Default HTG hotel image

Holiday Rentals in Hillsdale

  • 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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 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
9.0 out of 10, Wonderful, (2 reviews)
"Excellent accoms, as pictured, close to the slopes, would re-book & reco"
Canada
Elvira K.
The price is €405
includes taxes & fees
18 Oct - 19 Oct
Lost in Hillsdale | 10 mins to Horseshoe Valley
An aerial view of a resort with multiple swimming pools, outdoor seating areas, and a large building with a distinctive roof.

2. Lux Studio in Horseshoe Valley

Lux Studio in Horseshoe Valley
Oro
8.8 out of 10, Excellent, (3 reviews)
"Quiet location Pool was close by Community bbq Trails nearby Nice little apartment"
Canada
Sam
The price is €151
includes taxes & fees
18 Oct - 19 Oct
Lux Studio in Horseshoe Valley
An indoor swimming pool with clear glass walls, a separate hot tub area, and lounge chairs along the side.

3. 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 €146
includes taxes & fees
28 Oct - 29 Oct
Cozy 1-Bedroom Romantic Retreat with full Kitchen
An aerial view of a resort with multiple swimming pools, outdoor seating areas, and a large building with a distinctive roof.

4. Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing

Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing
Shanty Bay
8.8 out of 10, Excellent, (3 reviews)
"Excellent place to stay while enjoying the Valley."
United States
Amy R.
The price is €215
includes taxes & fees
20 Oct - 21 Oct
Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing
An indoor swimming pool with a wooden ceiling, large windows, and seating areas with potted plants.

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

Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
Oro Medonte
9.6 out of 10, Exceptional, (10 reviews)
"It was a beautiful place. The beds were very comfortable. It had everything we needed as well. "
United States
Allison G.
The price is €244
includes taxes & fees
2 Nov - 3 Nov
Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
A wooden boardwalk through a natural area with dense vegetation and a clear sky.

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

Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
Victoria Harbour
8.6 out of 10, Excellent, (29 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 €268
includes taxes & fees
17 Oct - 18 Oct
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
A quaint building with a green exterior, a sign reading 'Weed It and Hop,' and a patio with outdoor seating.

7. Fiddlers Green at Evergreen Resort Wasaga Beach

Fiddlers Green at Evergreen Resort Wasaga Beach
Wasaga Beach
10.0 out of 10, Exceptional, (1 review)
"Jennifer provided exceptional customer service! What an incredible location and experience! We’ll be back!"
Canada
Patricia
The price is €224
includes taxes & fees
17 Oct - 18 Oct
Fiddlers Green at Evergreen Resort Wasaga Beach
A house with a blue door and a wooden deck.

8. 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 €217
includes taxes & fees
16 Nov - 17 Nov
The Little Lake House-Cozy 2Bdrm
A quaint building with a green exterior, a sign reading 'Weed It and Hop,' and a patio with outdoor seating.

9. Dockhouse at Evergreen Resort in Wasaga Beach

Dockhouse at Evergreen Resort in Wasaga Beach
Wasaga Beach
10.0 out of 10, Exceptional, (2 reviews)
"Very nice and clean property. Disappointed about the pool not being heated."
United States
Rita R.
Dockhouse at Evergreen Resort in Wasaga Beach
A living room with a fireplace, a television, a couch, and a small dining area.

10. Two luxury bedroom basement .

Two luxury bedroom basement .
Barrie
4.0 out of 10, (2 reviews)
"We were not allowed in to the apartment due to a plumbing issue. A plumber was coming but we were not contacted when the problem was fixed. We found other accommodation so we could get to the show we were in town for. All attempts to reach the host were ignored. It has taken 10 days and 5 Vrbo agents to hopefully get a refund.This has left a very negative experience for using vrbo. I have always been very happy with vrbo, but it will be a while before I use them again. The support team from vrbo...
United States
Judy L.
The price is €155
includes taxes & fees
16 Nov - 17 Nov
Two luxury bedroom basement .
Interior

11. 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 €362
includes taxes & fees
25 Oct - 26 Oct
Sassafras Oasis Sleeps 14 - All Season Retreat Near Barrie
Marina

12. Friday Harbour Resort 2 Bedroom Pool Lake Simcoe

Friday Harbour Resort 2 Bedroom Pool Lake Simcoe
Innisfil
9.4 out of 10, Exceptional, (13 reviews)
"Check-in was easy, the apartment was clean and well equipped. Would stay again."
Canada
Albert M.
The price is €207
includes taxes & fees
18 Oct - 19 Oct
Friday Harbour Resort 2 Bedroom Pool Lake Simcoe
A modern hotel with a rooftop pool and outdoor seating area.

