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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.
$412 nightly
The price is $466
Oct 6 - Oct 7
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
8.8 out of 10, Excellent, (3 reviews)
"Quiet location Pool was close by Community bbq Trails nearby Nice little apartment"
Canada
Sam
$152 nightly
The price is $164
Oct 7 - Oct 8
Total with taxes and fees
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.

3. 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, (1 review)
"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
$216 nightly
The price is $236
Oct 6 - Oct 7
Total with taxes and fees
Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing
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.
$156 nightly
The price is $159
Oct 5 - Oct 6
Total with taxes and fees
Cozy 1-Bedroom Romantic Retreat with full Kitchen
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.
$240 nightly
The price is $271
Oct 15 - Oct 16
Total with taxes and fees
Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
A hot tub with multiple jets, surrounded by a wooden deck and a covered seating area with tables and chairs.

6. 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.
$477 nightly
The price is $539
Nov 1 - Nov 2
Total with taxes and fees
A cozy family retreat surrounded by trees, Nature, comfort and family memories.
A wooden boardwalk through a natural area with dense vegetation and a clear sky.

7. 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
$272 nightly
The price is $307
Oct 6 - Oct 7
Total with taxes and fees
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
An indoor swimming pool with clear views of the outside, a separate hot tub area, and a covered seating area with cushions.

8. 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
$409 nightly
The price is $462
Oct 6 - Oct 7
Total with taxes and fees
4-Bed Country Club Haven with Pool, BBQs, and More
Foyer

9. Lovely & cozy private vacation home/Cottage 3 min. walk to Beach 2

Lovely & cozy private vacation home/Cottage 3 min. walk to Beach 2
Wasaga Beach
9.4 out of 10, Exceptional, (3 reviews)
"Good clean property and host was easy to reach"
Canada
Balsam G.
$273 nightly
The price is $308
Oct 7 - Oct 8
Total with taxes and fees
Lovely & cozy private vacation home/Cottage 3 min. walk to Beach 2
A modern living room with a grey sofa, a flat-screen TV mounted on the wall, and a wooden coffee table.

10. 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
$132 nightly
The price is $149
Oct 7 - Oct 8
Total with taxes and fees
The Chieftain Suite
A staircase with wooden steps and black railings, leading to a door with glass panels.

11. Adorable 4-bedroom chalet at the edge of the forest, in Simcoe County

Adorable 4-bedroom chalet at the edge of the forest, in Simcoe County
Oro-Medonte
$514 nightly
The price is $581
Oct 5 - Oct 6
Total with taxes and fees
Adorable 4-bedroom chalet at the edge of the forest, in Simcoe County
A wooden deck with a table and chairs, overlooking a body of water with boats and buildings in the background.

12. Dock Life Beach 1 - Cottage 12, Riverview, 1 Bedroom, 3 min walk to Beach 1

Dock Life Beach 1 - Cottage 12, Riverview, 1 Bedroom, 3 min walk to Beach 1
Wasaga Beach
9.6 out of 10, Exceptional, (14 reviews)
"Clean and cute cottage just by the water with jetski rental :))"
Canada
Milan D.
Dock Life Beach 1 - Cottage 12, Riverview, 1 Bedroom, 3 min walk to Beach 1
A house with a blue door and a wooden deck.

13. The Little Lake House-Cozy 2Bdrm

The Little Lake House-Cozy 2Bdrm
Midland
9.0 out of 10, Wonderful, (8 reviews)
"Excellent!!"
Canada
Alana B.
$216 nightly
The price is $244
Nov 1 - Nov 2
Total with taxes and fees
The Little Lake House-Cozy 2Bdrm
A narrow hallway with a ceiling fan, a TV mounted on the wall, and a door leading to a bedroom.

14. Modern Tiny Wood Cottage #2 Camping style Cottages 5 minutes to the beach!

Modern Tiny Wood Cottage #2 Camping style Cottages 5 minutes to the beach!
Wasaga Beach
10.0 out of 10, Exceptional, (2 reviews)
"The cabin was amazing. Location was great and the host was so friendly. I strongly recommend to others looking for a calm getaway!"
United States
Georgia
Modern Tiny Wood Cottage #2 Camping style Cottages 5 minutes to the beach!
A modern kitchen with white cabinetry, a black refrigerator, a stove, and a microwave.

15. The Allandale Residence

The Allandale Residence
Barrie
9.8 out of 10, Exceptional, (17 reviews)
"Very nice place"
Canada
Melissa
$241 nightly
The price is $272
Oct 7 - Oct 8
Total with taxes and fees
The Allandale Residence
A poolside area with lounge chairs, striped umbrellas, and people reading magazines.

16. Sassafras Oasis | Sleeps 14 | All-Season Retreat Near Barrie

Sassafras Oasis | Sleeps 14 | All-Season Retreat Near Barrie
Minesing
8.4 out of 10, Very good, (6 reviews)
"Place was really great for a big group Not to far from places "
Canada
Tia C.
$370 nightly
The price is $418
Oct 5 - Oct 6
Total with taxes and fees
Sassafras Oasis | Sleeps 14 | All-Season Retreat Near Barrie
Beach

17. BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 8

BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 8
Wasaga Beach
9.2 out of 10, Wonderful, (24 reviews)
"Loved it second time staying and will book again"
Canada
Ryan O.
$321 nightly
The price is $372
Oct 7 - Oct 8
Total with taxes and fees
BEACHFRONT COTTAGE IN WASAGA BEACH - SANDPIPER BEACH RESORT - COTTAGE # 8
A living room with a fireplace, a television, a couch, and a small dining area.

18. 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.
$154 nightly
The price is $174
Oct 14 - Oct 15
Total with taxes and fees
Two luxury bedroom basement .
A modern living room with a TV, a round coffee table, a sofa, and a view of a cityscape through large windows.

19. 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
$189 nightly
The price is $214
Oct 7 - Oct 8
Total with taxes and fees
Stunning 1BR w Pool ~ Free Parking & Self Check-In
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 4 hours 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, 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 $307 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.