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Holiday rentals in Oro-Medonte

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Top-rated holiday rentals in Oro-Medonte

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest suite in Moonstone

4.83 out of 5 average rating, 161 reviews

SKI, Trails HOT TUB and SAUNA in the woods

PLEASE READ! Mt. St. Louis & Horseshoe Valley at doorstep! This is a bright, large and private walk-out GUEST SUITE (basement apartment). Hot tub, patio, fire pit & secluded path in the woods to enjoy nature. Kitchen is equipped with an induction cooktop and all things necessary, even wine bottle opener:) Open concept living room/kitchen/dining room with TV & Roku. Bedroom is a work of Art: dark, mysterious and romantic! Custom Queen bed made from weathered barn wood salvaged from our property.

12–17 May

$172 SGD per night

Guest favourite

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 208 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

24 Feb – 3 Mar

$162 SGD per night

Guest favourite

Place to stay in Wasaga Beach

5.0 out of 5 average rating, 190 reviews

Newly Built Woodsy Loft Retreat

Welcome to Woodsy Loft, a newly built retreat. A great spot for a getaway! A perfect home base for not just the beach and stunning walks into the sunset, but Blue Mtn, Scandinavian Spa, Collingwood, Cross Country Skiing Provincial Park and a brand new casino, all close by. Packed with amenities like screened in patio, XL bathtub, King size bed, 'The Frame' Smart TV, full kitchen, fast WIFI, motorized blind...and the list goes on. Situated and designed to offer max. privacy and relaxation.

16–23 Sep

$192 SGD per night

Guest favourite

Apartment in Innisfil

4.97 out of 5 average rating, 111 reviews

•#TheFridayFlat Luxury Poolside Retreat for Summer

Enjoy access to all of Friday Harbour's world-class amenities, including a golf course and sandy beach. Take a dip in the outdoor pool and explore the kilometres of scenic walking trails that wind through the Nature Preserve Located just a short drive from Toronto, Friday Harbour offers the perfect escape from city life. Spend your days exploring the shops and restaurants of the promenade, or venture out onto the lake. Come experience the ultimate waterfront getaway at Friday Harbour!

21–28 Sep

$150 SGD per night

Guest favourite

Guest suite in Oro Medonte

5.0 out of 5 average rating, 52 reviews

Hilltop Suite, a lovely 2 Bedroom Suite

Welcome to The Hilltop Suite! Located in the heart of Horseshoe Valley, our cozy retro style suite is the perfect location for your getaway and to enjoy a fun relaxing stay. The Hilltop Suite is 3 minutes away from Horseshoe Valley Ski Resort home of skiing, tubing, golfing, treetop trekking. The famous Vetta Spa is 5 minutes away. We are 20 minutes away from both Barrie and Orillia, where you can check out Downtown Barrie's beautiful waterfront with an array of restaurant's and shops.

24 Sep – 1 Oct

$105 SGD per night

Guest favourite

Apartment in Shanty Bay

4.92 out of 5 average rating, 12 reviews

Resort Condo near Horseshoe Valley

Enjoy a stylish experience in this spacious and serene space at Carriage Country Club Resort. A completely equipped designer suite for families looking for the perfect vacation. Enjoy a peaceful night in your private Jacuzzi , prepare your own meal in the fully equipped kitchen. Few minutes drive to Horseshoe Valley Resort, and walkable to Vettä Nordic Spa. For Mount St. Louis Moonstone, only about 15 minutes drive away. Our heated indoor/outdoor swimming pool, available year-round.

7–14 May

$133 SGD per night

Guest favourite

Flat in Orillia

4.94 out of 5 average rating, 141 reviews

Your Downtown *Hot Tub* Getaway!

This Incredible unit is the perfect blend of style, luxury & convenience. Filled With all the amenities you look for with the touch of luxury that you would expect in a hotel. Spend your evenings relaxing with a glass of wine in the private hot tub area, immersing yourself in the cinematic feel of the 65" TV, or walking through the bustling downtown streets of Orillia on the way to catch the sunset at the waterfront. However you choose to spend your stay, there is much to enjoy! 🤩

11–18 Sep

$159 SGD per night

Guest favourite

Apartment in Oro

4.9 out of 5 average rating, 116 reviews

4-Bed Country Club Haven with Pool, BBQs, and More

Welcome to our one-of-a-kind 4-bed condo country club, an exceptional destination that caters to large families and offers an unforgettable vacation experience. This uniquely structured property features two separate bedroom suites, with Wi-Fi and a range of outstanding amenities, your every need will be catered to. Dive into the ultimate aquatic experience with our heated indoor/outdoor pool, indulge in the benefits of our sauna, and melt away your cares in the inviting hot tub.

