Lodging Image

Southwestern Ontario Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Southwestern Ontario holiday rentals

A covered outdoor deck with a view of a golf course.

1. The Penrose Suites

The Penrose Suites
4.0 star property
Saint Marys
9.6 out of 10, Exceptional, (37 reviews)
"Amazing property. Great experience. Will definitely be going back again soon!"
Canada
Tony
The price is S$238
includes taxes & fees
4 Oct - 5 Oct
The Penrose Suites
A spacious living area with a yellow sofa, a wooden coffee table, and a mural depicting a desert landscape.

2. The Laundry Rooms Augusta Hamilton

The Laundry Rooms Augusta Hamilton
3.0 star property
Corktown
9.4 out of 10, Exceptional, (614 reviews)
"Good communication and was able to accommodate our early check in request"
Canada
Natalie
The price is S$194
includes taxes & fees
11 Oct - 12 Oct
The Laundry Rooms Augusta Hamilton
A paved walkway with benches, a small garden area, and a view of the sea.

3. Royal Harbour Resort

Royal Harbour Resort
3.5 star property
The Blue Mountains
8.6 out of 10, Excellent, (1,004 reviews)
"fantastic stay"
Canada
John
The price is S$150
includes taxes & fees
8 Oct - 9 Oct
Royal Harbour Resort
A modern hotel lobby with a central seating area, a bar, and a TV screen.

4. Newly Built Modern Condo w Balcony & City Views

Newly Built Modern Condo w Balcony & City Views
3.5 star property
K-W Hospital
The price is S$197
includes taxes & fees
1 Oct - 2 Oct
Newly Built Modern Condo w Balcony & City Views
A modern kitchen with a marble countertop and a built-in sink, a grey sofa with cushions, and a flat-screen TV mounted on the wall.

5. Crosswinds Townhomes

Crosswinds Townhomes
3.0 star property
The Blue Mountains
9.4 out of 10, Exceptional, (27 reviews)
"We enjoyed our stay! Beautiful property"
Canada
Marianna
The price is S$361
includes taxes & fees
7 Oct - 8 Oct
Crosswinds Townhomes
An aerial view of a coastal town with a marina, residential areas, and a beach.

6. GLOBALSTAY Brand New House in Port Elgin

GLOBALSTAY Brand New House in Port Elgin
4.0 star property
Saugeen Shores
8.6 out of 10, Excellent, (64 reviews)
"Close to everything , very clean spacious and quiet , We manged but the sofa bed didn't have blanket and pillows and bed sheet,"
Canada
Faramarz
GLOBALSTAY Brand New House in Port Elgin
A modern kitchen with white cabinets, stainless steel appliances, a granite countertop, and a window providing natural light.

7. Modern 2BR Retreat w Heated Floors-gazebo

Modern 2BR Retreat w Heated Floors-gazebo
2.0 star property
Terrace Hill
The price is S$157
includes taxes & fees
12 Oct - 13 Oct
Modern 2BR Retreat w Heated Floors-gazebo
A beach with people swimming and sunbathing, a fence in the foreground, and a bicycle parked near the fence.

8. Parkside Flat #5 - Seacliff Beach Suites

Parkside Flat #5 - Seacliff Beach Suites
4.0 star property
Leamington
10.0 out of 10, Exceptional, (13 reviews)
"This is an amazing property in a great location and with the best hosts."
Canada
JANINE
The price is S$263
includes taxes & fees
1 Oct - 2 Oct
Parkside Flat #5 - Seacliff Beach Suites
A bedroom with a bed, a sofa, a dining area with chairs, and a kitchen in the background.

9. Slopeside Studio Wifi Towels Ski in Out

Slopeside Studio Wifi Towels Ski in Out
2.5 star property
Craigleith
8.0 out of 10, Very good, (3 reviews)
"Nice Little studio! Nice pool."
Canada
Kimberly
The price is S$72
includes taxes & fees
28 Oct - 29 Oct
Slopeside Studio Wifi Towels Ski in Out
A beach scene with the sun setting over the ocean, people on the sand, and a few boats in the water.

10. 2 bedroom Wiffen Cottage

2 bedroom Wiffen Cottage
3.5 star property
Ashfield-Colborne-Wawanosh
2 bedroom Wiffen Cottage
A cobblestone street lined with historic buildings, a prominent tower, and outdoor seating areas.

11. Rivergrass Condos

Rivergrass Condos
3.5 star property
The Blue Mountains
9.0 out of 10, Wonderful, (350 reviews)
"Nice place to stay."
Canada
Stephanie
The price is S$328
includes taxes & fees
7 Oct - 8 Oct
Rivergrass Condos
A beach scene with people relaxing on chairs and towels, a clear sky, and a calm sea.

