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Collingwood Holiday Rentals with Pools

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    Travellers to Collingwood are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    31 Matching Rentals in the Collingwood AreaView all 102 rentals
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    Spacious 1 Bedroom Condo that Sleeps 61 / 7
    (2)Very good
    Collingwood
    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Modern Vacation Condo Collingwood min from Lake, Blue Mountain and Spa1 / 22
    (4)Excellent
    Collingwood
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Collingwood
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    MARCH BREAK SPECIAL! Spacious 14 person home- steps from the village *HOT-TUB*1 / 94
    (4)Very good
    Collingwood
    6 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Mountain Views
    • Washer
    • Hot Tub
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 September 2019
    A great space for our group of 14. So much to do with the pool table, fire pit, hot tub and tennis court (pool closed before we arrived). Lots of space, many amenities and clean...
    Reviewed 23 July 2019
    We stayed at the property this past weekend . We had a large group and this house was just what we needed. The kitchen is fully stocked . Some items to bring of your own...
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    About this property
    Right at the base of Blue Mountain and walking distance to the Village, this 4,000 square foot chalet offers 6-bedrooms, 3 bathrooms and 2 large family rooms as well as an enormous eat-in kitchen with stunning views of Blue Mountain. There is plenty of space for large family gatherings. Sleeps 14...
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    Collingwood, Ontario L9Y 0M7
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 14
    Collingwood
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Sauna
    • Washer
    • Hot Tub
    • DVD Player
    • Mountain Views
    • Air Conditioning
    • Shared Indoor Pool
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    .•:*¨¨*:•. Georgian Manor Resort in Collingwood, Ontario Canada .•:*¨¨*:•. AVAILABLE JULY 18 - 25, 2015 > only an 8 min drive to the Elvis Presley festival in downtown Collingwood, July 23-26, 2015 > 1 Bedroom Suite with 1 Sofa Bed, Sleeps up to 4 People ( $48.85 per night, per person for 4...
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    Collingwood, Ontario L9Y 5G4
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Collingwood
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Air Conditioning
    • Porch
    • Mountain Views
    • DVD Player
    • Hot Tub
    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Close to Blue Mountains and the Village, this condominium is perfect for the couple or family looking to retreat to Collingwood for the winter season. Close to downtown Collingwood for arts, theatre, shopping and many fabulous, quaint restaurants. For those looking for a cozy, warm and...
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    Collingwood, Ontario L97 5C5
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Quiet Getaway - Lots of Winter Attractions - Perfect for a Couple or Family!1 / 27
    (9)Excellent
    Collingwood
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Collingwood, Ontario L9Y 3Z1
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Family Friendly Condo with Year Round Swimming Pool- Minutes to Blue Mountain!1 / 29
    (2)Excellent
    Collingwood
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
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    • Internet Access
    • Parking
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Collingwood, Ontario L9Y 0X4
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Seasonal Family Condo Rental near Blue Mountain1 / 18
    (3)Excellent
    Collingwood
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Central Heating
    • Washer
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Sauna
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Collingwood, Ontario L9Y 5C7
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Collingwood
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Wi-Fi
    • Shared Indoor Pool
    • Cable/satellite TV
    • Balcony
    • Air Conditioning
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is our timeshare resort week, but we cannot go this year. All the paperwork for your stay at the resort will be done properly with Georgian Manor. Available for seven nights Dec 23-30, 2017. Luxury unit in Georgian Manor Resort in Collingwood, 10 min. drive to Blue Mountain skiing. Master...
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    Collingwood, Ontario L9Y 5G4
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lovely Vacation Condo, Collingwood minutes to Lake & Blue Mountain Village & Spa1 / 17
    (2)Excellent
    Collingwood
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Skiing: Property Is In A Ski Resort
    • Balcony
    • Wi-Fi
    • DVD Player
    • Washer
    • Children's Pool
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 January 2019
    We thoroughly enjoyed ourselves at this exceptionally clean and well equipped condo. It was so close to many things to do in the area. It was actually our third time at this...
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    About this property
    Condominium is located in Collingwood in the Heart of Cranberry Resort - Next to Living Stone Golf Resort, Hwy 26/Keith Ave. Feel at Home in this Lovely Smoke-Free Fully Furnished and Equipped 1 Bdrm, 2 Beds and 1 Bath Condo Suite offering comfortable living in Cottage-like Settings. HD Smart 3D...
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    Collingwood, Ontario L9Y 5B4
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Collingwood
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Collingwood, Ontario, this resort is nearby the Blue Mountains and the Georgian Bay. This 750-acre resort features a full-service marina and spa along with an 18-hole golf course. At the Cranberry Golf Resort, guest rooms include free Wi-Fi, a coffee maker and cable TV. Select condos...