6–13 Jan

$216 SGD per night

Guest favourite

Townhouse in Shanty Bay

5.0 out of 5 average rating, 28 reviews

Stylish Town For 5, Ravine Backyard, Resort Pool

Forget your worries in this spacious and serene space at Carriage Country Club Resort. You get a full designer suite perfect for couples, equipped with a King Sized Bed, and a Jacuzzi for romantics. Prepare your own meals in the fully equipped kitchen with Microwave and Electric Stove. Access your favorite Streaming-TV accounts like Netflix, Prime, and Disney+ Close to Vetta Spa! Dual Indoor and Heated Outdoor Pool; literally the Best Retreat in Oro-Medonte. Book with Us Today!

30 Nov – 7 Dec

$123 SGD per night

Guest favourite

Flat in Orillia

4.96 out of 5 average rating, 111 reviews

DaVel DeLuxe Garden view.

Read our revues and judge for yourself. Large one bedroom apartment in newly built addition to a beautiful historic house. Only few minutes walk to downtown, shops, restaurants, cafes, and the lakefront. Vetta Spa and Horseshoe skiing is 10-15 minutes away. We know that your health and safety is of paramount importance, and we take extreme measures to clean and disinfect the place as best as possible before every guest. Many guests enjoyed our place and visit again and again.

18–25 Sep

$156 SGD per night

Guest favourite

Dome in Hawkestone

4.94 out of 5 average rating, 238 reviews

Glen Oro Eco-Retreat Glamping Stargazer Dome

Leave the noise and rush of the modern world behind, unplug from your normal routine and immerse yourself in a beautiful old growth hardwood forest. Our Eco-Retreat focuses on providing a luxurious platform for you to stay in all the comforts of a boutique hotel amidst the raw and natural beauty of our Canadian wilderness. Here at Glen Oro we have over 200 acres of rolling fields and forests, horseback riding, hiking trails, and an incredible starry night sky.

26 Dec – 2 Jan

$508 SGD per night

Guest favourite

Apartment in Oro

4.9 out of 5 average rating, 154 reviews

Spacious 1-br w pool & jacuzzi at Horseshoe Valley

Welcome to Horseshoe Valley, just 1.5 hrs north of Greater Toronto Area. It's a four-season wonder of nature with limitless access to lakes, rivers, trails, and rolling hills. Whether you aim to ski in snow-laden forests of pine, hit golf at one of eighteen golf courses, mountain bike or hike in several landscape trails, soak in the healing experience of Vetta Nordic spa, or simply relax at the tranquility of the area, this place is simply yours to enjoy!

6–13 Oct

$137 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Bungalows

Intimate homes, inviting architecture

Houses

A space that's all yours, with room for everyone

Chalets

Adventure-ready homes with après-ski style

Popular amenities for Oro-Medonte holiday rentals

Free parking on premises

Air conditioning

Stay near Oro-Medonte's top sights

Sibbald Point Provincial Park51 locals recommend

Innisfil Beach Park87 locals recommend

Costco Wholesale10 locals recommend

Couchiching Beach Park94 locals recommend

Friday Harbour Resort95 locals recommend

Centennial Beach36 locals recommend

Other great holiday rentals in Oro-Medonte

Guest favourite

Apartment in Oro

4.95 out of 5 average rating, 78 reviews

Pet-friendly, 1 BR condo in Horseshoe Valley

20–27 Dec

$161 SGD per night

Guest favourite

Home in Hawkestone

4.93 out of 5 average rating, 54 reviews

Lakeside Cottage Getaway

8–15 Dec

$183 SGD per night

Guest favourite

Apartment in Oro

4.93 out of 5 average rating, 27 reviews

Stunning Suite in Horseshoe Valley

29 Mar – 5 Apr

$158 SGD per night

Guest favourite

Apartment in Oro

4.93 out of 5 average rating, 30 reviews

Cozy 1-Bedroom Romantic Retreat with full Kitchen

25 Sep – 2 Oct

$128 SGD per night

Guest favourite

Loft in Midhurst

5.0 out of 5 average rating, 36 reviews

Loft - Ski - Hike - Swim - Relax

8–15 May

$134 SGD per night

Guest favourite

Cabin in Hawkestone

4.94 out of 5 average rating, 17 reviews

Blue Dreams Of Lake Simcoe

27 Sep – 4 Oct

$152 SGD per night

Apartment in Oro

4.9 out of 5 average rating, 40 reviews

Carriage Country Club Home Away From Home

2–9 Sep

$183 SGD per night

Guest favourite

Place to stay in Oro Station

4.96 out of 5 average rating, 55 reviews

The Bunkie- A Cozy Modern Escape

5–12 Jun

$183 SGD per night

Quick stats about holiday rentals in Oro-Medonte

Total rentals
2.1K properties
Rentals with dedicated workspaces
1.1K properties have a dedicated workspace
Rentals with a pool
430 properties have a pool
Pet-friendly rentals
730 properties allow pets
Family-friendly rentals
1.3K properties are a good fit for families
Total number of reviews
60K reviews

Destinations to explore