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Cumberland Beach Vacation Rentals

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    Don't let other travelers get your favorite Cumberland Beach area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 22 Rentals in Cumberland Beach
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    The Cottage (#880)1 / 20
    (2)Average
    Cumberland Beach
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    The following rentals are within 10 miles of Cumberland Beach.
    Country Charm - 21 / 13
    (3)Excellent
    Severn Bridge
    3 Bedrooms, 1 Bathroom, Sleeps 3 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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    Family Cottage Escape on Lake Couchiching1 / 12
    (1)Excellent
    Orillia
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Grill
    • Parking
    • Terrace
    • Private Yard
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 16, 2015
    Beautiful spot on Lake Couchiching! Very clean!! With all amenities, Full kitchen and BBQ, 6 beds. Facing west to enjoy the afternoon sun and beautiful sunsets. Decent...
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    About this property
    Our four bedroom two bathroom cottage would be great for a family reunion or a shared vacation with another family. With six beds the cottage comfortably sleeps eight people. The outside prperty is ideal for summer swimming and boating. There is a large dock that extends out from the shore about...
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    Location Information
    Orillia, Ontario LOK 1B0
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Severn Bridge
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Private Yard
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Light breakfast comes with his sweet cabin in the morning. Insulated with a small deck on the front and side. Washroom facilities are in the main house when you walk into the Muskoka room the cabin is 10 X 12 and features French doors and 2 other windows Cabin is new to our accommodations Has...
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    Severn Bridge, Ontario P0E 1N0
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just an hour and a half drive from Toronto, the Redwood Retreat is a well maintained and welcoming waterfront cottage situated on the north shores of Lake Simcoe with easy access to downtown Orillia and Casino Rama. Whether it is lazy days in the sun while taking occasional dips in the lake,...
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    Orillia, Ontario L3V 6H7
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Severn Bridge
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Yard
    • Wi-Fi
    • Housekeeping Included
    • Cable/satellite TV
    • Secure Parking
    Suitability
    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 2
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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 October 11, 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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    Location Information
    Orillia, Ontario L3V 6H2
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Severn Bridge
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • 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
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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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 October 5, 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 June 13, 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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    Location Information
    Severn, Ontario P0E1N0
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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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 July 18, 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 August 28, 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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    Location Information
    Orillia, Ontario L0K 1W0
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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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    Location Information
    Orillia, Ontario L3V 0K2
    Rental Home - 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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    Location Information
    Orillia, Ontario L3V 0K2
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    Severn Bridge
    4 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Parking
    • Private Yard
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Country charm. We have 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 a...
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    Location Information
    Severn Bridge, Ontario P0E 1N0
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 3
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    Severn Bridge
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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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    Location Information
    Severn Bridge, Ontario P0E 1N0
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Severn Bridge
    4 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Wi-Fi
    • Air Conditioning
    • Private Yard
    • Parking
    • Cable/satellite TV
    Suitability
    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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    Location Information
    Severn Bridge, Ontario P0E 1N0
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 2
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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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    Location Information
    Severn, Ontario L3V0V8
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Severn
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Parking
    • Private Yard
    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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    Location Information
    Severn, Ontario L0K 1E0
    Cabin - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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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
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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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 Yard
    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Orillia
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Private Yard
    • 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
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    Orillia
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • 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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Exchange rate: 1 Canadian Dollars = 0.77 U.S. Dollars
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