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    Collingwood, Ontario L9Y 4T9
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    The following rentals are within 15 kilometres of Collingwood.
    Luxury Studio Getaway at Blue Mountains!1 / 30
    (4)Excellent
    Craigleith
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 July 2019
    Great location to blue mountain and not too far from wasaga beach.Nice Ikea kitchen with everything you might need, only wish the deck and sliding door (sticks) were more...
    Reviewed 10 April 2019
    I just love this unit!! I have stayed here a couple of times, and wouldn’t hesitate to recommend it to anyone. It’s a perfect little getaway with everything you need all in one...
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    About this property
    Welcome to our little slice of luxury in Blue Mountains. We have designed our cozy studio to resemble a 'home away from home' for our guests. As you enter into the main floor unit, you will encounter a clean, modern design with rustic accents that feels warm and welcoming. The main living area is...
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    Craigleith, Blue Mountains L9Y 0N6
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Craigleith
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A luxurious, stunning 3 bedroom (can sleep up to 8) french style oak and cedar chalet, 5 minute drive to Blue mountain (intrawest). Amenities are;pool ,10 pers hot-tub(PRIVATE), surround sound system throughout, 55 inch flat screen TVS, fully equipped kitchen with stainless steel appliances,gas...
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    Craigleith, Blue Mountains L9Y 0S8
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Claire Glen1 / 24
    (2)Excellent
    Craigleith
    8 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
    • Secure Parking
    • Wi-Fi
    • Air Conditioning
    • Private Indoor Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 September 2018
    Our stay at the chalet (116 Claire Glen) was great! I would definitely come back here. Clean home with a great pool & Jacuzzi. Not only were we happy with the...
    Reviewed 6 March 2018
    Our group of 14 stayed there this past weekend. We went for a ski trip but most just stayed in the cottage. It was comfortable, clean and fun. You are about 2 minutes drive from...
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    About this property
    Located only a short walk away to Blue Mountain Resorts and village, Claire Glen is the ultimate chalet for privacy in a tree filled and relaxing community. Claire Glen chalet features a full indoor pool open for use all year round. Sliding glass doors provide sunlight and access to an outdoor hot...
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    Craigleith, Blue Mountains L9Y 0P1
    Holiday Rental House - 8 Bedrooms, 4 Bathrooms, Sleeps 16
    Craigleith
    6 Bedrooms, 2 Bathrooms, Sleeps 13 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Attracting visitors year-round, 128 Birch View Trail offers views of Blue Mountain from inside the chalet to the upper patio. The chalet is a private rental at Blue Mountain, yet it’s only a 15-minute walk to the base of Blue Mountain Ski Resort. The Blue Mountains is located only an hour and a...
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    Craigleith, Blue Mountains L9Y 0M2
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 13
    Fabulous 2 Bdrm, 2-Level Condo on Blue Mountain1 / 22
    (8)Very good
    Craigleith
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Grill
    • Washer
    • Mountain Views
    • DVD Player
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 November 2018
    This condo was clean and cozy. The netflex was handy too. I would suggest leaving a shovel for guests to clean off the stairs though. Also, it took quite a while to warm the...
    Reviewed 21 June 2018
    The condo was next to a stream coming off the mountain that was very restful. The condo was clean and well appointed and we enjoyed our stay. Thanks for asking. Susan USA
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    About this property
    This beautiful two-bedroom, two-level condo is located in scenic Collingwood/Blue Mountains, Ontario. Nestled at the base of Blue Mountain with ski-in, ski-out access(snow conditions permitting) to Blue Mountain's North Chair(expert terrain),this tranquil and light-filled vacation home features...
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    Craigleith, Blue Mountains L9Y 0P5
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Craigleith
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Wi-Fi
    • Children's Pool
    • Air Conditioning
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Snowbridge 123 Whether you’re looking for a convent and spacious home away from home for you and your friends or the perfect and cozy retreat for your next family getaway, you’ll have everything and more at this charming condo at Snowbridge! This retreat features a convenient open concept that...
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    Craigleith, Blue Mountains L9Y 0V1
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Craigleith
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
    • Mountain Views
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rivergrass 224 Rivergrass 224 is the dog-friendly mountain condo you and your friends or family need to truly enjoy an unforgettable Canadian getaway! It’s been tastefully decorated and features everything you may need to take delight in a carefree vacation. Enjoy your morning coffee with views of...
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    Craigleith, Blue Mountains L9Y 0P8
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Craigleith
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
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    • Children's Pool
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Snowbridge 40 Make your dreams of a wonderful and unforgettable ski-cation come true at Snowbridge 40! Boasting a sleek minimalist interior decor, a convenient open concept, and enough space to accommodate up to eight guests, you won’t find a more memorable vacation rental than this one. Take...
