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Hillsdale Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Hillsdale vacation rentals

Outdoor pool

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.
$530 nightly
The price is $599
Aug 19 - Aug 20
Total with taxes and fees
Lost in Hillsdale | 10 mins to Horseshoe Valley
Front of property - evening/night

Residence & Conference Centre - Barrie

Residence & Conference Centre - Barrie
2.0 star property
Barrie
7.2 out of 10, Good, (760 reviews)
"It was very easy to access off the highway and close to where we were going!"
Canada
Nancy
$41 nightly
The price is $46
Jul 22 - Jul 23
Total with taxes and fees
Residence & Conference Centre - Barrie
Outdoor spa tub

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, (31 reviews)
"Great place to stay. Very clean and tastefully decorated. The hot tub was a nice addition. Will definitely recommend this place."
Canada
Archan M.
$603 nightly
The price is $682
Jul 20 - Jul 21
Total with taxes and fees
A cozy family retreat surrounded by trees, Nature, comfort and family memories.
Dining

Jacuzzi Suite Relaxing Retreat

Jacuzzi Suite Relaxing Retreat
Shanty Bay
9.4 out of 10, Exceptional, (24 reviews)
"The host was very accommodating and the place was very nice and exactly as described! Check in was easy and nicely laid out. "
Canada
Amanda
$162 nightly
The price is $183
Jul 26 - Jul 27
Total with taxes and fees
Jacuzzi Suite Relaxing Retreat
Pool

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, (7 reviews)
"Clean and cute condo :)Bed are very comfortable. Communication with the host was easy and informative!"
United States
Alyssa W.
$335 nightly
The price is $378
Aug 18 - Aug 19
Total with taxes and fees
Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
Exterior

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
$246 nightly
The price is $269
Jul 22 - Jul 23
Total with taxes and fees
Horseshoe Valley Resort ,KING Bd 55”Tv Spa Skiing
A heated pool

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.
$183 nightly
The price is $186
Jul 30 - Jul 31
Total with taxes and fees
Cozy 1-Bedroom Romantic Retreat with full Kitchen
Indoor pool, outdoor pool

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
$415 nightly
The price is $469
Jul 22 - Jul 23
Total with taxes and fees
4-Bed Country Club Haven with Pool, BBQs, and More
Pool

Lower Level LuxSuite - 1min Walk from Heated Pool!

Lower Level LuxSuite - 1min Walk from Heated Pool!
Shanty Bay
9.0 out of 10, Wonderful, (2 reviews)
"Clean, modern, lots of space."
Canada
Cindy S.
$262 nightly
The price is $296
Aug 10 - Aug 11
Total with taxes and fees
Lower Level LuxSuite - 1min Walk from Heated Pool!
Exterior

KingBed+Pool+HotTub+Sauna+ pet friendly

KingBed+Pool+HotTub+Sauna+ pet friendly
Oro
7.6 out of 10, Good, (4 reviews)
"The king size bed was so comfortable! My family loved the gym and the novelty of swimming in a heated pool outside surrounded by snow. Great location close to skiing and many other attractions."
Canada
Amy
$699 nightly
The price is $790
Jul 31 - Aug 1
Total with taxes and fees
KingBed+Pool+HotTub+Sauna+ pet friendly
Dining

Relax & Rejuvenate at 2BR Haven

Relax & Rejuvenate at 2BR Haven
Shanty Bay
10.0 out of 10, Exceptional, (1 review)
"Lovely stay at this unit! We have stayed at several in the complex and this was by far the nicest. Well stocked kitchen with everything we needed and beds so comfy! Would stay again!!!"
Canada
Anna
$280 nightly
The price is $316
Jul 26 - Jul 27
Total with taxes and fees
Relax & Rejuvenate at 2BR Haven
Exterior

Romantic Country Getaway

Romantic Country Getaway
Shanty Bay
8.8 out of 10, Excellent, (5 reviews)
"Room beautifully appointed. Property great and host very responsive. "
Canada
Jennifer
$172 nightly
The price is $194
Jul 26 - Jul 27
Total with taxes and fees
Romantic Country Getaway
Exterior

