A street with a brick building, a tall tower, and a sign for 'Investor Group'.

Holiday Homes in Orillia

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Orillia holiday homes

A waterfront property with a dock, boats, and a well-lit patio area.

1. Casa Del Rosi. Unlimited Luxury in the heart of Orillia.

Casa Del Rosi. Unlimited Luxury in the heart of Orillia.
Orillia
The price is AU$2,644
includes taxes & fees
1 Sept - 2 Sept
Casa Del Rosi. Unlimited Luxury in the heart of Orillia.
A modern kitchen with white cabinetry, a stainless steel refrigerator, a microwave, an oven, and a dishwasher.

2. ❤ Getaway with an 8-seater Hot Tub ❤

❤ Getaway with an 8-seater Hot Tub ❤
Orillia
8.8 out of 10, Excellent, (3 reviews)
"Spacious and comfortable stay"
Canada
Shreya B.
The price is AU$1,312
includes taxes & fees
1 Sept - 2 Sept
❤ Getaway with an 8-seater Hot Tub ❤
A cozy outdoor sleeping area with a raised platform and a canopy, illuminated by string lights.

3. ❤ Double Delight Getaway: 2 Homes + 2 Hot Tubs ❤

❤ Double Delight Getaway: 2 Homes + 2 Hot Tubs ❤
Orillia
8.0 out of 10, Very good, (1 review)
"The house was okay for a family wedding- the beds were very comfortable- the kitchen was lacking in a few items- but it was nice to have eggs and bread good coffee and filters would have made us happier"
United States
Mary W.
The price is AU$1,870
includes taxes & fees
1 Sept - 2 Sept
❤ Double Delight Getaway: 2 Homes + 2 Hot Tubs ❤
A modern interior with a kitchen, dining area, and living room.

4. Cozy 3BR Cottage Near Lake Simcoe

Cozy 3BR Cottage Near Lake Simcoe
2.0 star property
Georgina
10.0 out of 10, Exceptional, (2 reviews)
"It was comfortable and cozy felt like home. Alot of beaches ,trails and shopping around."
Canada
Corinne
The price is AU$147
includes taxes & fees
2 Sept - 3 Sept
Cozy 3BR Cottage Near Lake Simcoe
A spacious living area with a large fireplace, a dark sectional sofa, and a staircase leading to an upper level.

5. Modern Luxury Retreat with Stunning Views & Open Concept Design

Modern Luxury Retreat with Stunning Views & Open Concept Design
severn
10.0 out of 10, Exceptional, (3 reviews)
"Amazing stay for a girls getaway weekend!"
Canada
Angue
The price is AU$807
includes taxes & fees
1 Oct - 2 Oct
Modern Luxury Retreat with Stunning Views & Open Concept Design

6. Cozy Basement Apt two bedrooms sleep 4 You can enjoy TEA & COFFEE with no charge

Cozy Basement Apt two bedrooms sleep 4 You can enjoy TEA & COFFEE with no charge
Barrie
8.0 out of 10, Very good, (1 review)
"Unit served our needs One small issue, no towels could be found Likely an oversight Other than it was a perfect layover to Georgian bay"
Canada
Patrick
Cozy Basement Apt two bedrooms sleep 4 You can enjoy TEA & COFFEE with no charge
A brick exterior with a glass door and a small outdoor seating area with a table and chairs.

7. Modern 4 Bedroom Townhouse in Barrie South

Modern 4 Bedroom Townhouse in Barrie South
Painswick
9.0 out of 10, Wonderful, (21 reviews)
"Was great!"
Canada
Patrick K.
The price is AU$340
includes taxes & fees
2 Sept - 3 Sept
Modern 4 Bedroom Townhouse in Barrie South
A wooden boardwalk through a natural area with dense vegetation and a clear sky.

8. 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, (27 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
The price is AU$439
includes taxes & fees
1 Sept - 2 Sept
Up to 40% SALE Near-Skiing-Mount Gorgeous Cottage
A spacious living area with a wooden floor, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a dining area visible through a glass door.

9. Relax in 5 Cronsberry

Relax in 5 Cronsberry
Georgina
9.8 out of 10, Exceptional, (6 reviews)
"Great house! Very clean and modern!"
United States
Nancy M.
The price is AU$227
includes taxes & fees
14 Sept - 15 Sept
Relax in 5 Cronsberry
A wooden cabin with a door, two windows, a deck, and a chair.

10. Canal Lake Cottage | Bunkie & Kayaks

Canal Lake Cottage | Bunkie & Kayaks
Kirkfield
The price is AU$434
includes taxes & fees
13 Sept - 14 Sept
Canal Lake Cottage | Bunkie & Kayaks
A wooden deck leading to a house with a star decoration, a white door, and a window.

