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Holiday Apartments in Cumberland Beach

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    Don't let other travellers get your favourite Cumberland Beach area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 22 Rentals in Cumberland Beach
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    Cumberland Beach
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    The following rentals are within 15 kilometres of Cumberland Beach.
    Clean Picturesque Boater Paradise1 / 23
    (3)Very good
    Severn
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Orillia
    7 Bedrooms, 5 Bathrooms, Sleeps 16 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 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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    L0K 1W0, Orillia, Ontario
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Leaning Tree Cottage1 / 34
    (3)Very good
    Orillia
    3 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    Amenities & Details
    • Waterfront
    • Grill
    • Central Heating
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Cottage and property were great. View was lovely and neighbours were friendly.Dominic was quick to respond to emails with questions we had prior to our visit.The only...
    Reviewed 19 October 2017
    Had a wonderful stay. Dock and deck were terrific for fishing and eating outside...we laughed a lot, played together and slept well. The cottage was equipped with all the...
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    About this property
    Leaning Tree Cottage is located directly on the water with private dock and Sandy beach on Crystal clear Lake Couchiching. We are on the West side of the Lake, just north of the Weber's Hamburger restaurant on Highway 11. The water is waist deep for 200+ feet out and very child friendly....
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    L3V6H7, Orillia, Ontario
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 10
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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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    Amenities & Details
    • Wi-Fi
    • Grill
    • Parking
    • Terrace
    • Private Garden
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 September 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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    LOK 1B0, Orillia, Ontario
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Country Charm - 21 / 13
    (3)Excellent
    Severn Bridge
    3 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Private Garden
    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 March 2018
    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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    P0E 1N0, Severn Bridge, Ontario
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 3
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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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    L3V 6H2, Orillia, Ontario
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Severn Bridge
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Garden
    • 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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    P0E 1N0, Severn Bridge, Ontario
    Holiday Rental House - 1 Bedroom, 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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    L3V0V8, Severn, Ontario
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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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    L3V 0K2, Orillia, Ontario
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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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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    P0E 1N0, Severn Bridge, Ontario
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Severn Bridge
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Private Garden
    • 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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    P0E 1N0, Severn Bridge, Ontario
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 2
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    Severn
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • 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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    L0K 1E0, Severn, Ontario
    Cabin Holiday Rental - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    L3V 0K2, Orillia, Ontario
    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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    L3V 0E2, Orillia, Ontario
    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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    • 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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    L3V 7Y4, Orillia, Ontario
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Severn Bridge
    4 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Parking
    • Private Garden
    • 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
    P0E 1N0, Severn Bridge, Ontario
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 3
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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 Garden
    • 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
    P0E 1N0, Severn Bridge, Ontario
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 2
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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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    P0E 1N0, Severn Bridge, Ontario
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Orillia
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • 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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    L3V 6H1, Orillia, Ontario
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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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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    • 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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    L3V 6H7, Orillia, Ontario
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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