The 19 Best Holiday Rentals in Durham Region

based on 296 Holiday Rental Reviews on Booking.com

• Adorable Quiet Open Concept Private Studio Suite

  Ranked 1 out of 39 in the region, as well as being 1 of 10 for holiday rentals in Ajax.

  Last review posted: 8 days ago

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  • “The place is perfect!”
  • “This place is great! Matches the description, clean, open, quiet neighbourhood, comfortable, owners are polite and respe”
  • “Clean and cozy!”
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• Family Friendly - Cozy - HOT TUB - Near UOIT

  Ranked 2 out of 39 in the region, as well as being 2 of 11 for holiday rentals in Oshawa.

  Last review posted: 92 days ago

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  • “Wonderful!”
  • “Very clean, host was very kind.”
  • “A home away from home!”
  • See more reviews of Family Friendly - Cozy - HOT TUB - Near UOIT

  
• Guest Suite in Whitby

  Ranked 3 out of 39 in the region, as well as being 1 of 6 for holiday rentals in Whitby.

  Last review posted: 44 days ago

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  • “The whole unit was amazing and I felt too comfy staying...”
  • “House was super clean and the host provided snacks :)”
  • “Great host ,and very considerate and kind host”
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• Vacation Suite in Pickering

  Ranked 4 out of 39 in the region, as well as being 3 of 12 for holiday rentals in Pickering.

  Last review posted: 120 days ago

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  • “Wonderful place”
  • “Great locality, fine people, really clean and modern...”
  • “Beautiful home, host was friendly and quick to respond.”
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• Modern bright cozy 3bed 3bath Vacation house in Ajax, greater Toronto area GTA, ON, Canada

  Ranked 5 out of 39 in the region, as well as being 4 of 10 for holiday rentals in Ajax.

  Last review posted: 30 days ago

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  • “Perfect house for a family!”
  • “Excellent stay”
  • “It was so good and peaceful place to stay over.”
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• Adorable Private Suite in Ajax, unique 2 story

  Ranked 6 out of 39 in the region, as well as being 6 of 10 for holiday rentals in Ajax.

  Last review posted: 8 days ago

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  • “We would always stay at this place again.”
  • “It was a pleasant experience and would recommend it to anyone.”
  • “great location, great host”
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• Beautiful Walk out Basement Apartment in Pickering near Beach

  Ranked 7 out of 39 in the region, as well as being 4 of 12 for holiday rentals in Pickering.

  Last review posted: 15 days ago

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  • “My family of four from Baltimore MD, had a great time visiting Canada, and had a good stay.”
  • “our stay was amazing”
  • “Would highly recommend for anyone that needs a comfortable home”
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• Furnished Family Home near Toronto - Great Location Game Room - Backyard - Parking & Self Checkin

  Ranked 8 out of 39 in the region, as well as being 6 of 12 for holiday rentals in Pickering.

  Last review posted: 41 days ago

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  • “Wonderful - exceeded all expectations!”
  • “Will book again next time definitely”
  • “Nice and well located house”
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• Cosy 3-Bedroom Home in Quiet Cul-de-Sac.

  Ranked 9 out of 39 in the region, as well as being 7 of 12 for holiday rentals in Pickering.

  Last review posted: 104 days ago

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  • “Would definitely stay there again .”
  • “Best place we booked ever”
  • “Perfect place to stay for our vacation,”
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• Comfy 2 Bedroom Near The Beach!

  Ranked 10 out of 39 in the region, as well as being 8 of 12 for holiday rentals in Pickering.

  Last review posted: 25 days ago

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  • “Terrible!!”
  • “Size, secured, location was important for us”
  • “cleanliness, comfortable, most necessities were there.”
  • See more reviews of Comfy 2 Bedroom Near The Beach!

  
• The Oasis

  Ranked 11 out of 39 in the region, as well as being 5 of 6 for holiday rentals in Bowmanville.

  Last review posted: 24 days ago

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  • “Everything almost felt like home”
  • “Accident it absolutely absolutely amazing”
  • “Services provided were exceptional, professional and affordable for such beautiful and comfortable property. It is indee”
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• Entire 4 bed room detached residential home

  Ranked 12 out of 39 in the region, as well as being 7 of 10 for holiday rentals in Ajax.

  Last review posted: 56 days ago

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  • “enjoyed! would stay again for sure!”
  • “I enjoyed and felt relaxed in our stay.”
  • See more reviews of Entire 4 bed room detached residential home

  
• Room in Oshawa, 24/7 Security, Free Parking

  Ranked 13 out of 39 in the region, as well as being 5 of 11 for holiday rentals in Oshawa.

  Last review posted: 6 days ago

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  • “A very nice room friendly hosts”
  • “Good”
  • “Other than lack of kitchen access to cooking, property was ok”
  • See more reviews of Room in Oshawa, 24/7 Security, Free Parking

  
• Prestige Accommodation Self-contained 2 Bedrooms Suite

  Ranked 14 out of 39 in the region, as well as being 8 of 10 for holiday rentals in Ajax.

  Last review posted: 2 days ago

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  • “The property was clean, beds were very comfortable, and easy...”
  • “very satisfied”
  • “Ok”
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• Spacious and bright unit with natural light.

  Ranked 15 out of 39 in the region, as well as being 9 of 12 for holiday rentals in Pickering.

  Last review posted: 50 days ago

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• Finished 2 BR Apartment in an Upscale Area of Ajax

  Ranked 16 out of 39 in the region, as well as being 9 of 10 for holiday rentals in Ajax.

  Last review posted: 52 days ago

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  • “It was a beautiful place the tenets were amazing would definitely stay again!!”
  • “This place had everything we needed and exactly as described.”
  • “Overall worth the price for sure.”
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• Stylish Retreat in North Oshawa

  Ranked 17 out of 39 in the region, as well as being 7 of 11 for holiday rentals in Oshawa.

  Last review posted: 3 days ago

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  • “friendly host,good location,very clean.”
  • “Would go back again and would recommend it to anyone”
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• Large Separate Entrance Basement Unit 2Beds 1Washroom Sleeps 4-6

  Ranked 18 out of 39 in the region, as well as being 10 of 12 for holiday rentals in Pickering.

  Last review posted: 63 days ago

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  • “The neighborhood is upscale, and parking is right out front,...”
  • “The was cosy and exactly what we needed”
  • “Great value. We would stay here again.”
  • See more reviews of Large Separate Entrance Basement Unit 2Beds 1Washroom Sleeps 4-6

  
• 1 bedroom apartment w/Wifi and private entrance

  Ranked 19 out of 39 in the region, as well as being 10 of 10 for holiday rentals in Ajax.

  Last review posted: 12 days ago

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  • “Perfect stay for a couple”
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