Hillsdale 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
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Hillsdale holiday rentals

A swimming pool with inflatable toys, surrounded by a stone wall and greenery.

1. Lost in Hillsdale | 10 mins to Horseshoe Valley

Lost in Hillsdale | 10 mins to Horseshoe Valley
Hillsdale
9.4 out of 10, Exceptional, (3 reviews)
"We were a group of 8 adults. We all had our own space which was amazing! We were super close to the Vetta Spa which was fantastic. We would book this home again"
Canada
Kelly Ann
The price is AU$631
includes taxes & fees
11 Nov - 12 Nov
Lost in Hillsdale | 10 mins to Horseshoe Valley
An indoor swimming pool with a wooden ceiling, large windows, and seating areas with potted plants.

2. Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room

Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
Oro Medonte
9.8 out of 10, Exceptional, (11 reviews)
"Fantastic stay. We had great service from the host and enjoyed the design. It's easy to see that a lot of effort was put into the decor. We felt very at home and would definitely stay there again."
Canada
Travis
The price is AU$352
includes taxes & fees
26 Nov - 27 Nov
Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
A hot tub with multiple jets, surrounded by a wooden deck and a covered seating area with tables and chairs.

3. A cozy family retreat surrounded by trees, Nature, comfort and family memories.

A cozy family retreat surrounded by trees, Nature, comfort and family memories.
Oro-medonte
9.0 out of 10, Wonderful, (38 reviews)
"We had a wonderful time. Great place to stay and hope to come back again next year!Jason"
United States
Jason M.
The price is AU$687
includes taxes & fees
18 Nov - 19 Nov
A cozy family retreat surrounded by trees, Nature, comfort and family memories.
A pool area with a hot tub and seating under a covered roof.

4. Cozy 1-Bedroom Romantic Retreat with full Kitchen

Cozy 1-Bedroom Romantic Retreat with full Kitchen
Oro-Medonte
10.0 out of 10, Exceptional, (1 review)
"What a wonderful place to stay! The hose was so welcoming from the first communication and throughout the trip. The property was exactly as described but maybe even nicer in person than the pictures. The condo was super spacious with loads of room in the main room plus the bedroom. And the bathroom! Wow! Definitely spa-like with a seperate tub and shower. Treasure is comfortable to hang out on. Instructions inside for pool and wifi were clear. The bed was super comfy! And the black out curtains...
United States
Rayissa N.
The price is AU$215
includes taxes & fees
9 Nov - 10 Nov
Cozy 1-Bedroom Romantic Retreat with full Kitchen
An indoor swimming pool with clear lanes, a covered roof, and a view of the building's interior including a second floor with large windows.

5. Lovely Getaway in Nature

Lovely Getaway in Nature
Shanty Bay
7.6 out of 10, Good, (9 reviews)
"Pool, Hot Tub, Sauna and Gym were great!"
Canada
Melinda
The price is AU$208
includes taxes & fees
8 Nov - 9 Nov
Lovely Getaway in Nature
A pool area with a hot tub and seating under a covered roof.

6. Adjoining 1-Bedroom + Studio Condos near Horseshoe

Adjoining 1-Bedroom + Studio Condos near Horseshoe
Oro-Medonte
The price is AU$548
includes taxes & fees
15 Nov - 16 Nov
Adjoining 1-Bedroom + Studio Condos near Horseshoe
Exterior

7. Sassafras Oasis Sleeps 14 - All Season Retreat Near Barrie

Sassafras Oasis Sleeps 14 - All Season Retreat Near Barrie
2.0 star property
Springwater
The price is AU$595
includes taxes & fees
8 Nov - 9 Nov
Sassafras Oasis Sleeps 14 - All Season Retreat Near Barrie
A rustic barn with a sloped roof and a wooden structure with a chimney.

8. Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage

Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
Victoria Harbour
8.4 out of 10, Very good, (30 reviews)
"I recently rented a cottage for my family getaway, and I couldn't be happier with our choice! The cottage was absolutely huge, providing plenty of space for everyone to relax and enjoy our time together. One of the standout features was how clean everything was, especially the linens and towels, which were fresh and impeccably maintained. It made us feel right at home from the moment we arrived. Although the outside of the house is a bit creepy due to the vines that crawls all over the front...
Canada
Ellen
The price is AU$495
includes taxes & fees
10 Nov - 11 Nov
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
A building with a large glass facade, a swimming pool, and a picnic area.

9. 4-Bed Country Club Haven with Pool, BBQs, and More

4-Bed Country Club Haven with Pool, BBQs, and More
Oro
9.0 out of 10, Wonderful, (8 reviews)
"We stayed for 4 nights with our 3 children and had a great experience! Close to the ski hills and grocery store. Kids enjoyed the pool and games room. The room itself had everything we needed."
United States
Melissa
The price is AU$687
includes taxes & fees
19 Nov - 20 Nov
4-Bed Country Club Haven with Pool, BBQs, and More
A wooden building with a thatched roof entrance, a number '3' sign, and a Samsung air conditioning unit.

10. Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!

Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!
Wasaga Beach
8.0 out of 10, Very good, (4 reviews)
"Clean friendly easy check in and out all around great experience should recommend"
Canada
Jenna
The price is AU$270
includes taxes & fees
17 Nov - 18 Nov
Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!
A kitchen with white cabinets, a stainless steel stove, and a refrigerator.

11. Mount St Louis Cottage

Mount St Louis Cottage
Oro-Medonte
9.4 out of 10, Exceptional, (3 reviews)
"It was an amazing and fun stay! The home was perfect and the whole location itself was also peaceful. Definitely will book it again!"
United States
denise.
The price is AU$446
includes taxes & fees
11 Nov - 12 Nov
Mount St Louis Cottage
A compact kitchen with white cabinets, a black countertop, a stainless steel sink, a microwave, and a stove.

