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Hillsdale Vacation Rentals

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Our top choices for Hillsdale vacation rentals

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 CA $315
CA $631 total
includes taxes & fees
Nov 15 - Nov 16
Lost in Hillsdale | 10 mins to Horseshoe Valley

2. Lux Studio in Horseshoe Valley

Lux Studio in Horseshoe Valley
Oro
8.8 out of 10, Excellent, (5 reviews)
"Quiet location Pool was close by Community bbq Trails nearby Nice little apartment"
Canada
Sam
The price is CA $108
CA $221 total
includes taxes & fees
Nov 15 - Nov 16
Lux Studio in Horseshoe Valley

3. 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 CA $119
CA $330 total
includes taxes & fees
Nov 26 - Nov 27
Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room

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 CA $94
CA $213 total
includes taxes & fees
Nov 15 - Nov 16
Cozy 1-Bedroom Romantic Retreat with full Kitchen

5. 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 CA $267
CA $439 total
includes taxes & fees
Nov 12 - Nov 13
Mount St Louis Cottage

6. Respite and Relax!

Respite and Relax!
Barrie
The price is CA $89
CA $148 total
includes taxes & fees
Nov 12 - Nov 13
Respite and Relax!

7. North Nook

North Nook
Barrie
10.0 out of 10, Exceptional, (2 reviews)
"Very clean and easy check in process with great communication"
Canada
Emelia
The price is CA $124
CA $159 total
includes taxes & fees
Nov 12 - Nov 13
North Nook

8. Dock Life Beach 1 - Cottage 5, Riverside Property, 2 Bdrm, 3 min walk to Beach 1

Dock Life Beach 1 - Cottage 5, Riverside Property, 2 Bdrm, 3 min walk to Beach 1
Wasaga Beach
9.0 out of 10, Wonderful, (21 reviews)
"Third year staying with dock life. Will do again."
United States
Danielle P.
The price is CA $110
CA $149 total
includes taxes & fees
Nov 12 - Nov 13
Dock Life Beach 1 - Cottage 5, Riverside Property, 2 Bdrm, 3 min walk to Beach 1

9. 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 CA $193
CA $507 total
includes taxes & fees
Nov 12 - Nov 13
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage

10. 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 CA $145
CA $288 total
includes taxes & fees
Nov 30 - Dec 1
Stunning 1BR w Pool ~ Free Parking & Self Check-In

11. 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 CA $142
CA $236 total
includes taxes & fees
Nov 18 - Nov 19
Two luxury bedroom basement .

12. Friday Harbour Resort 2 Bedroom Pool Lake Simcoe

Friday Harbour Resort 2 Bedroom Pool Lake Simcoe
Innisfil
9.4 out of 10, Exceptional, (14 reviews)
"Check-in was easy, the apartment was clean and well equipped. Would stay again."
Canada
Albert M.
The price is CA $90
CA $246 total
includes taxes & fees
Nov 12 - Nov 13
Friday Harbour Resort 2 Bedroom Pool Lake Simcoe

13. 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 CA $176
CA $263 total
includes taxes & fees
Nov 12 - Nov 13
Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!

14. 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 CA $112
CA $333 total
includes taxes & fees
Nov 29 - Nov 30
The Little Lake House-Cozy 2Bdrm

15. Adjoining 1-Bedroom + Studio Condos near Horseshoe

Adjoining 1-Bedroom + Studio Condos near Horseshoe
Oro-Medonte
The price is CA $311
CA $545 total
includes taxes & fees
Nov 15 - Nov 16
Adjoining 1-Bedroom + Studio Condos near Horseshoe

16. Sofi House in Barrie, 5 bedroom, Pool Table, PS4, Foosball

Sofi House in Barrie, 5 bedroom, Pool Table, PS4, Foosball
The Grove
The price is CA $198
CA $606 total
includes taxes & fees
Nov 12 - Nov 13
Sofi House in Barrie, 5 bedroom, Pool Table, PS4, Foosball

17. Upscale Spa Getaway w/ Private Sauna

Upscale Spa Getaway w/ Private Sauna
Innisfil
The price is CA $179
CA $350 total
includes taxes & fees
Nov 12 - Nov 13
Upscale Spa Getaway w/ Private Sauna

18. Wasaga Daze - Unit B

Wasaga Daze - Unit B
Wasaga Beach
The price is CA $109
CA $252 total
includes taxes & fees
Nov 12 - Nov 13
Wasaga Daze - Unit B

19. Modern 4 Bedroom Townhouse in Barrie South

Modern 4 Bedroom Townhouse in Barrie South
Painswick
9.0 out of 10, Wonderful, (22 reviews)
"Great place and very responsive host."
Canada
Jason
The price is CA $123
CA $305 total
includes taxes & fees
Nov 17 - Nov 18
Modern 4 Bedroom Townhouse in Barrie South
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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Top Hillsdale Hotel Reviews

Find out more about Hillsdale

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Hillsdale. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find vacation rentals in Hillsdale?

Yes, we offer vacation rentals close to popular points of interest in Hillsdale, or you can select a secluded option if you'd like a relaxing place to stay.

What's the top vacation rental in Hillsdale?

Lake Simcoe Luxury waterfront Retreat near Friday Harbour! Hot Tub!: Visitors like this Hillsdale vacation home rental. It is located on the beach and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a 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 larger area, you’ll find Horseshoe Valley and Vettä Nordic Spa.

What are vacation rentals like in Hillsdale?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Hillsdale. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and bustling concierge desks while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.