Oakville Vacation Homes

A marina with several boats docked, including one named 'INARA'.

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Our top choices for Oakville holiday homes

A two-story house with a stone facade, a garage, and a driveway with two cars parked.

1. Designer 4BR Basement Suite – Oakville

Oakville

HK$3,391 total

includes taxes & fees

28 Oct - 29 Oct

2. Designer 4BR Basement Suite – Oakville Entire basement in Oakville, Canada

Oakville

HK$4,087 total

includes taxes & fees

28 Oct - 29 Oct

A living room with a flat-screen TV, a fireplace, a glass coffee table, a sofa, and a decorative wall piece.

3. Designer 4BR Basement Suite – Oakville

Oakville

HK$3,985 total

includes taxes & fees

28 Oct - 29 Oct

A spacious living room with a dining area, large windows, a fireplace, and a Christmas tree.

4. 5BR New Detached 4500sq Brand NewHome |13Guests | Oakville ( Creek Side Home)

Oakville

Tiffany L.

HK$5,592 total

includes taxes & fees

3 Nov - 4 Nov

A hotel room with a large bed, a mirror, a potted plant, and a wall with two circular wall art pieces.

5. Designer 4BR Basement Suite in a Detached House – Oakville

Oakville

John S.

HK$4,251 total

includes taxes & fees

3 Nov - 4 Nov

A compact kitchen with dark wood cabinets, a stainless steel range hood, a microwave, and a glass dining table with chairs.

6. Basement studio in Mississauga

Clarkson-Lorne Park

HK$884 total

includes taxes & fees

3 Nov - 4 Nov

A modern kitchen with white cabinets, stainless steel appliances, and a bar area with stools.

7. Centrally Located, Walk to Lake, Spacious | SH

Shoreacres

Chrystal B.

HK$3,052 total

includes taxes & fees

1 Nov - 2 Nov

A room with a television mounted on the wall displaying a news channel.

8. Finest BR Free Parking/Wifi TV Shared Suite

Milton

Jonathan

HK$778 total

includes taxes & fees

30 Oct - 31 Oct

A staircase with dark wooden steps and a white wall with a large abstract painting.

9. Stylish Modern Luxury Stay

Milton

Tina M.

HK$775 total

includes taxes & fees

3 Nov - 4 Nov

A modern living room with a brown sectional sofa, a small round table, and a cityscape painting on the wall.

10. Pleasant Stay Mississauga

Cooksville

Craig

HK$1,063 total

includes taxes & fees

18 Nov - 19 Nov

A bedroom with a bed, a sofa, a table, and a chair.

11. Affordable Spacious Private Suite| Ensuite Bath | Free Parking | Pearson Airport

Meadowvale Village

Eliot

HK$569 total

includes taxes & fees

6 Nov - 7 Nov

A bedroom with a bed, two bedside tables with lamps, a projector screen, and a window.

12. Luxury high rated guest apartment close to all attractions and Airport

East Credit

Tiara D.

HK$1,227 total

includes taxes & fees

28 Oct - 29 Oct

A single bed with a grey headboard, a grey blanket, and a folded towel. There is a window with a closed blind and a curtain. A cityscape painting is on the wall above the bed.

13. DT Townhouse Room Steps to Transit

Old Toronto

HK$1,254 total

includes taxes & fees

3 Nov - 4 Nov

A modern kitchen with a stainless steel refrigerator, a marble island with fruit, and a dining area with a gray sofa and table.

14. Comfortable City Home

Cooksville

Stella

HK$1,639 total

includes taxes & fees

3 Nov - 4 Nov

A modern living room with a glass dining table, white chairs, a blue sofa, and a flat-screen TV.

15. Modern private suite | Full kitchen

Hurontario

Nick K.

HK$1,120 total

includes taxes & fees

28 Oct - 29 Oct

16. King bed, Fenced Yard, Spacious New Build| GN

Watertown

Shaun P.

HK$2,870 total

includes taxes & fees

11 Nov - 12 Nov

A modern living room with a sectional sofa, a coffee table, and a patterned rug.

17. Charming 4-bedroom bungalow with Pool in soothing Mississauga

Mineola

HK$2,961 total

includes taxes & fees

28 Oct - 29 Oct

18. Elite BR, Free Parking/Wifi, TV Shared Suite

Milton

Boyd

HK$841 total

includes taxes & fees

30 Oct - 31 Oct

A kitchen with a stainless steel refrigerator, a tiled floor, and a dark wooden floor leading to a dining area.

19. 2 BR Exclusive Suite, TV, Free Parking/Wifi

Milton

HK$1,189 total

includes taxes & fees

30 Oct - 31 Oct

Three bottles of body wash and shampoo on a wall-mounted dispenser in a bathroom.

20. Beautiful 4BR Home. Wellness Room, Games, BBQ Yard

Milton

Romeo

HK$2,802 total

includes taxes & fees

2 Nov - 3 Nov

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Top Oakville Hotel Reviews

Chelsea Hotel, Toronto

8/10 Good

"Kid friendly"

Sandman Signature Mississauga Hotel

10/10 Excellent

"Rooms were clean. Bathroom counters were clean but like any other hotel, cleaning staff wipe down counters but need to rewipe. Kitchenette was well stocked. One issue was that soda machines were all the way in the basement, not even on the main floor. Even as an adult, I felt very uncomfortable going to an area that may be well-lit but creepy. Restaurant-Dennys NOT Moxies."

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