12. Dock Life Beach 1 - Unit 16, Riverside Property, 2 Bdrm, 3 min walk to Beach 1

Dock Life Beach 1 - Unit 16, Riverside Property, 2 Bdrm, 3 min walk to Beach 1
Wasaga Beach
9.0 out of 10, Wonderful, (22 reviews)
"Great location"
Canada
John
The price is AU$167
includes taxes & fees
18 Nov - 19 Nov
Dock Life Beach 1 - Unit 16, Riverside Property, 2 Bdrm, 3 min walk to Beach 1
A modern living room with a sectional sofa, a round coffee table, and a ceiling fan.

13. North Nook

North Nook
Barrie
10.0 out of 10, Exceptional, (1 review)
"Very clean and easy check in process with great communication"
Canada
Emelia
The price is AU$165
includes taxes & fees
10 Nov - 11 Nov
North Nook
A deck with a table and chairs, a Coors Light branded umbrella, and a view of a lake.

14. Hidden Gem!!!

Hidden Gem!!!
Wasaga Beach
8.2 out of 10, Very good, (24 reviews)
"We enjoyed our getaway"
Canada
Katie M.
The price is AU$603
includes taxes & fees
7 Nov - 8 Nov
Hidden Gem!!!
A modern living room with a grey sofa, a wooden coffee table, and a dining area with a table and chairs.

15. BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE UNIT # 12

BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE UNIT # 12
Wasaga Beach
9.6 out of 10, Exceptional, (43 reviews)
"It was a wonderful stay, couldnt ask for a more relaxing/beautiful spot to spend the long weekend!"
United States
Alejandro G.
The price is AU$505
includes taxes & fees
8 Nov - 9 Nov
BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE UNIT # 12
Property grounds

16. Cozy Cottage! Feels just like HOME!

Cozy Cottage! Feels just like HOME!
Wasaga Beach
8.0 out of 10, Very good, (7 reviews)
"We had a good Time. "
Canada
Manon F.
The price is AU$586
includes taxes & fees
18 Nov - 19 Nov
Cozy Cottage! Feels just like HOME!
A house with a blue door and a wooden deck.

17. The Little Lake House-Cozy 2Bdrm

The Little Lake House-Cozy 2Bdrm
Midland
9.2 out of 10, Wonderful, (10 reviews)
"Property was great. Super clean, very accurate description. Location is close to everything and good if you have others things you are doing in town or visiting people."
Canada
Danielle
The price is AU$342
includes taxes & fees
22 Nov - 23 Nov
The Little Lake House-Cozy 2Bdrm
A modern living room with a sofa, a dining table, and a kitchen area in the background.

18. Sassafras Oasis | Sleeps 14 | All-Season Retreat Near Barrie

Sassafras Oasis | Sleeps 14 | All-Season Retreat Near Barrie
Minesing
8.4 out of 10, Very good, (6 reviews)
"Place was really great for a big group Not to far from places "
Canada
Tia C.
The price is AU$573
includes taxes & fees
9 Nov - 10 Nov
Sassafras Oasis | Sleeps 14 | All-Season Retreat Near Barrie
A modern living room with a TV, a round coffee table, a sofa, and a view of a cityscape through large windows.

19. Stunning 1BR w Pool ~ Free Parking & Self Check-In

Stunning 1BR w Pool ~ Free Parking & Self Check-In
Innisfil
10.0 out of 10, Exceptional, (5 reviews)
"Although our stay was short, we had a wonderful experience. The host was excellent at communicating and made everything easy and seamless. The place was very clean, comfortable, and easily accessible. We really enjoyed our stay and would definitely love to come back!"
Canada
lisa
The price is AU$295
includes taxes & fees
8 Nov - 9 Nov
Stunning 1BR w Pool ~ Free Parking & Self Check-In
A modern hotel with a rooftop pool and outdoor seating area.

20. Upscale Spa Getaway w/ Private Sauna

Upscale Spa Getaway w/ Private Sauna
Innisfil
The price is AU$374
includes taxes & fees
15 Nov - 16 Nov
Upscale Spa Getaway w/ Private Sauna
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

Find holiday rentals that suit your style

Apartment image
Apartments
Apartments
cabin image
Cabins
Cabins

Top Hillsdale Hotel Reviews

A patio with stone seating and a fire pit, surrounded by a stone wall and greenery.
Carriage Ridge Resort, an Ascend Collection Resort

Carriage Ridge Resort, an Ascend Collection Resort

Carriage Ridge Resort, an Ascend Collection Resort
Oro-Medonte

8/10 Good

Great staff! Coffee in hand . Made to feel very welcome
Australia
Nan
Reviewed June 15, 2024
Carriage Ridge Resort, an Ascend Collection Resort

Find out more about Hillsdale

Everything you need to know about Hillsdale holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Hillsdale holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hillsdale holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Hillsdale holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hillsdale. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hillsdale holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hillsdale holiday rentals we have selected for you start as low as AU$164 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Hillsdale rentals

At Expedia, we put the best Hillsdale holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Hillsdale rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hillsdale holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hillsdale. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find holiday rentals in Hillsdale?

Yes, there are holiday rentals close to the most popular sights in Hillsdale, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Hillsdale has to offer?

Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!: This holiday home rental outside of Hillsdale is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

What can I see and do in Hillsdale?

Explore the area and family-friendly sights such as Elmvale Jungle Zoo, or get out into nature at a spot like Hardwood Ski and Bike. In the wider area, you’ll find Horseshoe Valley and Vettä Nordic Spa.

What are holiday rentals like in Hillsdale?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Hillsdale. Holiday rentals provide amenities like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of privacy away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for family trips or small group gatherings.