Holiday houses in Hillsdale

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Top-rated holiday rentals in Hillsdale

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Guest favourite
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.

Guest favourite
A modern kitchen features natural wood cabinetry and a large marble countertop island with seating. Stainless steel appliances, including an electric stove and refrigerator, are visible. The space is well-lit with recessed lighting, and decorative plants add a touch of warmth.
Apartment in Midland
4.9 out of 5 average rating, 129 reviews

Loft By The Bay

Welcome to our charming second storey apartment in downtown Midland, Ontario. This cozy space features a bedroom, office with futon, full kitchen, bathroom, laundry, and a bright open concept living area. Enjoy easy access to local shops, restaurants, and attractions. Explore the picturesque waterfront and nearby hiking trails. Retreat to this comfortable and inviting apartment after a day of work or play. Book your stay today for a convenient, comfortable, and memorable experience in Midland.

Superhost
A spacious living and dining area is presented, featuring a modern dining table set with plates and cutlery. A large sectional sofa faces a wall-mounted TV, with ample natural light filtering through sliding glass doors that open to a deck overlooking the outdoors.
Bungalow in Orillia
4.89 out of 5 average rating, 110 reviews

Charming Main Floor w Hot Tub

Welcome to our charming main floor apartment in the beautiful city of Orillia! This space is is suitable for families or small groups looking for a comfortable stay in a convenient location. This is a fully furnished home that features three bedrooms, one bathroom, a fully equipped kitchen with all the essentials needed to prepare your own meals. The living room is bright and cozy with a 43" Samsung Smart TV including Netflix, unlimited high speed internet and a spacious 6 seater dining table.

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.

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.

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.

Superhost
The spacious living area features a comfortable couch and an additional patterned armchair. Two side tables with lamps are present, providing soft lighting. Large windows with sheer curtains allow natural light to fill the room, while a flat-screen TV is mounted on the wall.
Apartment in Shanty Bay
4.84 out of 5 average rating, 108 reviews

Spacious Hideaway in Nature

Welcome to the charming Shanty Bay area! Embrace the relaxed vibes surrounded by natural beauty. Enjoy leisurely walks by Lake Simcoe or explore nearby parks like Oro-Medonte Rail Trail. Discover local shops and eateries, or indulge in water activities and outdoor adventures. Our cozy Airbnb accommodates 4 guests, with a king-size bed and comfy couches. Experience the best of both worlds - a laid-back getaway and exciting local attractions.

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