me and my family stayed at this resort for a weekend and it was lovely. Very welcoming vibe to the resort. The owner Chris was super helpful and on top of everything. The...
    Reviewed 28 August 2016
    I had a great weekend with my family. It's nice place to spend sometime with family . I will definitely come back again. There is a lot of fun for kids and adults too.
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    About this property
    Hi Everyone We are small informal resort with twenty-two 1,2,3,4 Bedroom self catering cottages with private bathrooms 4 bedroom 4 star (4 pc bathroom,large-very specious living room,3 single 3 double beds, sleeps max 9 people) 3 bedroom 4 star (4pc bathroom,large-very specious living room, 3...
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    Orillia, Ontario L0K 1W0
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Orillia
    7 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Skiing: Property Is In A Ski Resort
    • Air Conditioning
    • Parking
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sometimes with persistence and luck you find a gem for your family vacation in the beauty & convenience of Lake Simcoe and this generously sized 6000 sq ft brand new lakefront home is the place to look! Golf, swim and sail in summer, cross country and downhill skiing in winter plus ice fishing,...
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    Orillia, Ontario L3V 6H1
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 16
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    Orillia
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Grill
    • Wi-Fi
    • DVD Player
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lakeside guest house with loft is a an ideal location close to hiking trails and cycling trails at McRae Provincial Park. For those with a boat, Marina Del Rey is very close. Casino Rama is 15minutes away and all amenities are available in the City of Orillia 20 minutes away. McPhee Bay on...
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    Orillia, Ontario L3V 6H7
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Orillia
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Once you arrive at my home, I will show you around, provide a key, and show you your bedroom and bath. You are welcome to come and go as you please and I will provide you with a key. There is complimentary coffee and tea and you are welcome to use the kitchen. Your bedroom is clean and...
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    Orillia, Ontario L3V 0E2
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Orillia
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Being built in 2017 and ready for occupancy by May 2018, this seven bedroom lakeside home has everything you could possibly want for your vacation! Photos to come as the project evolves! Perfect for families. Serenity  is located on Lake Simcoe just an hour and a half from Toronto! Tthis new...
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    Orillia, Ontario L3V 0K2
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    Orillia
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Parking
    • Washer
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Searching for the perfect Lake Simcoe cottage rental? This gorgeous newly built 6+ bedroom home offers you all the wonders of lake living without compromising on luxury. Located on the western shores of Lake Simcoe,  just 15 minutes to Orillia with it's Saturday morning farmers market and active...
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    Location Information
    Orillia, Ontario L3V 0K2
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    The following rentals are within 25 kilometres of Orillia.
    Oak Ridge Retreat.  Snow mobiles paradise 15 minutes to ski hills, sauna jacuzzi1 / 21
    (1)Excellent
    Coldwater
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
    • Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hundreds of acres of walking trails through oak, maple and evergreen trees set on granite hills. Discover multiple lakes with an abundance of wild life. Bring your snowmobiles and explore the local groomed trails part of the Ontario network of snowmobile trails. Skiing is your hobby, experience the...
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    Location Information
    Coldwater, Ontario L0K 1E0
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Clean Picturesque Boater Paradise1 / 23
    (3)Very good
    Severn
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Patio
    • Balcony
    • Cable/satellite TV
    • Internet Access
    • Grill
    • Waterfront
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 October 2017
    Nice location. If you are allergic to mold and mildew please stay away.Messy and cluttered. There is a lot of emphasis on renters cleaning up when they leave but appears that...
    Reviewed 13 June 2017
    The view of the river was amazing, the cottage was really cute and had everything we needed. Lone having access to the canoë and rowboat! will book again and recommend to...
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    About this property
    Boating paradise only 1.5 hours from Toronto! Waterfront, on the Severn River (part of the Trent-Severn System) just minutes from Sparrow Lake. APPROX. Lat Long.: 44.790501,-79.392239. Two screened porches (front and rear) plus an outside deck overlooking the river and lawns. Lovely cottage on...
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    Severn, Ontario P0E1N0
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Horseshoe Valley Farm1 / 34
    (2)Excellent
    Horseshoe Valley
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Parking
    • Balcony
    • Central Heating
    • Patio
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 October 2017
    Sheryl was the perfect host. The house was exactly as described. We had a fresh baked apple pie waiting for us when we arrived. Thank you for everything.
    Reviewed 26 December 2016
    This farm house is so amazing! - we had a great winter view through the windows. the living room was so cozy and the TV was great too because we were able to choose from lots of...
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    About this property
    A private, rustic farmhouse on a working farm, where your group or family can spend quality time together in this century farmhouse and enjoy the quiet space around. Decorated with country charm and with modern conveniences. There is a significant amount of space for kids to play, plus a campfire...
