Holiday houses in Hillsdale

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Top-rated holiday rentals in Hillsdale

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Guest favourite
A spacious living area features a comfortable brown sofa positioned near a glass coffee table. Natural light pours in through large windows with blinds, illuminating a dining area with seating for four. A modern kitchen is visible in the background, equipped with sleek appliances.
Guest suite in Moonstone
4.86 out of 5 average rating, 311 reviews

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.

Top Guest favourite
A cozy corner features two checkered chairs positioned near a stone hearth. Natural light filters through a large window, highlighting the textured wall. A small table topped with a potted plant adds a touch of greenery, while the warm surroundings evoke a sense of comfort.
Cottage in Victoria Harbour
4.83 out of 5 average rating, 231 reviews

Serenity, Simplicity and Stone

This is a tiny cottage in a sleepy little hollow that opens onto the Georgian Bay. Inside, each stone was carefully chosen and the woodwork was built, piece by piece, by two craftsmen who are highly skilled and passionate about repurposing. It's an art that will leave you in awe; especially if you're worried about climate crisis. The coat hangers are upcycled 100-year-old railway spikes! If you're looking for luxury you will be disappointed but if you're a minimalist you're going to love it.

Superhost
An outdoor pool area is featured, surrounded by lounge chairs and picnic tables. A large building with expansive glass windows serves as a backdrop, while bright blue umbrellas provide shade. The surrounding greenery enhances the tranquil ambiance of the resort.
Condo in Oro
4.79 out of 5 average rating, 140 reviews

Hillside Haven: Serene Studio Retreat for 4

Escape to the serene Carriage Club Resort Studio! Dive into our inviting swimming pool, gather 'round the firepit, or challenge friends to volleyball. Stay active in our modern gym, then explore nearby skiing and golf. Pamper yourself at Vetta SPA or hit mountain biking and hiking trails. Your cozy studio, with a king-size bed and pull-out sofa, sleeps 4 comfortably. Nestled in rolling hills, just a 15-minute drive from Bass Lake's sandy shores. Discover tranquility with a touch of adventure!

Top Guest favourite
The open-concept living area features a comfortable sofa set against wooden accents and a rustic coffee table. The kitchen is visible in the background, equipped with modern appliances. Large windows allow natural light to fill the space, complementing the warm tones of the wood flooring.
Guesthouse in Barrie
5 out of 5 average rating, 243 reviews

Warnica Coach House

Welcome to the Warnica Coach House! This unique and historic property will not disappoint! Built by George R. Warnica in 1900, this spectacular property was the recipient of the Heritage Barrie award in 2018. The Coach House where you will stay, once housed horses and carriages, has been completely renovated top to bottom in 2023 with the finest touches. We are centrally located with a 30 second drive from the 400, and an 8 minute walk to the waterfront, restaurants, and downtown fun.

Guest favourite
The cabin features a cozy exterior with a textured roof and large windows, surrounded by colorful fall leaves. Outdoor furniture is positioned on the deck, and a hot tub is visible. The setting is enhanced by the backdrop of vibrant autumn foliage.
Cabin in Innisfil
4.94 out of 5 average rating, 167 reviews

Lakefront Cozy Cottage w Hot Tub!

On Lake Simcoe this cozy retreat is just an hour north of Toronto Enjoy the stunning sunrises / views and access to a variety of water activities, while the surrounding area provides ample opportunities for hiking, skiing, other outdoor pursuits with many amenities closely. Down the street from Friday Harbour, LCBO, Starbucks 5 star rating a must & ALL guests to be added to booking. Honey, our golden doodle will greet and visit with you. The cabin is to be left SAME as you found it.

Top Guest favourite
A modern living area features two gray sofas arranged around a textured coffee table on a soft area rug. A vibrant blue accent wall displays a musical design, while a television is mounted on the opposite wall. Bright overhead lighting enhances the spacious feel.
Guest suite in Oro Medonte
4.99 out of 5 average rating, 143 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.

