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Vacation rentals in Hillsdale

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Top-rated vacation rentals in Hillsdale

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Guest suite in Moonstone

4.83 out of 5 average rating, 164 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.

May 13 – 18

G$26,880 GYD per night

Dome in Bradford West Gwillimbury

4.98 out of 5 average rating, 216 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...

Apr 3 – 10

G$24,990 GYD per night

Place to stay in Wasaga Beach

5.0 out of 5 average rating, 195 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.

Nov 30 – Dec 7

G$30,503 GYD per night

Apartment in Penetanguishene

4.88 out of 5 average rating, 380 reviews

The Haunted House Apt 302

As you pull into the driveway this 1885 Victorian towers above you, your mouth drops in awe of the size. Up the porch to enter a small front door, a dimly lit winding staircase creaks as you ascend to 3rd floor. Original architecture painted many times over oozes with history. 70 years ago the house was turned into apartments, unloved for many of those years, time has definately taken its tole, yet to the spirits within, their big old house still stands proud and distinguished in all its glory.

Apr 22 – 29

G$26,600 GYD per night

Apartment in Wasaga Beach

4.95 out of 5 average rating, 339 reviews

The Upper Deck

The upper deck is an amazing one bedroom studio with a full newly renovated bathroom, a sweet kitchenette, an amazing king size bed, a 65 “ inch HD smart Samsung TV with a live edge counter- a great workspace or eating area. One wall is floor to ceiling windows -lots of great natural light!!! Outdoors has an amazing hot tub , rustic firepit area , a beautiful covered outdoor eating area with Bbq and you can hear the lake!! Note- the studio is a separate but is part of a house.

Feb 28 – Mar 7

G$27,758 GYD per night

Guest suite in Phelpston

4.96 out of 5 average rating, 185 reviews

Country Escape/Private bright lower/2 Bdrm Suite

A totally separate private basement Apt. Large windows with 9’ ceilings, private entrance through the garage. Perfect for a couple or small family getaway. Max is a family of 4. Private patio area, plus full access to backyard. Two comfy bedrooms with queen beds. Spa bathroom with large shower. Large open concept Living area, Game area and KITCHENETTE Roku 75”TV Extra Large driveway Pool available in May. Surrounded by Ski Resorts, Beaches, Trails and Vetta Nordic Spa.

Jul 19 – 26

G$34,918 GYD per night

Guesthouse in Tiny

5.0 out of 5 average rating, 109 reviews

Welcome to the Wood Road House

This 485 sq ft garage conversion will be sure to make you feel at home. Complete with one queen sized bed, and sofa bed, it suits well to a couple or small family. Open the garage door to have sunsets land on your front step, and oversized patio doors allow you to have the outside come in. Cozy up to a gas fireplace, while catching a movie or enjoying a glass of wine. Enjoy calm and quiet nature in this private space, that allows tranquility in a country setting.

May 11 – 18

G$21,493 GYD per night

Guest suite in Barrie

4.91 out of 5 average rating, 105 reviews

"Chalet TEN" an exclusive Horseshoe Valley retreat

This is TEN: a private guest suite in our bespoke timber chalet, nestled amongst the trees. With soaring views of Horseshoe Resort through the panoramic windows a mere moment away- the chairlifts, restaurants, bars, and day spas are at your fingertips. The definition of style and comfort, TEN is the best destination for a romantic weekend in the trees or people looking for a designer retreat, tailor-made to suit. Welcome to TEN, your greatest escape awaits!

Sep 4 – 11

G$34,771 GYD per night

Guesthouse in Victoria Harbour

4.98 out of 5 average rating, 229 reviews

Sunset Beach Cottage

Part log treehouse, part beach house and 100% of what you need to enjoy a peaceful getaway only 1.5 hours from Toronto! Walk up the private staircase and pause to enjoy the spectacular treetop and waterfront views from your own wraparound deck before entering your 900 sq. ft. oasis. Enjoy access to your own lawn, picnic table and beach* area and all that Georgian Bay and the area has to offer. *water levels fluctuate Insta: sunset_beach_cottage_canada

Oct 21 – 28

G$36,855 GYD per night

Cottage in Torrance

4.97 out of 5 average rating, 196 reviews

Beautiful Nine Mile Lake

Beautiful Muskoka getaway! Newly renovated 4 season waterfront cottage! Stunning views! Located on picturesque Nine Mile Lake. Over 70% of the lake is crown land. Perfect for kayaking and canoeing to enjoy all the beauty Muskoka is known for. We have kayaks a canoe and a paddle board for you to enjoy. Plenty of sun exposure on the dock you can swim all day long. Close to hiking and snowmobile trails. May 15-Oct 2 Minimum 6 nights with a Sunday check in.

May 20 – 25

G$34,912 GYD per night

Condo in Oro

4.9 out of 5 average rating, 157 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!

Oct 18 – 25

G$20,685 GYD per night

Cottage in Tiny

4.95 out of 5 average rating, 196 reviews

Private 40 Acre Cottage with Hot Tub

Our two bedroom cabin + cubby (available in summers) by a scenic pond is a private getaway while close to the main road and many amenities. Private outdoor space includes hot tub, deck, fire pit, and walking trails. We have a barn with ping pong and foosball tables. We are 20 min to Barrie, 10 min to Midland, 20 min to Balm beach, Wasaga beach, Mt. St Louis and Horseshoe Valley resort.

Sep 7 – 14

G$73,100 GYD per night

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Air conditioning

Other great vacation rentals in Hillsdale

Cottage in Port McNicoll

4.98 out of 5 average rating, 126 reviews

Boe's Cottage: Newly Renovated - Great WIFI

Oct 30 – Nov 6

G$22,640 GYD per night

Guest suite in Oro Medonte

5.0 out of 5 average rating, 58 reviews

Hilltop Suite, a lovely 2 Bedroom Suite

Apr 3 – 10

G$21,971 GYD per night

Apartment in Shanty Bay

4.93 out of 5 average rating, 28 reviews

Spacious Hideaway in Nature

Oct 22 – 29

G$10,050 GYD per night

Home in Elmvale

4.86 out of 5 average rating, 21 reviews

Rustic & Relaxed Cabin

Mar 30 – Apr 6

G$29,768 GYD per night

Guesthouse in Shanty Bay

4.85 out of 5 average rating, 81 reviews

New Charming tinyhome Experience

May 15 – 22

G$13,844 GYD per night

Guesthouse in Shanty Bay

4.99 out of 5 average rating, 89 reviews

The Guest House, Maplewood Hills

May 20 – 27

G$35,065 GYD per night

Condo in Shanty Bay

4.87 out of 5 average rating, 15 reviews

Resort Condo near Horseshoe Valley, Jacuzzi+Pool

Sep 30 – Oct 7

G$23,263 GYD per night

Townhouse in Shanty Bay

5.0 out of 5 average rating, 34 reviews

Stylish Town For 5, Ravine Backyard, Resort Pool

Oct 21 – 28

G$21,895 GYD per night

Destinations to explore