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    Location Information
    Horseshoe Valley, Ontario L0L 2E0
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Cozy Chalet in Horseshoe Valley1 / 12
    (1)Excellent
    Horseshoe Valley
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • DVD Player
    • Wi-Fi
    • Patio
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 December 2015
    We rented the cottage for a skiing weekend with another family. It was simply great. Well organized, very clean, and they even went a far as to start the fireplace for us and...
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    About this property
    An amazing location for a fun and relaxing getaway! Relax by the fire in this cozy chalet, surrounded by nature in the heart of beautiful Horseshoe Valley. Fully furnished. Sleeps 14 people. Open concept entertaining area, gas fireplace, large deck, outdoor fire pit, master bedroom with en suit and...
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    Horseshoe Valley, Ontario L4M 4Y8
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Horseshoe Valley Fieldview Farm1 / 21
    (3)Excellent
    Horseshoe Valley
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Secure Parking
    • Central Heating
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 February 2017
    Awesome place, plenty of charm and grace. Owners accomodating and very hospitable. We would love to go back for next family ski trip. It is so close to the ski hills and easy to...
    Reviewed 30 August 2016
    We found the Horse Shoe Valley Fieldview Farm in a pleasant location with ample clean space within with good amneties. Everyone in the group, from kids to grandparents had a...
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    About this property
    Get away from the city and spend some time in the country! Welcome to our 5 bedroom house. This beautiful, updated farmhouse has all the modern amenities you would want in a country setting. Your family or group can spend quality time together in this spacious, private home located on a...
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    Location Information
    Horseshoe Valley, Ontario L0K 1E0
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 12
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    Country Charm - 21 / 13
    (3)Excellent
    Severn Bridge
    3 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
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    • Cable/satellite TV
    • Secure Parking
    • Wi-Fi
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Host Kay Clark has a brilliant renovated farmhouse on a beautiful and peaceful property in Muskoka. I rented from April 2017 - June 2017 while I was working nearby. Some of...
    Reviewed 12 February 2018
    The host was very sweet! She had tons of great suggestions for things to do in the area. Older house with a beautiful large property. Large entrance area to put snowy boots...
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    About this property
    This century old red brick home has 5 bedrooms. Very quiet home is nestled in the woods. Lots of birds and wild life right in the yard. Our gardens make this place a paradise. Home is where the heart is. Please enjoy your stay with us for it is the most important reason why I do open my home, and...
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    Severn Bridge, Ontario P0E 1N0
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 3
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    Severn Bridge
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ‘View Of The Lake’ The ‘View Of The Lake’ cottage is part of the Grandview Lakeside Community Club, a cottage community nestled on Grandview Point at the site of the former Grandview Lodge Resort on Sparrow Lake in the popular Muskoka tourist region. This 2 storey, 1500 sq. ft, 2 bedroom, 1...
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    Severn Bridge, Ontario P0E 1N0
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Sebright
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Internet Access
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautiful waterfront cottage with spectacular lake views. Just a 1 1/2 hours drive from Toronto and less than 30 minutes from downtown Orillia, this updated all-season vacation home offers panoramic water views and the serenity of cottage life. Situated on the shores of Lake Dalrymple, this 1350...
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    Sebright, Ontario L3V 6H5
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Severn
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand new house fetures a basement brand new apartment. Can accommodate min 4 people and more. Breakfast can be served as well. Close by : lakes, fun summer/winter activities. All season long. Has a kitchenette as well. Barbecue available upon request. More rooms are also available through out the...
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    Severn, Ontario L3V0V8
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Severn Bridge
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This comfortable and fully equipped 3 season cottage is a great vacation choice, located in a Muskoka family resort community on the beautiful Trent-Severn Waterway just a 90 minute drive from Toronto. You can enjoy all the recreational amenities of a waterfront resort. If you are a boater, the...
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    Severn Bridge, Ontario L0K 2B0
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Horseshoe Valley
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Housekeeping Included
    • Wi-Fi
    • Balcony
    • Patio
    • Sauna
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fork in the Trail is a three-room Bed & Breakfast, not a rental cottage. We are situated on 100 acres of rolling hardwood bush with trails throughout for hiking, biking, snow shoeing and cross country skiing. A variety of paved road cycling routes are directly accessible. Minutes from Horseshoe...
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    Location Information
    Horseshoe Valley, Ontario L0L 2E0
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Brechin
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    it's very beautiful house beside Lake Simcoe, located in lagoon city, 150 km north of Toronto, and 150 km to the international airport, we have the private duck to park the boat up to 60' longer, the house are complete new decoration with new furnishing, the modern home designs and nature...