Top Guest favourite
A modern bathroom features a freestanding soaking tub situated next to a window, allowing natural light to fill the space. The vanity displays a mirror and toiletries. Nearby, a spacious bed with soft linens is visible, set against a backdrop of wooden walls.
Place to stay in Wasaga Beach
4.99 out of 5 average rating, 369 reviews

Newly Built Woodsy Retreat - Your Perfect Escape

Woodsy Loft, an ideal home base for not just the beach and stunning sunsets, but Blue Mtn, Scandinave Spa, C-wood, brand new casino, all close by. Many bars, restaurants, beach and other things to do, within 5 min. Great place to stay in, too. Packed with amenities like screened in patio, XL bathtub w/ towel warmer, King size bed, 'The Frame' TV, full kitchen, fast WIFI, motorized blind...and the list goes on. Situated and designed to offer max. privacy and relaxation.

Guest favourite
A bright and spacious living area features a comfortable white sofa paired with dark blue accent chairs. A stylish dining table is set for meals, while a gas fireplace and mounted television create a cozy atmosphere. Natural light fills the room through large windows.
Home in Shanty Bay
4.85 out of 5 average rating, 109 reviews

King Bed, Pool, Gym, Ravine View, Your Getaway!

Enjoy a stylish experience in this spacious and serene space at Highland Estates Resort. You get a completely equipped designer suite that is perfect for couples sneaking away, or families looking for the perfect vacation. Enjoy a peaceful night in your private Jacuzzi then snuggle up in a King Bed. The next day, prepare your own meal in the fully equipped kitchen with Microwave and Electric Stove. Access Netflix, Prime, Disney+. Our Pool is Open! Book Us Today

Guest favourite
A spacious bed is centered in the room, adorned with a decorative throw pillow. Nightstands are positioned on either side, each featuring a lamp that casts a soft glow. Framed artwork enhances the wall above the bed, contributing to a calming atmosphere.
Condo in Oro
4.74 out of 5 average rating, 325 reviews

Cozy Deluxe Studio 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!

Top Guest favourite
A spacious bedroom area features a queen bed adorned with light bedding. A large wall-mounted TV is visible, and a cozy rug lies on the floor. Two comfortable chairs with bright yellow cushions provide seating beside the bed. Natural light streams in through a small window.
Guest suite in Barrie
5 out of 5 average rating, 204 reviews

Private Basement Suite in a family neighborhood

Clean & spacious private Basement suite in a family neighborhood with all amenities that you may require for your stay. Features a queen bed, bathroom and kitchen. Free Parking is included. Highway 400, Park Place, Walmart, Costco, Canadian Tire are within 5-7 minutes driving distance. We offer our guests complete privacy from check-in to check-out, but always available if needed. Perfect for savvy budget travelers who deserve quality stay.

Top Guest favourite
A living room features a flat-screen television mounted on a stone accent wall above a small fireplace. A cozy armchair and a wooden dining table with matching chairs are visible. Natural light filters in through a window adorned with soft curtains.
Condo in Oro
4.95 out of 5 average rating, 176 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. Skiing , golfing , hiking & biking trails, treetop trekking, restaurants, groceries- 5 min drive Barrie , Orillia , Wassaga beach are 20 min. drive( beach #3 is PET FRIENDLY) Please note: we are NOT able to accept cats!

Guest favourite
Cottage in Lafontaine
4.84 out of 5 average rating, 271 reviews

Cozy Beach Cottage with Pool | Georgian Bay

Georgian Bay Beach club. Cute cottage perfect for families, couples, or anyone wanting to relax! 2 bedrooms, 1 bathroom, furnished, pool and private beach on the shores of beautiful Georgian Bay in Tiny township. Cottage is part of a 12 cottage community that shares the pool and beach area. Always super clean, professionally cleaned after every guest! Note: pool is closed October to mid May.

Popular amenities for Hillsdale holiday rentals

  1. Airbnb
  2. Canada
  3. Ontario
  4. Simcoe County
  5. Hillsdale