Top Vacation Homes in Durham Region in 2026

Durham Region Vacation 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

1. New Modern Home + Free Parking In Ajax

New Modern Home + Free Parking In Ajax

Ajax

8.4 out of 10, Very good, (13 reviews)

8.4/10

Very good

(13 reviews)

"Clean, convenient, and easy to check-in and out!"

Jordan

The price is HK$979

HK$979

HK$1,991 total

includes taxes & fees

3 Aug - 4 Aug

New Modern Home + Free Parking In Ajax

2 bedrooms, desk, iron/ironing board, free WiFi

2. Modern luxury suite near historic downtown Port Perry

Modern luxury suite near historic downtown Port Perry

Port Perry

9.6 out of 10, Exceptional, (9 reviews)

9.6/10

Exceptional

(9 reviews)

"Beautiful property, and amazing host!"

Brian

The price is HK$1,147

HK$1,147

HK$1,586 total

includes taxes & fees

5 Aug - 6 Aug

Modern luxury suite near historic downtown Port Perry

1 bedroom, iron/ironing board, WiFi, bed sheets

3. Cozy Ensuite Room in Oshawa

Cozy Ensuite Room in Oshawa

Taunton

Cozy Ensuite Room in Oshawa

1 bedroom, desk, iron/ironing board, free WiFi

Fridge, microwave, stovetop, electric kettle

4. Entire 1 bedroom basement suite with separate entrance in North Oshawa

Entire 1 bedroom basement suite with separate entrance in North Oshawa

Donevan

9.4 out of 10, Exceptional, (15 reviews)

9.4/10

Exceptional

(15 reviews)

"Very clean, host was excellent parking was good, kitchen could have a bigger refrigerator, freezer part of refrigerator needs to have ice removed had a scrape to get my ice packs in"

Curtis H.

The price is HK$423

HK$423

HK$1,028 total

includes taxes & fees

5 Aug - 6 Aug

Entire 1 bedroom basement suite with separate entrance in North Oshawa

Coffee/tea maker, fridge, microwave, oven

5. Brand New Luxury Entire Private Suite, Open Concept Retreat, close to everything

Brand New Luxury Entire Private Suite, Open Concept Retreat, close to everything

Ajax

10.0 out of 10, Exceptional, (16 reviews)

10/10

Exceptional

(16 reviews)

"We had a great stay at this clean, spacious and convenient property. Highly recommended it for anyone that prefers a larger accommodation over a local hotel."

Gianclaudio

The price is HK$654

HK$654

HK$980 total

includes taxes & fees

19 Aug - 20 Aug

Brand New Luxury Entire Private Suite, Open Concept Retreat, close to everything

6. Uxbridge Grand Estate - Main House on 27 Acres

Uxbridge Grand Estate - Main House on 27 Acres

Uxbridge

Uxbridge Grand Estate - Main House on 27 Acres

4 bedrooms, desk, iron/ironing board, WiFi

7. 5 minutes away from Hwy 401/Easily accessible to Toronto/close to Heber down

5 minutes away from Hwy 401/Easily accessible to Toronto/close to Heber down

Whitby

8.0 out of 10, Very good, (1 review)

8.0/10

Very good

(1 review)

"Nicely laid out. Would suit well for 4 couples. Not made for cooks. Very limited kitchen supplies. Living room, bathrooms and bedrooms all well supplied and nicely laid out.The master bath is very nice. Would stay here again."

Sandra E.

5 minutes away from Hwy 401/Easily accessible to Toronto/close to Heber down

8. Lakeside Luxe

Lakeside Luxe

Pickering

10.0 out of 10, Exceptional, (4 reviews)

10/10

Exceptional

(4 reviews)

"It is a dramatic home on a quiet street a couple of blocks from the lake. We enjoyed our stay."

Janis L.

Lakeside Luxe

9. Stunning & Bright - My home is close to the highway & Thermea Spa

Stunning & Bright - My home is close to the highway & Thermea Spa

Whitby

7.8 out of 10, Good, (6 reviews)

7.8/10

Good

(6 reviews)

"In town for OMHA finals and this was perfect. Nice and close to each arena. Host was great and quick to respond."

L M.

Stunning & Bright - My home is close to the highway & Thermea Spa

10. Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking)

Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking)

Pickering

9.2 out of 10, Wonderful, (5 reviews)

9.2/10

Wonderful

(5 reviews)

"I had a wonderful stay! The place was clean, cozy, and exactly what I needed. The host was welcoming and made everything easy. I’d definitely recommend it and would love to come back again!"

Nyajah H.

The price is HK$1,969

HK$1,969

HK$3,482 total

includes taxes & fees

4 Aug - 5 Aug

Serene Stays - Pickering (5 Beds, 2.5 Baths, 4 Parking)

11. BEACH HOUSE : FIRST FLOOR

BEACH HOUSE : FIRST FLOOR

Pickering

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"The location was wonderful and Tanika was a great host. House was clean and well organized. Definitely would book with her again!"