11. Moonstone Cottage/ Ski Retreat

Moonstone Cottage/ Ski Retreat
Oro-Medonte
8.0 out of 10, Very good, (1 review)
The price is AU$465
includes taxes & fees
22 Sept - 23 Sept
Moonstone Cottage/ Ski Retreat
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.
The price is AU$263
includes taxes & fees
8 Sept - 9 Sept
Two luxury bedroom basement .
A room with a large sliding glass door leading to a deck with a view of a lake and autumn foliage.

13. Luxury Lakeview Stay with Jacuzzi | Downtown Barrie

Luxury Lakeview Stay with Jacuzzi | Downtown Barrie
Barrie
The price is AU$504
includes taxes & fees
1 Sept - 2 Sept
Luxury Lakeview Stay with Jacuzzi | Downtown Barrie
A swimming pool with inflatable toys, surrounded by a stone wall and greenery.

14. 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.
The price is AU$673
includes taxes & fees
14 Sept - 15 Sept
Lost in Hillsdale | 10 mins to Horseshoe Valley

15. Stylish 4BR Getaway. Family Friendly. Mins to Hwy

Stylish 4BR Getaway. Family Friendly. Mins to Hwy
Barrie
7.2 out of 10, Good, (7 reviews)
"Conveniently close to hwy, spacious but ad does not match the property. Cleanliness was not to expectations, bath towels were not fresh, amenities weren't all there (something as simple as garbage bags and dish towels) responsiveness was slow although friendly. It has such great potential if improvements are made."
United States
Kimberly B.
The price is AU$526
includes taxes & fees
1 Sept - 2 Sept
Stylish 4BR Getaway. Family Friendly. Mins to Hwy

16. The Kempenfelt: Luxury 4-Bedroom Forest Retreat Near Horseshoe Valley

The Kempenfelt: Luxury 4-Bedroom Forest Retreat Near Horseshoe Valley
Oro-Medonte
10.0 out of 10, Exceptional, (1 review)
"Hello Luana, Thank you for the pleasant 2 nights stay. Love the quiet location and clean rooms. Check in/out process was easy. We hope to visit again in the future. I have something to mention about washer/dryer and stove which I will message you privately. Thanks again Tsering"
Canada
tsering
The price is AU$626
includes taxes & fees
3 Sept - 4 Sept
The Kempenfelt: Luxury 4-Bedroom Forest Retreat Near Horseshoe Valley
A deck with a view of the sea and sunset.

17. Lakefront Cottage w/Hot Tub, BBQ Grill, Deck, Fire Pit, Fire Place, Sauna, Dock.

Lakefront Cottage w/Hot Tub, BBQ Grill, Deck, Fire Pit, Fire Place, Sauna, Dock.
Beaverton
9.2 out of 10, Wonderful, (79 reviews)
"The stay was lovely our group had an amazing time. The property was beautiful and clean and right on the water. The amenities were great as well we especially enjoyed using the hottub and watching the sun set over the lake."
United States
Rhea J.
The price is AU$850
includes taxes & fees
10 Sept - 11 Sept
Lakefront Cottage w/Hot Tub, BBQ Grill, Deck, Fire Pit, Fire Place, Sauna, Dock.
A modern interior with a kitchen, dining area, and living room.

18. Cozy 3BR Cottage Near Lake Simcoe

Cozy 3BR Cottage Near Lake Simcoe
Georgina
The price is AU$144
includes taxes & fees
1 Sept - 2 Sept
Cozy 3BR Cottage Near Lake Simcoe
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

19. West Oak @ Barrie H&ME Tech Build

West Oak @ Barrie H&ME Tech Build
Barrie
The price is AU$638
includes taxes & fees
14 Sept - 15 Sept
West Oak @ Barrie H&ME Tech Build
A spacious living room with a grey sofa, a wooden chair, and a coffee table. There is a dining area with a table and chairs, and a kitchen in the background.

20. Lake Simcoe Ice Fishing Basecamp • Sleeps 10–12 • Heated Shop

Lake Simcoe Ice Fishing Basecamp • Sleeps 10–12 • Heated Shop
Beaverton
Lake Simcoe Ice Fishing Basecamp • Sleeps 10–12 • Heated Shop
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 Orillia Hotel Reviews

Days Inn by Wyndham Barrie

Days Inn by Wyndham Barrie

10/10 Excellent
"The room was kept clean. Just next time more shampoo and body wash. The wallpaper in the bathroom was lifted, the shower curtain looked dirty. But all, in all it was a great room and another great stay. Will definitely come back, and recommend it to my friends and family"
Rebecca 3-night trip
Posted 6 hours ago
Days Inn by Wyndham Barrie

Find out more about Orillia

Orillia Holiday Homes information

Number of reviews
131
Accommodation
127 Holiday Homes
Lowest Price
AU$144
Highest Price
AU$1,870

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