13. Upscale Spa Getaway w/ Private Sauna

Upscale Spa Getaway w/ Private Sauna
Innisfil
The price is €253
includes taxes & fees
19 Oct - 20 Oct
Upscale Spa Getaway w/ Private Sauna
A glass table with a champagne bucket and glasses on a balcony with string lights.

14. Fire & Ice Spa w/ Private Sauna!

Fire & Ice Spa w/ Private Sauna!
Innisfil
10.0 out of 10, Exceptional, (13 reviews)
"Great views in a warm, fire-lit setting—perfect spot for a night out."
Canada
Craig
The price is €264
includes taxes & fees
18 Oct - 19 Oct
Fire & Ice Spa w/ Private Sauna!
A modern living room with a wooden dining table, a sofa, and a television.

15. Bright 2 Bedroom Entire Basement Apartment

Bright 2 Bedroom Entire Basement Apartment
Angus
9.0 out of 10, Wonderful, (13 reviews)
"Great place"
United States
Adriano A.
The price is €201
includes taxes & fees
18 Oct - 19 Oct
Bright 2 Bedroom Entire Basement Apartment
An indoor swimming pool with clear views of the outside, a separate hot tub area, and a covered seating area with cushions.

16. 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 €457
includes taxes & fees
26 Oct - 27 Oct
4-Bed Country Club Haven with Pool, BBQs, and More
A marina at dusk with boats docked, waterfront buildings, and a calm water surface reflecting the lights.

17. Oasis Spa w/ Private Sauna!

Oasis Spa w/ Private Sauna!
Innisfil
10.0 out of 10, Exceptional, (1 review)
"The Oasis Spa Getaway was a fantastic two night stay for my partner and I. The property was clean, modern and cozy! The unit had everything a couple needs for their stay including a sauna within the unit and a beautiful balcony. The host Michelle provided exceptional hospitality and was easy to connect with when needed. The location is great and only a short walk to the boardwalk and a quick two minute drive to the Nest golf course. The building’s pool was easy to access, quiet, and relaxing....
Canada
Matthew K.
The price is €244
includes taxes & fees
18 Oct - 19 Oct
Oasis Spa w/ Private Sauna!
A modern living room with a TV, a round coffee table, a sofa, and a view of a cityscape through large windows.

18. 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, (3 reviews)
"This place was immaculate. Host was always super responsive. Had everything we needed. Highly recommend. We really enjoyed our stay."
Canada
Jennifer
The price is €195
includes taxes & fees
18 Oct - 19 Oct
Stunning 1BR w Pool ~ Free Parking & Self Check-In
A hot tub with multiple jets, surrounded by a wooden deck and a covered seating area with tables and chairs.

19. 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, (36 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 €441
includes taxes & fees
1 Nov - 2 Nov
A cozy family retreat surrounded by trees, Nature, comfort and family memories.
A swimming pool with a surrounding deck, a covered seating area, and a view of the ocean.

20. Wasaga Daze - Unit B

Wasaga Daze - Unit B
Wasaga Beach
The price is €226
includes taxes & fees
19 Oct - 20 Oct
Wasaga Daze - Unit B
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 Hillsdale Hotel Reviews

Travelodge by Wyndham Barrie

Travelodge by Wyndham Barrie

8/10 Good
"My husband and I had a very nice stay at the Travelodge in Barrie Ontario, Canada The room we had was very clean.. The only thing I would have them check out the water in the bath tube as we were showering the water was filling up in the bath tube my husband said they need to clean the drain. Staff was very nice.. Breakfast was good needs a change up maybe one day sausages and eggs next day bacon and eggs...Parking was good plenty of it.. I would recommend this Motel to anyone who wanted to go and stay there. Thanks Joanne"
Joanne 2-night trip
Posted 1 hour ago
Travelodge by Wyndham Barrie

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, apart-hotels, 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 favorite 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 depends 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 €151 per night. Entering your travel dates in the search wizard you might find 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.