Mysty K.

The price is HK$564

HK$564

HK$1,256 total

includes taxes & fees

1 Sept - 2 Sept

BEACH HOUSE : FIRST FLOOR

12. Cozy Oshawa Family Escape

Cozy Oshawa Family Escape

Lakeview

9.8 out of 10, Exceptional, (6 reviews)

9.8/10

Exceptional

(6 reviews)

"The house was very clean and spacious. The host was responsive and flexible to our needs. We would stay here again."

Jennifer H.

Cozy Oshawa Family Escape

2 bedrooms, iron/ironing board, WiFi, bed sheets

13. Soft landing spot | Relaxed basement hideout

Soft landing spot | Relaxed basement hideout

Ajax

8.0 out of 10, Very good, (1 review)

8.0/10

Very good

(1 review)

"Great location and pet friendly!Host was kind and easy to communicate with.Could only see one photo on the listing- rest of property is nice.Minimal counter space in the bathroom.Only one sink/basin in kitchen, no dishwasher.Couldn't figure out to operate the dryer."

Mara S.

Soft landing spot | Relaxed basement hideout

14. Lakefront Cottage w/Hot Tub, BBQ Grill, Patio, Fire Pit, Dock, Sauna, Fire Place

Lakefront Cottage w/Hot Tub, BBQ Grill, Patio, Fire Pit, Dock, Sauna, Fire Place

Beaverton

9.2 out of 10, Wonderful, (74 reviews)

9.2/10

Wonderful

(74 reviews)

"Very nice place to stay!!!"

Derrick B.

The price is HK$2,349

HK$2,349

HK$4,803 total

includes taxes & fees

16 Aug - 17 Aug

Lakefront Cottage w/Hot Tub, BBQ Grill, Patio, Fire Pit, Dock, Sauna, Fire Place

15. Affordable stay at a friendly neighborhood. Close by Durham college

Affordable stay at a friendly neighborhood. Close by Durham college

Courtice

2.0 out of 10, (2 reviews)

2.0/10

(2 reviews)

"This listing was a nightmare - the place was disgusting and we will never come back. The only good thing was the host was responsive and issued our money back. "

muziqlistnr

The price is HK$498

HK$498

HK$923 total

includes taxes & fees

3 Aug - 4 Aug

Affordable stay at a friendly neighborhood. Close by Durham college

16. A beautiful Walkout basement

A beautiful Walkout basement

Pickering

9.6 out of 10, Exceptional, (7 reviews)

9.6/10

Exceptional

(7 reviews)

"Space was great, clean and a good location"

Chelsea

The price is HK$770

HK$770

HK$2,077 total

includes taxes & fees

1 Sept - 2 Sept

A beautiful Walkout basement

17. Green Door

Green Door

Beaverton

9.2 out of 10, Wonderful, (12 reviews)

9.2/10

Wonderful

(12 reviews)

"House was clean. Everything works. Great location. Had a great time. Would stay again. "

Todd P.

Green Door

18. Remote & peaceful 3BR/2BA Luxury Getaway on a remote farm 10 min to DT Beaverton

Remote & peaceful 3BR/2BA Luxury Getaway on a remote farm 10 min to DT Beaverton

Beaverton

9.8 out of 10, Exceptional, (6 reviews)

9.8/10

Exceptional

(6 reviews)

"The location of the house was great. A nice quiet remodeled farmhouse. Will definitely stay here again!"

Elizabeth Z.

Remote & peaceful 3BR/2BA Luxury Getaway on a remote farm 10 min to DT Beaverton

3 bedrooms, iron/ironing board, WiFi, bed sheets

19. Sleek 3 bedroom contemporary stay - close to 401, Ajax Go Station and Downtown

Sleek 3 bedroom contemporary stay - close to 401, Ajax Go Station and Downtown

Ajax

Sleek 3 bedroom contemporary stay - close to 401, Ajax Go Station and Downtown

20. Cozy 3 Bedroom Home Neighbouring Dagmar Ski Resort. Only 1 Hour from Toronto.

Cozy 3 Bedroom Home Neighbouring Dagmar Ski Resort. Only 1 Hour from Toronto.

Port Perry

10.0 out of 10, Exceptional, (8 reviews)

10/10

Exceptional

(8 reviews)

"We had a great stay! The space was clean, spacious and comfortable with all the comforts of home. Beautifully decorated on an amazing property. We were able to enjoy the sunshine on the wrap around porch and take a little nature walk. We hope to be back again soon."

Andrea B.

The price is HK$2,517

HK$2,517

HK$4,696 total

includes taxes & fees

31 Aug - 1 Sept

Cozy 3 Bedroom Home Neighbouring Dagmar Ski Resort. Only 1 Hour from Toronto.

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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