Hillside Haven: Serene Studio Retreat for 4

Hillside Haven: Serene Studio Retreat for 4
Oro-Medonte
9.2 out of 10, Wonderful, (5 reviews)
"Terrific stay at Hillside Haven, all of the check in, parking and checkout details were communicated clearly. The unit is well maintained and the location is great being right next to the hills and the spa. "
Canada
Natasha S.
$156 nightly
The price is $159
Jul 22 - Jul 23
Total with taxes and fees
Hillside Haven: Serene Studio Retreat for 4
Pool

Beautiful Jacuzzi Suite with Garden View/Studio

Beautiful Jacuzzi Suite with Garden View/Studio
Shanty Bay
9.0 out of 10, Wonderful, (2 reviews)
"I would have given this 4 stars but the pool was out of order. The rooms were amazing but some of the equipment was well beyond its useful lifetime (pans, towels), otherwise it would have been 5 stars. Host was excellent communicator and check in and out was easy"
Canada
Cameron
$298 nightly
The price is $337
Aug 3 - Aug 4
Total with taxes and fees
Beautiful Jacuzzi Suite with Garden View/Studio
Exterior

Hideaway 2BR Condo Pool & Heated Pool

Hideaway 2BR Condo Pool & Heated Pool
Shanty Bay
6.0 out of 10, (1 review)
$328 nightly
The price is $371
Aug 5 - Aug 6
Total with taxes and fees
Hideaway 2BR Condo Pool & Heated Pool
A heated pool

Adjoining 1-Bedroom + Studio Condos near Horseshoe

Adjoining 1-Bedroom + Studio Condos near Horseshoe
Oro-Medonte
$453 nightly
The price is $460
Aug 5 - Aug 6
Total with taxes and fees
Adjoining 1-Bedroom + Studio Condos near Horseshoe
TV, fireplace

Carriage Country Club Home Away From Home

Carriage Country Club Home Away From Home
Oro
$293 nightly
The price is $331
Aug 10 - Aug 11
Total with taxes and fees
Carriage Country Club Home Away From Home
Coffee/tea maker, fridge, microwave, oven

Lower Level @ Carriage Hills

Lower Level @ Carriage Hills
Shanty Bay
8.0 out of 10, Very Good, (7 reviews)
"The unit was fine, and close to the ski hill and Spa (just a few minute drive). Check in was easy and the host was very responsive. The amenities in the unit need updating, mostly, kitchen utensils."
Canada
John B.
$162 nightly
The price is $183
Jul 23 - Jul 24
Total with taxes and fees
Lower Level @ Carriage Hills
Exterior

King Suite – Sauna, Kitchen & heated Pool

King Suite – Sauna, Kitchen & heated Pool
Shanty Bay
8.0 out of 10, Very Good, (3 reviews)
"We were disappointed that there was a strong musty smell that was apparent as soon as we entered the door from outside that leads to the individual apartment doors. The suite had the same strong musty smell. The jets in the jetted tub were not clean. The sponge available in the kitchen smelled very badly. There was no air mattress (or pull-out couch) as per the description of the property. The fridge, kitchen, living area, bedroom and shower were clean. There was access to an apartment size...
Canada
Carolyn F.
$187 nightly
The price is $211
Jul 21 - Jul 22
Total with taxes and fees
King Suite – Sauna, Kitchen & heated Pool
Exterior

Lux Studio in Horseshoe Valley

Lux Studio in Horseshoe Valley
Oro
8.0 out of 10, Very Good, (2 reviews)
"Quiet location Pool was close by Community bbq Trails nearby Nice little apartment"
Canada
Sam
$154 nightly
The price is $167
Jul 26 - Jul 27
Total with taxes and fees
Lux Studio in Horseshoe Valley
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

Quality Inn

Quality Inn

10/10 Excellent
"Spacious room. No elevators."
VARGHESE 1-night trip
Posted 6 hours ago
Quality Inn

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 $46 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?

Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage: You might want to consider this vacation rental near Hillsdale, which is located in a rural location and offers a garden, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms and a kitchen with kitchenware.

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 Little Lake Park. 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.