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    Brechin, Ontario L0K 1B0
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Severn Bridge
    2 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
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    • Housekeeping Included
    • Private Garden
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Country Charm. We have 4 rooms in the main country home available, but we are expanding our cabin rentals in the surrounding woods. Renting the 6 person cabin comes with a BBQ. The cabin does not have a refrigerator and you need a sleeping bag and pillow and flash lights. Washroom facilitry is...
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    Severn Bridge, Ontario P0E 1N0
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 3
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    Brechin
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Patio
    • Central Heating
    • Cable/satellite TV
    • DVD Player
    • Waterfront
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property is just off Lake Simcoe with 100' of shorewall with southern exposure for full sun all day and is suitable for large boat dockage including shore power, phone and fresh water located at the mouth of Lagoon City on Lake Simcoe. This spacious houses offers the top two levels for you...
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    Brechin, Ontario L0K 1B0
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Severn Bridge
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Waterfront
    • Internet Access
    • Washer
    • Parking
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully winterized with hardwood and tile flooring, lighting, stone patio, limestone steps & flagstone walkway leading to timber frame entrance, new decks & a floating dock to accommodate a 26 foot boat. About 3,000 sq.ft. of living space with 4 spacious bedrooms & 3 baths with lots of room for...
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    Severn Bridge, Ontario P0E 1N0
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Cumberland Beach
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Central Heating
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    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Modern Century Cottage was in the same family for more than 100 years. Expertly renovated & decorated by the design build team at Prime 2015, it retains its original charm and character. This traditional cottage puts you right in the heart of cottage country with spectacular swimming, hiking, cross...
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    Cumberland Beach, Ontario L3V 6H6
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Cumberland Beach
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    “THE COTTAGE” Only 90 minutes from downtown Toronto and virtually on the water - this cottage is just a short walk across the road to a private park and sandy beach on the shore of beautiful Lake Couchiching. You can see the water from your front deck. Lake Couchiching is part of the historic...
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    Cumberland Beach, Ontario L3V 6H3
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    Family Cottage for rent1 / 37
    (1)Very good
    Brechin
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Wi-Fi
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    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Exclusive Lagoon City, Brechin, On Waterfront cottage facing 2 water canals, access to Lake Simcoe by water or land, 2 blocks from Sandy private beach This is a year round cottage You’ll love our Year around Cottage because of the ambiance, big outdoor space and house comfort. Drinkable tap...
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    Location Information
    Brechin, Ontario L0K 1B0
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Horseshoe Valley
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Grill
    • Sauna
    • Skiing: Property Is In A Ski Resort
    • Balcony
    • Hot Tub
    • Housekeeping Included
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Horseshoe Valley, just one hour north of Toronto, a four-season natural playground with rolling hills and forested trails. Whether you want to ski meticulously groomed trails through snow-laden forests of pine, tee off at one of eighteen area golf courses, hike or mountain bike one of...
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    Location Information
    Horseshoe Valley, Ontario L0L 2L0
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Severn Bridge
    4 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Country Charm. We have 4 rooms in the main country home available, but we are expanding our cabin rentals in the surrounding woods. Renting the 6 person cabin comes with a BBQ. The cabin does not have a refrigerator and you need a sleeping bag and pillow and flash lights. Washroom facilitry is...
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    Severn Bridge, Ontario P0E 1N0
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 2
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    Severn Bridge
    4 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Smoking allowed
    About this property
    Country charm. We have1 rooms in the main country home available, there are a total of 4 rooms. We are expanding our cabin rentals in the surrounding woods. Our century old home has lots of charm and of course a very friendly atmosphere. Renting the cabin comes with a BBQ. The cabin does not have...
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    Location Information
    Severn Bridge, Ontario P0E 1N0
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 3
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    Horseshoe Valley
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Sauna
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Shared Indoor Pool
    • Housekeeping Included
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I'm offering March Break (March 10 -17checkout) at our time-share at Carriage Hills Resort, set in the beautiful Horseshoe Valley premier ski area, just west of Orillia. Spacious and private, with fully equipped kitchen, and access to a great pool, sauna, hot tubs and other amenities; special ski...
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    Location Information
    Horseshoe Valley, Ontario L0L 2L0
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Brechin
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on a private Lane in Cottage Land - Our place is an upper Level - 900 sq ft. Full gourmet kitchen with dishwasher - Dishes- Spices and Condiments. 2 Smart TV's with satellite and internet - 2 bedroom - Upgraded Spa like Beds, Pillows and Linens. The owners reside on the lower level to...
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    Location Information
    Brechin, Ontario L0K 1W0
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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