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Holiday Rentals in Orillia

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    ₹ 18,812 Average
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    ₹ 0₹ 74,000+
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    Travellers to Orillia are booking June dates now. Secure your holiday home today, and have the perfect trip.
    All 19 Rentals in Orillia
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    Redwood Retreat cottage (#828)1 / 22
    (1)Average
    Orillia
    3 Bedrooms, 2 Bathrooms, Sleeps 8 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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    Leaning Tree Cottage1 / 34
    (3)Very good
    Orillia
    3 Bedrooms, 1 Bathroom, Sleeps 10 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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    Amenities & Details
    • Central Heating
    • Waterfront
    • Wi-Fi
    • Balcony
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 October 2016
    Had a great time at this cottage. It is located very close to shopping so is convenient. Great waterfront and lake. Excellent for water sports. A dock is present which allowed...
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    About this property
    Whispering Pines Cottage is rated as a 5* VACATION PROPERTY on Trip Advisor and is one of Flip Key's most popular locations. Owners have just had a change of plans and their beautiful cottage is available from June 1st onwards. Please note that there are no pets allowed at this property and...
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    Orillia, Ontario L3V 6H2
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Orillia
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Waterfront
    • Patio
    • Air Conditioning
    • Skiing: Property Is In A Ski Resort
    • Housekeeping Included
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    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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    Amenities & Details
    • 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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    Orillia, Ontario L3V 0K2
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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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
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 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 29 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
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Terrace
    • Waterfront
    • Grill
    • Washer
    • Balcony
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    You are guaranteed to fall in love with our home! This newly built, all season cottage on a lake is only 60 min away from GTA! This beautiful, over 5,500 sq. feet home sits on an acre of land and includes 6 specious bedrooms, 5 baths, fully loaded open concept kitchen, large dining table and...
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    Orillia, Ontario L3V 6H1
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    Orillia
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and unwind at newly built, all season cottage with a lake front view! Just a 90 min drive from Toronto we’ve got everything you need for relaxing and re-energizing getaway! This beautiful, over 5,500 sq. feet home sits on an acre of land and includes 6 specious bedrooms, 5 baths, fully loaded...
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    Location Information
    Orillia, Ontario L3V 6H1
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    Orillia
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • 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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    Location Information
    Orillia, Ontario L3V 0E2
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Orillia
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Washer
    • Central Heating
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My home is a beautiful big place with lots of character. It has high vaulted ceilings with skylights. My home backs into the forest which is for me the best part as you can enjoy your coffee in the morning on the covered porch rain or shine. You can see squirrels, birds and sometime even the...
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    Location Information
    Orillia, Ontario L3V 7Y4
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    The following rentals are within 15 kilometres of Orillia.
    The Cottage (#880)1 / 20
    (2)Average
    Cumberland Beach
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Washer
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 August 2018
    We had not rented a cottage for many years. This cottage was perfect for our now adult family. My 93 year old mother also came with us for 3 days. The cottage was a perfect size...
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    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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    Clean Picturesque Boater Paradise1 / 23
    (3)Very good
    Severn
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • 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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    Oro-Medonte
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waiting for you beyond the gates of Ravens Ridge is a nature based sanctuary. A unique spot to Refresh, Recharge and Reset yourself. It is a perfect base for exploring the four seasons of Simcoe County and the region of Muskoka. Catherine Jenereaux is your host. As guardian of the property she has...
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    Oro-Medonte, Ontario L0L 1T0
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Oro-Medonte
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Central Heating
    • Patio
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waiting for you beyond the gates of Ravens Ridge is a nature based sanctuary. A unique spot to Refresh, Recharge and Reset yourself. It is a perfect base for exploring the four seasons of Simcoe County and the region of Muskoka. Catherine Jenereaux is your host. As guardian of the property she has...
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    Location Information
    Oro-Medonte, Ontario L0L 1T0
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Severn
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Incredible Scandinavian , fully-scribed, white pine log home. Originally constructed by the students of the Pat Wolf Log Building School, Coldwater Cabin is 17th century European chinkless log construction at its finest. Two stories with an additional finished loft. Recently updated kitchen...
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    Severn, Ontario L0K 1E0
    Cabin Holiday Rental - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Oro-Medonte
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Central Heating
    • Sauna
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waiting for you beyond the gates of Ravens Ridge is a nature based sanctuary. A unique spot to Refresh, Recharge and Reset yourself. It is a perfect base for exploring the four seasons of Simcoe County and the region of Muskoka. Catherine Jenereaux is your host. As guardian of the property she has...
    View all property information
    Location Information
    Oro-Medonte, Ontario L0L 1T0
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Severn
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Oro-Medonte
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Housekeeping Included
    • Sauna
    • Shared Indoor Pool
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Oro-Medonte, Ontario L0L 2L0
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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