Top Private Holiday Homes in Durham Region in 2026

Durham Region Private Holiday Homes
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A historic building with a green roof, surrounded by well-maintained gardens and a stone fence.

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Our top choices for Durham Region holiday homes

A living room with a sofa, a coffee table, and a TV mounted on the wall.

A modern kitchen with a built-in oven and a marble-top dining table with chairs.

A bedroom with a bed, a door with a sheer curtain, and a light switch on the wall.

A modern kitchen with white cabinets, a marble countertop, a stove, a microwave, and a sink.

1. Oshawa Suite Open Kitchen Living Space

Oshawa Suite Open Kitchen Living Space

2.0 star property

Donevan

The price is RM232

RM232

RM276 total

includes taxes & fees

15 Oct - 16 Oct

Oshawa Suite Open Kitchen Living Space

2. Cozy Whitby Retreat - 2 Bedroom Private House

Cozy Whitby Retreat - 2 Bedroom Private House

2.0 star property

Whitby

Cozy Whitby Retreat - 2 Bedroom Private House

A spacious living area with a fireplace, a dining table, and a large window.

A hotel room with a large bed, two bedside lamps, a chair, a small table, and a view of the outside through the windows.

A two-story house with a brick facade, a gabled roof, and a covered porch.

A spacious living area with a dining table, a sofa, and a staircase.

3. King Bed, Home Gym, 4 Tvs, Near Recreational Parks, Tennis Court, Shoping Center

King Bed, Home Gym, 4 Tvs, Near Recreational Parks, Tennis Court, Shoping Center

2.0 star property

Ajax

King Bed, Home Gym, 4 Tvs, Near Recreational Parks, Tennis Court, Shoping Center

A two-story house with a stone facade, a black roof, and a garage with two cars parked inside.

A modern living room with a glass coffee table, a sofa with checkered cushions, and a kitchen in the background.

A modern kitchen with white cabinetry, a marble island, and pendant lighting.

4. Dazzling Home Next to Beach & Go Station

Dazzling Home Next to Beach & Go Station

3.5 star property

West Shore

9.0 out of 10, Wonderful, (2 reviews)

9.0/10

Wonderful

(2 reviews)

"Very nice layout, large comfortable living and sleeping spaces in a great area. Short drive to all major stores, to the 401 and short walk to paths on Lake Ontario."

Lyse

Dazzling Home Next to Beach & Go Station

A living room with a sofa, a coffee table, a lamp, and a painting on the wall.

A kitchen with wooden cabinets, a microwave, a coffee maker, and a dining table with chairs.

A backyard with a swimming pool, a wooden deck, and a house.

A bedroom with a bed, pillows, a nightstand with a lamp, and a window with blinds.

5. Bungalow With Cozy 4 Bedrooms on a Large Property Lot ! Late Check-out

Bungalow With Cozy 4 Bedrooms on a Large Property Lot ! Late Check-out

2.0 star property

West Shore

Bungalow With Cozy 4 Bedrooms on a Large Property Lot ! Late Check-out

A brick fireplace with a mantel shelf displaying various items.

A kitchen with a gas stove, a microwave, and a wooden cutting board on the counter.

A bedroom with a bed, a nightstand, a lamp, and a painting on the wall.

A wooden deck with benches and a green chair.

6. Big House for Share Near 401-east And Pickering Town Centre

Big House for Share Near 401-east And Pickering Town Centre

3.0 star property

Village East

Big House for Share Near 401-east And Pickering Town Centre

7. Elegant 3-bedroom House - Bowmanville

Elegant 3-bedroom House - Bowmanville

2.0 star property

Clarington

Elegant 3-bedroom House - Bowmanville

8. Modern 3-bedroom Oshawa Home

Modern 3-bedroom Oshawa Home

2.0 star property

Eastdale

Modern 3-bedroom Oshawa Home

A laundry area with stacked washers and dryers, wooden cabinets, and a tiled backsplash.

A two-story brick house with a covered patio, a front door, and a small side window.

A dining room with a chandelier, a dining table, and six chairs.

A modern kitchen with a central island, white cabinetry, and a backsplash with grey tiles.

9. Modern Comforts, Quiet Neighborhood, Free 02 Parking

Modern Comforts, Quiet Neighborhood, Free 02 Parking

2.0 star property

Liverpool

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"House was neat and clean as showed in the pictures. We had a smooth check in process and enjoyed our stay. The house is really beautiful"

Prem

The price is RM766

RM766

RM1,013 total

includes taxes & fees

15 Oct - 16 Oct

Modern Comforts, Quiet Neighborhood, Free 02 Parking

A two-story brick house with a stone foundation, a front porch, and a driveway.

A spacious hallway with white walls, a patterned rug, and a large mirror.

A spacious living area with a dark wooden floor, a red ottoman, a blue vase, and a hexagonal mirror on the wall.

A kitchen with open wooden cabinets containing white plates, bowls, and golden mugs.

