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Hillsdale Vacation Rentals

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Check prices for these dates

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

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
9.0 out of 10, Wonderful, (2 reviews)
"Excellent accoms, as pictured, close to the slopes, would re-book & reco"
Canada
Elvira K.
The price is ￥34,837
￥73,358 total
includes taxes & fees
Oct 6 - Oct 7
Lost in Hillsdale | 10 mins to Horseshoe Valley
An indoor swimming pool with clear glass walls, a separate hot tub area, and lounge chairs along the side.

2. 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 ￥9,677
￥24,236 total
includes taxes & fees
Oct 5 - Oct 6
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.

3. 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 ￥11,956
￥25,857 total
includes taxes & fees
Oct 4 - Oct 5
Lux Studio in Horseshoe Valley
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
10.0 out of 10, Exceptional, (2 reviews)
"It was nicely furnished and decorated. I loved soaking in the bath. The balcony looked out over the woods. It felt private and peaceful."
Canada
Carly
The price is ￥19,202
￥37,078 total
includes taxes & fees
Oct 6 - Oct 7
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 ￥17,424
￥42,934 total
includes taxes & fees
Oct 12 - Oct 13
Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
A modern living room with a glass dining table, two sofas, a coffee table, and a large abstract painting.

6. Emerald &Ruby Elegant Luxury 2BR

Emerald &Ruby Elegant Luxury 2BR
Barrie
The price is ￥15,041
￥24,245 total
includes taxes & fees
Oct 7 - Oct 8
Emerald &Ruby Elegant Luxury 2BR
A modern living room with a grey sofa, a flat-screen TV mounted on the wall, and a wooden coffee table.

7. The Chieftain Suite

The Chieftain Suite
Barrie
9.6 out of 10, Exceptional, (17 reviews)
"Very clean and quiet place to stay! Communication was great and I was able to check in an hour early."
Canada
Kaitlyn
The price is ￥12,165
￥23,494 total
includes taxes & fees
Oct 4 - Oct 5
The Chieftain Suite
A wooden boardwalk through a natural area with dense vegetation and a clear sky.

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, (28 reviews)
"The place has everything you need for comfortable stay with clean big rooms and supplies. It is an Old Place with spacious and ample rooms. Doors needs some greasing and it would also help to have some light in the yard for evening. Overall experience was great."
Canada
Akhila
The price is ￥16,324
￥48,814 total
includes taxes & fees
Oct 5 - Oct 6
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
A house with a blue door and a wooden deck.

9. The Little Lake House-Cozy 2Bdrm

The Little Lake House-Cozy 2Bdrm
Midland
9.2 out of 10, Wonderful, (9 reviews)
"Excellent!!"
Canada
Alana B.
The price is ￥12,100
￥38,533 total
includes taxes & fees
Nov 1 - Nov 2
The Little Lake House-Cozy 2Bdrm
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 ￥15,333
￥27,119 total
includes taxes & fees
Nov 2 - Nov 3
Two luxury bedroom basement .
Beach

11. BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 5

BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 5
Wasaga Beach
9.6 out of 10, Exceptional, (40 reviews)
"Great little beach front cottage perfect for a family vacation! We had a great time with the kids and theyre asking to go back already!"
Canada
Hubert
The price is ￥22,119
￥58,612 total
includes taxes & fees
Oct 5 - Oct 6
BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 5
A modern lodge with a large glass facade, a waterfall feature, and a covered outdoor seating area.

12. Stylish & Modern House ♥ Walking distance to Barrie Beach!

Stylish & Modern House ♥ Walking distance to Barrie Beach!
Barrie
6.0 out of 10, (1 review)
The price is ￥12,165
￥29,993 total
includes taxes & fees
Oct 4 - Oct 5
Stylish & Modern House ♥ Walking distance to Barrie Beach!
An indoor swimming pool with clear views of the outside, a separate hot tub area, and a covered seating area with cushions.

13. 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 ￥38,597
￥72,233 total
includes taxes & fees
Oct 4 - Oct 5
4-Bed Country Club Haven with Pool, BBQs, and More
A modern living room with a wooden dining table, a sofa, and a television.

14. 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 ￥12,503
￥34,624 total
includes taxes & fees
Oct 4 - Oct 5
Bright 2 Bedroom Entire Basement Apartment
A modern hotel with a rooftop pool and outdoor seating area.

15. Upscale Spa Getaway w/ Private Sauna

Upscale Spa Getaway w/ Private Sauna
Innisfil
The price is ￥20,805
￥44,285 total
includes taxes & fees
Oct 14 - Oct 15
Upscale Spa Getaway w/ Private Sauna
A modern kitchen with white cabinetry, a black refrigerator, a stove, and a microwave.

16. The Allandale Residence

The Allandale Residence
Barrie
9.8 out of 10, Exceptional, (17 reviews)
"Very nice place"
Canada
Melissa
The price is ￥16,589
￥42,865 total
includes taxes & fees
Oct 5 - Oct 6
The Allandale Residence
Marina

17. 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 ￥14,377
￥35,741 total
includes taxes & fees
Oct 4 - Oct 5
Friday Harbour Resort 2 Bedroom Pool Lake Simcoe
A modern kitchen with white cabinets, a built-in oven, a microwave, and a window with blinds.

18. Full House, 4KM near waterfront

Full House, 4KM near waterfront
Letitia Heights
The price is ￥29,761
￥67,747 total
includes taxes & fees
Oct 3 - Oct 4
Full House, 4KM near waterfront
A glass table with a champagne bucket and glasses on a balcony with string lights.

19. 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 ￥20,805
￥46,202 total
includes taxes & fees
Oct 6 - Oct 7
Fire & Ice Spa w/ Private Sauna!
A hot tub with multiple jets, surrounded by a wooden deck and a covered seating area with tables and chairs.

20. 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 ￥44,444
￥85,251 total
includes taxes & fees
Nov 1 - Nov 2
A cozy family retreat surrounded by trees, Nature, comfort and family memories.
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
"Big room"
William 1-night trip
Posted 1 day ago
Monte Carlo Inn Barrie Suites

Find out more about Hillsdale

Search for holiday rentals in Hillsdale on Expedia! You can easily find your home rentals, villas, holiday apartments in Hillsdale using one of the methods below:

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Look no further and take a look at our great range of rental properties in Hillsdale!

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.