Hillsdale Vacation Rentals

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Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Hillsdale vacation rentals

Outdoor dining

Vacation Home in Port McNicoll

The Music Shack - Outdoor Glamping Room
10.0 out of 10, Exceptional, (2 reviews)
"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 ￥12,905
￥21,177 total
includes taxes & fees
Feb 2 - Feb 3
The Music Shack - Outdoor Glamping Room
Exterior

Cottage in Wasaga Beach

Modern Tiny Wood Cottage #4 Camping style Cottages 5 minutes to the beach!
10.0 out of 10, Exceptional, (1 review)
The price is ￥15,823
￥26,376 total
includes taxes & fees
Feb 1 - Feb 2
Modern Tiny Wood Cottage #4 Camping style Cottages 5 minutes to the beach!
Private kitchen

Vacation Home in Barrie

The Allandale Residence
10.0 out of 10, Exceptional, (4 reviews)
"Clean pet friendly would be pleased to stay again "
Canada
Michael P.
The price is ￥16,833
￥43,495 total
includes taxes & fees
Feb 1 - Feb 2
The Allandale Residence
A heated pool

Vacation Home in Wasaga Beach

Lakefront condo steps to the beach with pool, and fireplace
9.4 out of 10, Exceptional, (3 reviews)
"Clean and fun for a little getaway"
United States
Alicia T.
The price is ￥12,905
￥34,985 total
includes taxes & fees
Jan 30 - Jan 31
Lakefront condo steps to the beach with pool, and fireplace
Terrace/patio

Vacation Home in Barrie

Modern 4 Bedroom Townhouse in Barrie South
9.2 out of 10, Wonderful, (17 reviews)
"It was a decent place to sleep with comfortable beds. Parking very good. We were 6 guests. "
Canada
Elna S.
The price is ￥16,951
￥40,586 total
includes taxes & fees
Jan 30 - Jan 31
Modern 4 Bedroom Townhouse in Barrie South
Interior

Apartment in Angus

Bright 2 Bedroom Entire Basement Apartment
9.4 out of 10, Exceptional, (8 reviews)
"Very clean and bright. I would definitely stay here again. Our host was very responsive."
Canada
Robert
The price is ￥12,785
￥35,406 total
includes taxes & fees
Jan 30 - Jan 31
Bright 2 Bedroom Entire Basement Apartment
Interior

Vacation Home in Barrie

Cozy house at south end Barrie
9.8 out of 10, Exceptional, (10 reviews)
"Excellent, clean property with all the necessary amenities. "
Canada
John
The price is ￥14,948
￥41,112 total
includes taxes & fees
Feb 2 - Feb 3
Cozy house at south end Barrie
Property grounds

Cottage in Wasaga Beach

Dock Life Beach 1 - Cottage 3, Riverside 2 bedroom, 3 min walk to Beach 1
8.6 out of 10, Excellent, (10 reviews)
"Quiet, clean property. Owner was friendly and very helpful. We very much enjoyed our stay. Would highly reccomend."
Canada
Jasmine G.
Dock Life Beach 1 - Cottage 3, Riverside 2 bedroom, 3 min walk to Beach 1
Beach nearby

Apartment in Penetanguishene

2 Bdrm Waterfront Retreat - Huge Beach!
10.0 out of 10, Exceptional, (1 review)
"We loved it! Ping pong table was a fun bonus."
Canada
Leslie T.
The price is ￥13,822
￥45,419 total
includes taxes & fees
Feb 3 - Feb 4
2 Bdrm Waterfront Retreat - Huge Beach!
Exterior

Apartment in Shanty Bay

Garden View Suite with Jacuzzi tub & Full Kitchen
10.0 out of 10, Exceptional, (1 review)
The price is ￥12,961
￥28,342 total
includes taxes & fees
Feb 1 - Feb 2
Garden View Suite with Jacuzzi tub & Full Kitchen
Fridge, microwave, oven, stovetop

