Vacation rentals in Hillsdale

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Top-rated vacation rentals in Hillsdale

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Guest favorite

Guest suite in Moonstone

4.83 out of 5 average rating, 195 reviews

SKI & RELAX @ our 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.

Guest favorite

Dome in Bradford West Gwillimbury

4.96 out of 5 average rating, 295 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...

Guest favorite

Guest suite in Phelpston

4.96 out of 5 average rating, 202 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(max4)relaxing getaway. 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 Ex Large Driveway Pool is Heated Jun1-Sept30 Surrounded by Ski Resorts, Beaches, Trails and Vetta Nordic Spa. Check in/out time are firm

Guest favorite

Condo in Oro

4.95 out of 5 average rating, 111 reviews

Pet-friendly, 1 BR condo in Horseshoe Valley

All-season Condominium in Horseshoe Valley. Spacious BR with ensuite. Living room with fireplace, dining space, sofa bed. Private balcony, kitchen with all the necessities. Walk to the new Vetta Nordic Spa. Golfing, , driving range across the road, hiking & biking trails, treetop trekking, restaurants, groceries- 5 min drive. Enjoy the onsite amenities- indoor/outdoor pool, hot tub, sauna, gym, , BBQ Barrie , Orillia , Wassaga beach are 20 min. drive( beach #3 is PET FRIENDLY)

Guest favorite

Guest suite in Minesing

4.84 out of 5 average rating, 115 reviews

Farmhouse GUEST SUITE- Pool, hot tub, horses

Unique Farmhouse stay in modern Guest Suite Wrap around porch for a glass of wine or your morning coffee. Spend a lazy day relaxing in the salt water pool and hot tub. Watch the horses graze in the field and catch the breeze from your spot under the barn beam pergola. Toast a few marshmallows over a warm fire and check out the stars in the clear night sky. Horses may not be visible in winter months. Winter: On snowmobile trail close to ski hills, hot tub EVENTS are not permitted.

Guest favorite

Condo in Oro

4.89 out of 5 average rating, 149 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.

Guest favorite

Guesthouse in Shanty Bay

4.99 out of 5 average rating, 135 reviews

The Guest House, Maplewood Hills

The Guest House is set in the midst of our beautiful hardwood forest and is only minutes from Horseshoe Resort and Vetta Spa. Being separated from the main house by a 4 car garage ensures you have full privacy. You will enjoy the full kitchen, dining area and cozy living room. 2 bedrooms & 2 bathrooms provide a comfortable oasis after a day of hiking the trails or skiing & tubing the hills. Prepare your favourite dish on the BBQ and end the day with a hot drink around the campfire.

Guest favorite

Dome in Hawkestone

4.94 out of 5 average rating, 253 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.

Guest favorite

Condo in Oro

4.89 out of 5 average rating, 207 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!

Guest favorite

Cottage in Tiny

4.94 out of 5 average rating, 242 reviews

Bluestone

Bluestone is located less than 10 minutes' drive from beautiful Awenda Provincial Park in Tiny, Ontario. Every choice was made with guest comfort in mind. In the Summertime, take a short walk down a wooded path to Georgian Bay and perfect swimming, or explore a hiking trail and take in the natural beauty of the area. In Winter, enjoy skiing and snowshoeing locally, or stay in, put a record on, and cozy up by the fire. License #STRTT-2024-017

Guest favorite

Cottage in Wasaga Beach

4.95 out of 5 average rating, 260 reviews

GATED RESORT COTTAGE

[CLICK SHOW MORE FOR IMPORTANT INFO] Sought-after cottage located in the gated Wasaga Country Life resort; professionally managed year-round by Parkbridge. A short walk from the beach with full access to resort amenities including; indoor/outdoor swimming pools, private trails, playgrounds, mini golf, sports fields and many more professionally managed facilities. View the "Where you'll be" section below for a full list of amenities.

Guest favorite

Cottage in Tiny

4.95 out of 5 average rating, 221 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.