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Hillsdale Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Hillsdale vacation 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 CA $315
CA $631 total
includes taxes & fees
Nov 29 - Nov 30
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
9.0 out of 10, Wonderful, (6 reviews)
"Quiet location Pool was close by Community bbq Trails nearby Nice little apartment"
Canada
Sam
The price is CA $108
CA $223 total
includes taxes & fees
Nov 16 - Nov 17
Lux Studio in Horseshoe Valley
An indoor swimming pool with a wooden ceiling, large windows, and seating areas with potted plants.

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 $129
CA $342 total
includes taxes & fees
Nov 26 - Nov 27
Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
An indoor swimming pool with clear glass walls, a separate hot tub area, and lounge chairs along the side.

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 $106
CA $227 total
includes taxes & fees
Nov 18 - Nov 19
Cozy 1-Bedroom Romantic Retreat with full Kitchen
A modern living room with a black sofa, a coffee table, and a patterned rug. There is a kitchen area with a bar and seating.

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

Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing
Shanty Bay
7.6 out of 10, Good, (4 reviews)
"Excellent place to stay while enjoying the Valley."
United States
Amy R.
The price is CA $174
CA $314 total
includes taxes & fees
Nov 16 - Nov 17
Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing
A kitchen with white cabinets, a stainless steel stove, and a refrigerator.

6. 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 $266
CA $437 total
includes taxes & fees
Nov 16 - Nov 17
Mount St Louis Cottage
A living room with a grey sofa, a patterned rug, and a glass door leading to a balcony.

7. Respite and Relax!

Respite and Relax!
Barrie
The price is CA $89
CA $149 total
includes taxes & fees
Nov 16 - Nov 17
Respite and Relax!
A modern living room with a sectional sofa, a round coffee table, and a ceiling fan.

8. 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 $104
CA $138 total
includes taxes & fees
Nov 16 - Nov 17
North Nook
A small, neatly arranged room with a bed, a desk, a chair, and a television mounted on the wall.

9. 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 $150 total
includes taxes & fees
Nov 16 - Nov 17
Dock Life Beach 1 - Cottage 5, Riverside Property, 2 Bdrm, 3 min walk to Beach 1
A wooden boardwalk through a natural area with dense vegetation and a clear sky.

10. 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 $470
CA $846 total
includes taxes & fees
Nov 16 - Nov 17
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
A modern living room with a TV, a round coffee table, a sofa, and a view of a cityscape through large windows.

11. 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 $185
CA $334 total
includes taxes & fees
Nov 16 - Nov 17
Stunning 1BR w Pool ~ Free Parking & Self Check-In
A living room with a fireplace, a television, a couch, and a small dining area.

12. 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 $140
CA $223 total
includes taxes & fees
Dec 7 - Dec 8
Two luxury bedroom basement .
Marina

13. 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 $108
CA $278 total
includes taxes & fees
Nov 16 - Nov 17
Friday Harbour Resort 2 Bedroom Pool Lake Simcoe
A wooden building with a thatched roof entrance, a number '3' sign, and a Samsung air conditioning unit.

14. 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 $264 total
includes taxes & fees
Nov 16 - Nov 17
Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!
A modern living room with a grey sofa, a coffee table, and two armchairs. There is a kitchen area with a microwave and a coffee machine. A wooden bar counter with stools is visible.

15. 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 30 - Dec 1
The Little Lake House-Cozy 2Bdrm
An indoor swimming pool with clear glass walls, a separate hot tub area, and lounge chairs along the side.

16. Adjoining 1-Bedroom + Studio Condos near Horseshoe

Adjoining 1-Bedroom + Studio Condos near Horseshoe
Oro-Medonte
Adjoining 1-Bedroom + Studio Condos near Horseshoe
An outdoor patio with a wooden deck, white chairs, and string lights.

17. 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 $609 total
includes taxes & fees
Nov 16 - Nov 17
Sofi House in Barrie, 5 bedroom, Pool Table, PS4, Foosball
A modern hotel with a rooftop pool and outdoor seating area.

18. Upscale Spa Getaway w/ Private Sauna

Upscale Spa Getaway w/ Private Sauna
Innisfil
The price is CA $179
CA $368 total
includes taxes & fees
Nov 16 - Nov 17
Upscale Spa Getaway w/ Private Sauna
A snow-covered beach with steps leading down to the water, a railing, and a bench.

19. Wasaga Daze - Unit B

Wasaga Daze - Unit B
Wasaga Beach
The price is CA $109
CA $253 total
includes taxes & fees
Nov 16 - Nov 17
Wasaga Daze - Unit B
A brick exterior with a glass door and a small outdoor seating area with a table and chairs.

20. 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 16 - Nov 17
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

Monte Carlo Inn Barrie Suites

Monte Carlo Inn Barrie Suites

8/10 Good
"I like Monte Carlo hotels anywhere I go but may I say that the Barrie one was fine but the one in Vaughn Ontario is much better … the Barrie site requires updating and upgrading … also may we have at least 3 bath towels and 2 coffee pods for 2 people … also … Vaughn had everything I asked for … as wine glasses … sorry for being so picky but at the present price of hotel rooms I would like ALL to have the same standards . … thank you for listening !"
Pauline 1-night trip
Posted 1 hour ago
Monte Carlo Inn Barrie Suites

Find out more about Hillsdale

Everything you need to know about Hillsdale vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hillsdale vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Hillsdale vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hillsdale vacation rentals we have selected for you start as low as CA $169 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 vacation 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 vacation.

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 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.