12. The Shores

The Shores
3.0 star property
Saugeen Shores
7.8 out of 10, Good, (49 reviews)
"Great size place, great location - easy to walk to everything on the main strip!"
Canada
Sydney
The price is S$136
includes taxes & fees
26 Oct - 27 Oct
The Shores
A beach with a tree leaning over the sand, a clear sky, and calm water.

13. GLOBALSTAY. Waterfront 5BR Townhouse. Private HOT TUB, Gym, Sauna

GLOBALSTAY. Waterfront 5BR Townhouse. Private HOT TUB, Gym, Sauna
3.0 star property
Stoney Creek
9.0 out of 10, Wonderful, (19 reviews)
"Felt like home with enough space for 7 of us plus more. "
Canada
LEEANN
The price is S$525
includes taxes & fees
4 Oct - 5 Oct
GLOBALSTAY. Waterfront 5BR Townhouse. Private HOT TUB, Gym, Sauna
A sandy pathway leading to a beach with a clear view of the ocean and trees in the background.

14. Driftwood Haus

Driftwood Haus
3.0 star property
Saugeen Shores
9.2 out of 10, Wonderful, (109 reviews)
"Great location and all that we needed for our stay."
Canada
Saty
The price is S$214
includes taxes & fees
27 Oct - 28 Oct
Driftwood Haus
A modern kitchen with a large island, wooden bar stools, a dining table, and a view of the outside.

15. North Creek Condos

North Creek Condos
3.5 star property
Craigleith
8.4 out of 10, Very good, (203 reviews)
"Had a wonderful weekend away with my husband, the kitchen was well supplied, the space was lovely and the shuttle to the villiage was a bonus! Hit tub and pool was still open at the end of September which was a pleasant surprise and everything was clean and communication with the host was easy!"
Canada
Elizabeth
The price is S$237
includes taxes & fees
4 Oct - 5 Oct
North Creek Condos
A modern living room with a grey sofa, a round coffee table, and a dining area with a table and chairs.

16. Windsor Manor

Windsor Manor
4.0 star property
City Centre
10.0 out of 10, Exceptional, (2 reviews)
"Facility was spotless. There were no staff members on site"
Canada
Jacob
The price is S$379
includes taxes & fees
4 Oct - 5 Oct
Windsor Manor
A vanity with a mirror, a vase of flowers, and a makeup brush.

17. Serene 2-bedroom Apartment With Private Entrance and Pool Access

Serene 2-bedroom Apartment With Private Entrance and Pool Access
2.0 star property
Central Huron
The price is S$262
includes taxes & fees
26 Oct - 27 Oct
Serene 2-bedroom Apartment With Private Entrance and Pool Access
A living room with a beige sofa, a wooden ceiling beam, and a large window with blinds.

18. Ski In Ski Out Cozy Studio

Ski In Ski Out Cozy Studio
3.0 star property
Craigleith
8.8 out of 10, Excellent, (11 reviews)
"Everything is nice"
Canada
Claudia
The price is S$226
includes taxes & fees
1 Oct - 2 Oct
Ski In Ski Out Cozy Studio
A ski resort with multiple buildings, a ski slope, and a clear sky.

19. Blue Mtn 1 Bedroom with Mountain View

Blue Mtn 1 Bedroom with Mountain View
4.0 star property
Craigleith
9.2 out of 10, Wonderful, (9 reviews)
"The place was very clean and felt like your own home Close to all amenities Price was reasonable excellent place to relax and get away from Toronto busy life"
Canada
Marcello
The price is S$259
includes taxes & fees
14 Oct - 15 Oct
Blue Mtn 1 Bedroom with Mountain View
A snow-covered village with traditional wooden buildings, a ski lift, and a mountain backdrop.

20. Slopeside Loft at North Creek Resort

Slopeside Loft at North Creek Resort
4.0 star property
Craigleith
8.0 out of 10, Very good, (4 reviews)
"The property was great because it had 2 nice bathrooms. I was very disappointed that the patio was very worn and had no chairs so we couldn’t sit outside at night."
Canada
Peggy
The price is S$279
includes taxes & fees
14 Oct - 15 Oct
Slopeside Loft at North Creek Resort
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southwestern Ontario Hotel Reviews

DoubleTree by Hilton Windsor Hotel & Suites

DoubleTree by Hilton Windsor Hotel & Suites

10/10 Excellent
"Super"
Mélanie 1-night trip
Posted 1 hour ago
DoubleTree by Hilton Windsor Hotel & Suites

Explore a world of travel with Expedia