Vacation Home in Angus

Spacious 4 Bedroom House in Angus
9.4 out of 10, Exceptional, (3 reviews)
"Like i mentioned to our host it was on our top 3 list of places we stayed . The beds, livingroom and location was great. I commented to our host a few suggestion that could help in future guests. Iwould definitely recommend this location to friends and family."
Canada
Mary W.
The price is ￥18,017
￥44,833 total
includes taxes & fees
Feb 4 - Feb 5
Spacious 4 Bedroom House in Angus
Fridge, microwave, oven, stovetop

Vacation Home in Barrie

Barrie house close to all amenities
9.0 out of 10, Wonderful, (29 reviews)
"The accommodations were very comfortable and met our needs. Very close to shops and highways to access any part of the city. Quick response by host. "
Canada
Heather B.
The price is ￥18,628
￥48,694 total
includes taxes & fees
Feb 18 - Feb 19
Barrie house close to all amenities
Beach nearby

Apartment in Penetanguishene

Beachfront Apt-Patio/Huge Beach!
9.0 out of 10, Wonderful, (2 reviews)
"Very nice, we had an excellent time"
Canada
Dylan D.
The price is ￥15,344
￥47,392 total
includes taxes & fees
Feb 2 - Feb 3
Beachfront Apt-Patio/Huge Beach!
TV

Vacation Home in Wasaga Beach

Cozy beach bungalow with deck, BBQ, high-speed Wi-Fi & steps to the shoreline
8.0 out of 10, Very Good, (1 review)
The price is ￥10,998
￥32,935 total
includes taxes & fees
Feb 2 - Feb 3
Cozy beach bungalow with deck, BBQ, high-speed Wi-Fi & steps to the shoreline
A heated pool

Apartment in Wasaga Beach

Lakefront studio with shared grill & firepit - steps to beach and pool
The price is ￥9,539
￥29,110 total
includes taxes & fees
Feb 1 - Feb 2
Lakefront studio with shared grill & firepit - steps to beach and pool
Beach nearby

Apartment in Penetanguishene

Lake Front Family Getaway - Sandy Beach!
9.0 out of 10, Wonderful, (2 reviews)
"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 ￥14,583
￥46,405 total
includes taxes & fees
Feb 3 - Feb 4
Lake Front Family Getaway - Sandy Beach!
Exterior

Condo in Shanty Bay

Country Retreat Horseshoe Valley
9.4 out of 10, Exceptional, (3 reviews)
"Great getaway in a quiet setting above Horseshoe Valley Resort. "
United States
David P.
The price is ￥14,140
￥27,010 total
includes taxes & fees
Feb 1 - Feb 2
Country Retreat Horseshoe Valley
Fridge, microwave, oven, stovetop

Vacation Home in Midland

Sunnyside Stay-3bdrm w/ Gym!
9.6 out of 10, Exceptional, (8 reviews)
"Clean house. Great backyard for pets. Short drive to many things to do. Highly recommend for a family getaway."
United States
eric a.
The price is ￥15,597
￥47,678 total
includes taxes & fees
Feb 2 - Feb 3
Sunnyside Stay-3bdrm w/ Gym!
Terrace/patio

Vacation Home in Midland

The Little Lake House-Cozy 2Bdrm
8.0 out of 10, Very Good, (3 reviews)
"Excellent!!"
Canada
Alana B.
The Little Lake House-Cozy 2Bdrm
Exterior

Condo in Oro Medonte

Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
10.0 out of 10, Exceptional, (3 reviews)
"This was the perfect place for an effortless vacation with our son and his family. It is one of the cleanest places we have stayed in. The two-suite set up gave us room to gather together and privacy when needed for the younger ones. Our hosts were quick to communicate and helpful with advice on where to go for a family friendly beach. Of course, the pool was a big hit and it is nice that it was so close.A nearby grocery had everything we needed.We all commented on how comfortable the beds were...
United States
susie g.
The price is ￥16,132
￥42,577 total
includes taxes & fees
Feb 4 - Feb 5
Wildwood Hot Tub + Indoor/Outdoor Pool + Sauna + Game Room
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

10/10 Excellent
"Great Staff: Got our favorite room!"
Sandra 1-night trip
Posted 2 days ago
Monte Carlo Inn Barrie Suites

Find out more about Hillsdale

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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: Visitors like this Hillsdale vacation home rental. It 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 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.