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Hillsdale Vacation Rentals

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
$391 nightly
The price is $442
Nov 29 - Nov 30
Total with taxes and fees
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
$144 nightly
The price is $156
Nov 16 - Nov 17
Total with taxes and fees
Lux Studio in Horseshoe Valley
A large, two-story house with a stone foundation and a symmetrical facade, featuring a central entrance with a red door and a covered porch.

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
$213 nightly
The price is $241
Nov 26 - Nov 27
Total with taxes and fees
Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
A wooden deck with Adirondack chairs and a table, overlooking a pool.

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.
$157 nightly
The price is $159
Nov 18 - Nov 19
Total with taxes and fees
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.

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.
$204 nightly
The price is $222
Nov 16 - Nov 17
Total with taxes and fees
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.
$270 nightly
The price is $305
Nov 16 - Nov 17
Total with taxes and fees
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
$93 nightly
The price is $105
Nov 16 - Nov 17
Total with taxes and fees
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
$85 nightly
The price is $97
Nov 16 - Nov 17
Total with taxes and fees
North Nook
A single-story mobile home with a covered porch, a set of concrete steps, and a small front yard.

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.
$93 nightly
The price is $105
Nov 16 - Nov 17
Total with taxes and fees
Dock Life Beach 1 - Cottage 5, Riverside Property, 2 Bdrm, 3 min walk to Beach 1
A spacious kitchen with wooden cabinets, a central island, and a dining area with chairs.

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
$525 nightly
The price is $593
Nov 16 - Nov 17
Total with taxes and fees
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
$210 nightly
The price is $237
Nov 16 - Nov 17
Total with taxes and fees
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.
$138 nightly
The price is $156
Dec 7 - Dec 8
Total with taxes and fees
Two luxury bedroom basement .
A covered outdoor area with a 'BEACH CLUB' sign, stone steps, and a view of the sea.

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.
$174 nightly
The price is $196
Nov 16 - Nov 17
Total with taxes and fees
Friday Harbour Resort 2 Bedroom Pool Lake Simcoe
Terrace/patio

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
$164 nightly
The price is $186
Nov 16 - Nov 17
Total with taxes and fees
Modern Tiny Wood Cottage #3 Camping style Cottages 5 minutes to the beach!
A house with a blue door and a wooden deck.

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
$207 nightly
The price is $233
Nov 30 - Dec 1
Total with taxes and fees
The Little Lake House-Cozy 2Bdrm
A wooden deck with Adirondack chairs and a table, overlooking a pool.

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
$378 nightly
The price is $428
Nov 16 - Nov 17
Total with taxes and fees
Sofi House in Barrie, 5 bedroom, Pool Table, PS4, Foosball
A rooftop terrace with a fire pit, hanging chairs, and a view of modern buildings.

18. Upscale Spa Getaway w/ Private Sauna

Upscale Spa Getaway w/ Private Sauna
Innisfil
$239 nightly
The price is $258
Nov 16 - Nov 17
Total with taxes and fees
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
$163 nightly
The price is $178
Nov 16 - Nov 17
Total with taxes and fees
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
$190 nightly
The price is $215
Nov 16 - Nov 17
Total with taxes and fees
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

Carriage Ridge Resort, an Ascend Collection Resort

Carriage Ridge Resort, an Ascend Collection Resort

8/10 Good
"Clean"
Ken 2-night trip
Posted less than an hour ago
Carriage Ridge Resort, an Ascend Collection Resort

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Hillsdale in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $118 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.