Hillsdale Vacation Rentals

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Check prices for these dates

Tonight
Dec 11 - Dec 12
Tomorrow
Dec 12 - Dec 13
This weekend
Dec 12 - Dec 14
Next weekend
Dec 19 - Dec 21

Our top choices for Hillsdale vacation rentals

Outdoor dining
The Music Shack - Outdoor Glamping Room

Vacation Home in Port McNicoll

The Music Shack - Outdoor Glamping Room
10.0 out of 10, Exceptional, (1)
"The owner was very quick to rely to questions I had Very nice cottage washroom and grounds. We had a very good stay "
Canada
Barbara M.
The price is ￥12,989
￥21,442 total
includes taxes & fees
Dec 21 - Dec 22
The Music Shack - Outdoor Glamping Room
Outdoor dining
Lovely lake view cottage home with access to a pool, firepit

Cottage in Wasaga Beach

Lovely lake view cottage home with access to a pool, firepit
9.0 out of 10, Wonderful, (2)
"My husband and I came back to Wasaga Beach for our 34 th anniversary as we stayed there for our honeymoon. The guest house was much more comfortable than the lodge we stayed at our first trip! Any employees that we met or talked to on the phone were very nice, friendly and helpful. We will definately be returning!"
United States
sarah s.
The price is ￥11,326
￥33,659 total
includes taxes & fees
Dec 12 - Dec 13
Lovely lake view cottage home with access to a pool, firepit
A heated pool
Lakefront condo steps to the beach with pool, and fireplace

Vacation Home in Wasaga Beach

Lakefront condo steps to the beach with pool, and fireplace
9.4 out of 10, Exceptional, (3)
"Clean and fun for a little getaway"
United States
Alicia T.
The price is ￥16,829
￥40,324 total
includes taxes & fees
Dec 16 - Dec 17
Lakefront condo steps to the beach with pool, and fireplace
Exterior
Modern Tiny Wood Cottage #4 Camping style Cottages 5 minutes to the beach!

Cottage in Wasaga Beach

Modern Tiny Wood Cottage #4 Camping style Cottages 5 minutes to the beach!
10.0 out of 10, Exceptional, (1)
The price is ￥15,925
￥26,674 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Modern Tiny Wood Cottage #4 Camping style Cottages 5 minutes to the beach!
Beach nearby
2 Bdrm Waterfront Retreat - Huge Beach!

Apartment in Penetanguishene

2 Bdrm Waterfront Retreat - Huge Beach!
10.0 out of 10, Exceptional, (1)
"We loved it! Ping pong table was a fun bonus."
Canada
Leslie T.
The price is ￥14,974
￥47,125 total
includes taxes & fees
Dec 14 - Dec 15
2 Bdrm Waterfront Retreat - Huge Beach!
TV, fireplace
The Chieftain Suite

Apartment in Barrie

The Chieftain Suite
9.6 out of 10, Exceptional, (11)
"Thank you for the great accommodations! Bed was super comfortable and location was perfect!"
Canada
Melanie M.
The price is ￥12,424
￥23,356 total
includes taxes & fees
Dec 15 - Dec 16
The Chieftain Suite
Property grounds
Dock Life Beach 1 - Cottage 3, Riverside 2 bedroom, 3 min walk to Beach 1

Cottage in Wasaga Beach

Dock Life Beach 1 - Cottage 3, Riverside 2 bedroom, 3 min walk to Beach 1
8.8 out of 10, Excellent, (9)
"Nice little riverside cottage. Perfect for a weekend getaway. "
Canada
Saadia
Dock Life Beach 1 - Cottage 3, Riverside 2 bedroom, 3 min walk to Beach 1
Pool
Gym+Pool+PetFriendly+KingBeds

Apartment in Shanty Bay

Gym+Pool+PetFriendly+KingBeds
9.4 out of 10, Exceptional, (3)
"It was a warm and inviting space; my older kids had a hang out area all to themselves. We had everything we needed for a week away. The pool, hot tub, and sauna were great! "
Canada
Nicole
The price is ￥15,086
￥44,436 total
includes taxes & fees
Dec 18 - Dec 19
Gym+Pool+PetFriendly+KingBeds
Terrace/patio
Modern 4 Bedroom Townhouse in Barrie South

Vacation Home in Barrie

Modern 4 Bedroom Townhouse in Barrie South
9.2 out of 10, Wonderful, (17)
"6 of my friends and I stayed here for a festival nearby and we had a good experience. Overall the house was very nice and comfortable to sleep in. Would recommend to anyone looking for a place to stay for a couple days. "
Canada
Haylee R.
The price is ￥16,208
￥38,408 total
includes taxes & fees
Dec 15 - Dec 16
Modern 4 Bedroom Townhouse in Barrie South
Fridge, microwave, oven, stovetop
Barrie house close to all amenities