10. 4 Tvs, King Bed, Across Recreational Park, Tennis Court, Near Commercial Center

4 Tvs, King Bed, Across Recreational Park, Tennis Court, Near Commercial Center

2.0 star property

Ajax

4 Tvs, King Bed, Across Recreational Park, Tennis Court, Near Commercial Center

A dining area with a wooden table set for four, surrounded by upholstered chairs.

A modern living room with a large mirror, a clock, and potted plants.

A bedroom with a bed, a desk, a chair, a television, and a door.

A deck with a table and chairs, a red umbrella, and a view of a residential area.

11. Relaxing 4-bedroom Retreat in Bowmanville, Clarington

Relaxing 4-bedroom Retreat in Bowmanville, Clarington

2.0 star property

Clarington

The price is RM1,097

RM1,097

RM1,566 total

includes taxes & fees

15 Oct - 16 Oct

Relaxing 4-bedroom Retreat in Bowmanville, Clarington

A large brick house with a stone foundation and a prominent Eagle Glen sign.

A laundry room with a sink, two washing machines, and wooden cabinets.

A spacious living room with a large grey sofa, a coffee table, and a desk with a chair.

A bedroom with a bed, pillows, a bedside table with a lamp, and windows.

12. 4 Tvs, King Bed, Across Recreational Park, Tennis Court, Near Commercial Shops!

4 Tvs, King Bed, Across Recreational Park, Tennis Court, Near Commercial Shops!

2.0 star property

Ajax

4 Tvs, King Bed, Across Recreational Park, Tennis Court, Near Commercial Shops!

A modern kitchen with dark cabinets, a large island, and pendant lighting.

A modern kitchen with a central island, dark cabinets, and pendant lighting.

A two-story house with a garage, surrounded by snow-covered ground and trees.

13. Charming Bungalow Retreat in Whitby, Canada

Charming Bungalow Retreat in Whitby, Canada

2.0 star property

Whitby

Charming Bungalow Retreat in Whitby, Canada

A living room with a sofa, a coffee table, a TV, a fireplace, and a painting on the wall.

A kitchen with wooden cabinets, a central island with bar stools, a refrigerator, and a dining area with chairs and a table.

A bedroom with a large bed, a nightstand, a dresser, a television, and a window with curtains.

A neatly made bed with a striped bedspread, a bedside table with a lamp, and a framed picture on the wall.

14. Downtown Whitby Furnished Homes

Downtown Whitby Furnished Homes

3.5 star property

Whitby

2.0 out of 10, (1 review)

2.0/10

(1 review)

"We were selling our house so needed somewhere to stay for a week during showings. This place is clearly a short term rental run by slum lords. It was FILTHY. There were mouse droppings, spider webs, dead bugs, unknown fluids on the furniture, dead mice in traps in the kitchen and the floors were so dirty my daughter's hands and feet were black from crawling on them. We left and were promised a refund because of the conditions - well it's 2 months later and Carol the "manager" is still making up...

Michelle

Downtown Whitby Furnished Homes

15. Chic 2BR House Newly Renovated Central Spot

Chic 2BR House Newly Renovated Central Spot

2.0 star property

Ajax

Chic 2BR House Newly Renovated Central Spot

A modern kitchen with a central island, stainless steel appliances, and recessed lighting.

A spacious living area with a staircase, a dining table, two chairs, and a decorative vase.

A modern living room with a grey sofa, a coffee table, and a flat-screen TV mounted on the wall.

A modern outdoor deck with wicker furniture and a glass door leading to an interior space.

16. Lakeside Gem - Frenchman's Bay

Lakeside Gem - Frenchman's Bay

2.0 star property

Bay Ridges

Lakeside Gem - Frenchman's Bay

17. 774 Shelley Ave

774 Shelley Ave

3.0 star property

Donevan

774 Shelley Ave

A brick house with a snow-covered lawn and a clear blue sky.

A kitchen with wooden cabinets, a stainless steel sink, a white refrigerator, a microwave, and a stove.

A modern kitchen with a white stove, wooden cabinets, and a large window.

A bedroom with a bed, two bedside tables, a window, and a wall socket.

18. Comfortable Whitby 2 Bedroom Lower Suite

Comfortable Whitby 2 Bedroom Lower Suite

2.0 star property

Whitby

Comfortable Whitby 2 Bedroom Lower Suite

A modern living room with a hanging chair, a sofa, a TV, and decorative items.

A bedroom with a bed, nightstands, a dresser, and a window with curtains.

A pool table with a red felt surface, pool cues, and balls.

A modern kitchen with white cabinetry, a microwave, a refrigerator, and a sink.

19. A Very Peaceful Home

A Very Peaceful Home

2.0 star property

Pinecrest

A Very Peaceful Home

20. Spacious Whitby Haven 3BR Home Parking

Spacious Whitby Haven 3BR Home Parking

2.0 star property

Whitby

Spacious Whitby Haven 3BR Home Parking

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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Top Durham Region Hotel Reviews

Pickering Casino Resort Hotel

10/10 Excellent

"Even with the ongoing labour dispute, the hotel was clean, friendly and comfortable. Getting onto the property was relatively quick despite picketers holding cars for 5 mins and letting 5 cars in at a time. The concert venue is conveniently located as is the gambling floor."