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    Craigleith, Blue Mountains L9Y 0V1
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Craigleith
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Children's Pool
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Snowbridge 218 Book this delightful and conveniently located condo to experience year-round fun and excitement! With an open layout that combines the kitchen, living room, and dining room, togetherness shouldn’t be a problem. Treat your guests to homemade meals prepared in the fully-equipped...
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    Craigleith, Blue Mountains L9Y 0V1
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Craigleith
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Balcony
    • Hot Tub
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    • Cable/satellite TV
    • Terrace
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rivergrass 211 Whether you’re looking for the perfect place to host your next family getaway or a great home base to start creating everlasting memories with your group of friends, this condo at the Lodges At Blue Mountain is exactly what you’ve been looking for! This charming retreat sleeps up to...
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    Craigleith, Blue Mountains L9Y 0P8
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Craigleith
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Snowbridge 241 This classic and spacious Canadian getaway is here to provide you with year-round fun and excitement! Featuring high vaulted ceilings, creamy white and subtle brown touches throughout that give this retreat a sleek look, and an open concept that combines the kitchen, living room, and...
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    Craigleith, Blue Mountains L9Y 0V1
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    Craigleith
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sierra Lane 205 Create everlasting memories of your family trip to Ontario at this gorgeous, recently renovated condo at Sierra Lane! Featuring high ceilings, creamy white walls, and comfortable and elegant furnishings throughout, Sierra Lane 205 is every family’s dream come true. Gather and unwind...
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    Craigleith, Blue Mountains L9Y 0P8
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    Craigleith
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    • Grill
    • Wi-Fi
    • Washer
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sierra Lane 214 With an unbeatable location near skiing, mountains, and downtown Blue Mountain Village, a spacious and well-furnished living area, plenty of space for the entire group to spread out comfortably, and access to a shared pool, there’s no better place to stay than Sierra Lane 214 at the...
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    Craigleith, Blue Mountains L9Y 0P8
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    Craigleith
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Cable/satellite TV
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Snowbridge 208 The moment you enter Snowbridge 208, you wouldn’t want to leave! You’ll be welcomed by a sleek, yet homey interior decor featuring white creamy walls adorned with tasteful decorations and an open concept combining the kitchen, living room, and dining room together. Let your guests...
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    Craigleith, Blue Mountains L9Y 0V1
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Craigleith
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Mountain Views
    • Shared Outdoor Pool (Unheated)
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sierra Lane 212 Enjoy the peace and quiet you’ve been looking for at this spacious condo at Sierra Lane! This lovely getaway offers a prime location and enough space for the entire group to spread out and unwind in style. Prepare some delicious snacks and beverages in the fully-equipped kitchen,...
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    Craigleith, Blue Mountains L9Y 0P8
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 10
    Craigleith
    Studio, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Condo 916 at North Creek Resort Lovingly renovated and ideally located in the North Creek Resort complex, this open-concept loft offers unbeatable access to the ski slopes of Blue Mountain Resort, nearby golf courses, and beautiful beaches on the shores of South Georgian Bay. Enjoy such thoughtful...
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    Craigleith, Blue Mountains L9Y 0B5
    Condo/Apartment - 2 Bathrooms, Sleeps 6
    Craigleith
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Children's Pool
    • Mountain Views
    • DVD Player
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    • Skiing: Property Is In A Ski Resort
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This renovated two bedroom and two bath townhouse is located in the heart of the beautiful Historic Snowbridge Community of Blue Mountain and is situated directly on a Golf Course. This 2 Storey loft has beautiful views but you simply cannot beat the incredible amenities. It sleeps 5, contains...
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    Craigleith, Blue Mountains L9Y 0V1
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Stayner
    5 Bedrooms, 3 Bathrooms, Sleeps 35 Quick View
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    • Wi-Fi
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    • Private Garden
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Clearview Manor! A spacious countryside Estate on 85 acres. Conveniently located near Wasaga Beach and a short distance to Collingwood. The property features lavish green fields, a seasonal sparkling swimming pool, a hot tub, a natural pond with various fish, wood burning fire pit,...
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    Stayner, Clearview Township L0M 1S0
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 35
    Wasaga Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Washer
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    • Shared Indoor Pool
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for the perfect stay during this 2019/2020 Winter Season? Looking somewhere to stay during your business trip or spend the holidays? This beautiful seasonal rental chalet with interior log cabin décor boasts vaulted ceilings with open living spaces and cozy private bedrooms. It also comes...
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    Location Information
    Wasaga Beach, Ontario L9Z 1X7
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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