Vacation Home in Barrie

Barrie house close to all amenities
9.0 out of 10, Wonderful, (29)
"Came for a kids sporting event, house was exactly as shown in listing and covered all we needed. Def would stay again."
Canada
Scotty M.
The price is ￥19,765
￥50,285 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Barrie house close to all amenities
Interior
Bright 2 Bedroom Entire Basement Apartment

Apartment in Angus

Bright 2 Bedroom Entire Basement Apartment
9.4 out of 10, Exceptional, (6)
"Very clean and bright. I would definitely stay here again. Our host was very responsive."
Canada
Robert
The price is ￥11,080
￥28,729 total
includes taxes & fees
Dec 24 - Dec 25
Bright 2 Bedroom Entire Basement Apartment
Interior
Cozy house at south end Barrie

Vacation Home in Barrie

Cozy house at south end Barrie
9.8 out of 10, Exceptional, (10)
"Excellent, clean property with all the necessary amenities. "
Canada
John
Cozy house at south end Barrie
Dining
Jacuzzi Suite Relaxing Retreat

Condo in Shanty Bay

Jacuzzi Suite Relaxing Retreat
9.4 out of 10, Exceptional, (13)
"Perfect for a night getaway. Quiet, peaceful, clean, has everything you need. "
Canada
Amy
The price is ￥12,452
￥27,854 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Jacuzzi Suite Relaxing Retreat
Marina
Friday Harbour, 2BR pet friendly

Condo in Innisfil

Friday Harbour, 2BR pet friendly
9.0 out of 10, Wonderful, (4)
"Visiting family "
Canada
Elizabeth T.
Friday Harbour, 2BR pet friendly
Exterior
Romantic Country Getaway

Condo in Shanty Bay

Romantic Country Getaway
8.8 out of 10, Excellent, (3)
"Room beautifully appointed. Property great and host very responsive. "
Canada
Jennifer
The price is ￥13,638
￥29,195 total
includes taxes & fees
Dec 14 - Dec 15
Romantic Country Getaway
Exterior
King Studio Suite – heated Pool, Sauna

Condo in Shanty Bay

King Studio Suite – heated Pool, Sauna
10.0 out of 10, Exceptional, (2)
"The suite was very clean and quiet."
Canada
Margaret
The price is ￥12,452
￥25,302 total
includes taxes & fees
Dec 23 - Dec 24
King Studio Suite – heated Pool, Sauna
Property grounds
Cheerful 4-bedroom cottage in nature setting

Cottage in Waubaushene

Cheerful 4-bedroom cottage in nature setting
10.0 out of 10, Exceptional, (2)
"What a great place if your looking for a quiet relaxing stay. Even the scenic view off the back deck, of nothing but green forest, was soooo serene. But what really put this place over the top for us, was the beds. Probably the most comfortable I've ever slept in."
United States
Jamie H.
The price is ￥39,703
￥80,572 total
includes taxes & fees
Dec 14 - Dec 15
Cheerful 4-bedroom cottage in nature setting
Beach nearby
Lake Front Family Getaway - Sandy Beach!

Apartment in Penetanguishene

Lake Front Family Getaway - Sandy Beach!
9.0 out of 10, Wonderful, (2)
"We stayed here with our 3 young boys. Check-in was easy, the place was very clean with towels and linens provided. We loved having easy access to the beach and added bonus of life jackets and kayaks/paddle boards. We didn’t get to use the fire pits but there were plenty as well as outdoor seating areas.We really enjoyed our stay and hope to come again soon! :) "
Canada
Alessia A.
The price is ￥15,742
￥48,121 total
includes taxes & fees
Dec 14 - Dec 15
Lake Front Family Getaway - Sandy Beach!
Private kitchen
The Allandale Residence

Vacation Home in Barrie

The Allandale Residence
10.0 out of 10, Exceptional, (3)
"Clean pet friendly would be pleased to stay again "
Canada
Michael P.
The price is ￥16,989
￥43,898 total
includes taxes & fees
Dec 14 - Dec 15
The Allandale Residence
Exterior
Country Retreat Horseshoe Valley

Condo in Shanty Bay

Country Retreat Horseshoe Valley
9.0 out of 10, Wonderful, (2)
"Great getaway in a quiet setting above Horseshoe Valley Resort. "
United States
David P.
The price is ￥12,452
￥25,302 total
includes taxes & fees
Dec 14 - Dec 15
Country Retreat 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

Days Inn by Wyndham Barrie

Days Inn by Wyndham Barrie

10/10 Excellent
"Yes"
Olufunke 1-night trip
Posted 7 hours ago
Days Inn by Wyndham Barrie

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?

Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage: You might want to consider this vacation home rental near Hillsdale, which is in a rural location and equipped with 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 Splashon Water Park Barrie, or get out into nature at a spot like Hardwood Ski and Bike. In the larger area, you’ll find Horseshoe Valley and Mount St. Louis Moonstone.

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.