Sean 1-night trip

Posted 14 hours ago

Pickering Casino Resort Hotel

Best Western Plus Bowmanville

8/10 Good

"Very close to the 401 and easy to get to."

Joyce 2-night trip

Posted 16 hours ago

Best Western Plus Bowmanville

Quality Suites Whitby

10/10 Excellent

"Stayed on a busy Thanksgiving Weekend. 2 nights. The property is aging but upgrades have occured and all well maintained and clean. VERY nice staff and decent choices for breakfast. Very comfy bedding. We would stay again without issue. Not a 4 star but a well run clean 3+ with a big room."

Darryl 2-night trip

Posted 1 day ago

Quality Suites Whitby

Tru By Hilton Oshawa

10/10 Excellent

"Room was very clean and breakfast was amazing."

mike 1-night trip

Posted 2 days ago

Tru By Hilton Oshawa

Travelodge by Wyndham Oshawa Whitby

8/10 Good

"NA"

Christopher 2-night trip

Posted 2 days ago

Travelodge by Wyndham Oshawa Whitby

Hilton Garden Inn Toronto/Ajax

10/10 Excellent

"Nice business hotel. Had everything we could need."

Len 1-night trip

Posted 2 days ago

Hilton Garden Inn Toronto/Ajax

Comfort Inn & Suites

8/10 Good

"Room was clean staff was exceptionally helpful"

Thomas 5-night trip

Posted 2 days ago

Comfort Inn & Suites

Courtyard by Marriott Oshawa

10/10 Excellent

"The room was very clean and comfortable. Great location and very quiet"

Kelly 1-night trip

Posted 3 days ago

Courtyard by Marriott Oshawa

Holiday Inn Express & Suites Oshawa Downtown - Toronto Area by IHG

8/10 Good

"This hotel is often used by teams. So the hallways were noisy and full of kids."

Todd 3-night trip

Posted 4 days ago

Holiday Inn Express & Suites Oshawa Downtown - Toronto Area by IHG

Find out more about Durham Region

Durham Region Private Holiday Homes information

Number of reviews	4
Accommodation	30 Private Holiday Homes
Lowest Price	RM276
Highest Price	RM1,566

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Visit Ajax
Angus Glen Golf Club
Aurora Holidays
Dentonia Park Golf Course
Duclos Point Provincial Nature Reserve
Elvis Stojko Arena
First Markham Place
Flato Markham Theatre
Visit Garden Hill
Great Blue Heron Charity Casino
Holland Marsh
Joyride 150 Indoor Bike Park
Markham Pan Am Centre
Visit Markham
Neb's Funworld
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Oshawa Holidays
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Pacific Mall
Port Hope Yacht Club
Rail Yard Wake Park
Richmond Hill Holidays
Visit Richmond Hill
Scarborough Crescent Park
Scarborough Town Centre
Seneca College - Markham Campus
Sunnybrook Hospital
Visit Agincourt
Visit Ben Jungle
Toronto Botanical Garden
Visit L'Amoreaux
Visit Riverdale
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Visit Thornhill
Visit Yonge-Eglinton
Toronto Zoo
Upper Canada Mall
Woodbine Beach

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Private Holiday Homes in Durham Region

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Durham Region holiday homes

1. Oshawa Suite Open Kitchen Living Space

2. Cozy Whitby Retreat - 2 Bedroom Private House

3. King Bed, Home Gym, 4 Tvs, Near Recreational Parks, Tennis Court, Shoping Center

4. Dazzling Home Next to Beach & Go Station

5. Bungalow With Cozy 4 Bedrooms on a Large Property Lot ! Late Check-out

6. Big House for Share Near 401-east And Pickering Town Centre

7. Elegant 3-bedroom House - Bowmanville

8. Modern 3-bedroom Oshawa Home

9. Modern Comforts, Quiet Neighborhood, Free 02 Parking

10. 4 Tvs, King Bed, Across Recreational Park, Tennis Court, Near Commercial Center

11. Relaxing 4-bedroom Retreat in Bowmanville, Clarington

12. 4 Tvs, King Bed, Across Recreational Park, Tennis Court, Near Commercial Shops!

13. Charming Bungalow Retreat in Whitby, Canada

14. Downtown Whitby Furnished Homes

15. Chic 2BR House Newly Renovated Central Spot

16. Lakeside Gem - Frenchman's Bay

17. 774 Shelley Ave

18. Comfortable Whitby 2 Bedroom Lower Suite

19. A Very Peaceful Home

20. Spacious Whitby Haven 3BR Home Parking

Find holiday rentals that suit your style

Top Durham Region Hotel Reviews

Pickering Casino Resort Hotel

Find out more about Durham Region

Durham Region Private Holiday Homes information

Explore a world of travel with Expedia