House holiday rentals in Grey Highlands

Beach House Hideaway by Post Office Motel *HOT TUB

This beach house was designed with relaxation and the enjoyment of togetherness in mind. Let your worries melt away as you slip into the warmth of this water side hot tub featuring stunning view across Georgian Bay and up the mountain side, as fresh snow falls around you. The open concept design makes this the perfect place to gather with family and friends w/ walkout waterfront patio and dock access for swimming. 2 min to downtown Meaford, 20 min to Blue Mtn, 1.5 hrs to Tobermory. Hiking Trails

Butchart Estate: Breathtaking Victorian mansion

Give them a holiday to remember.  Gather family or friends and settle in to our beautiful and well-equipped heritage home for a few days.  Enjoy the gourmet kitchen, relax in your private indoor pool & hot tub, curl up by the fireplace, binge some Netflix, or play board games galore.  Outdoors, we're famous for our hills, forests, lakes and rivers, the Bruce Trail, and the views out to Georgian Bay.  But don't miss the music, museums, the markets, and amazing foodie scene, steps from your door. 

Log Cabin in the heart of downtown Elora

The Cabin Elora is a beautiful rustic log cabin stylishly updated with modern and hand made furniture from a local artisan. You will enjoy a clean, bright and open concept space. Located in the heart of Elora, walking out the door into downtown yet nestled off the street giving you wonderful privacy and a quiet peaceful atmosphere. Features: • King size bed with Egyptian cotton sheets • Private patio overlooking Metcalfe St. and gardens • Clean, stocked kitchen • Perfect downtown location

The Artist's House B&B: Art, Gardens & Relaxation

Welcome to The Artist's House — a charming, relaxing getaway on 1.5 private acres just outside Collingwood. Surrounded by beautiful gardens, sculpture, and original artwork, our home offers three serene bedrooms, air conditioning, a fully equipped kitchen, and a cozy living room with gas fireplace. Enjoy the patio, BBQ, and fire pit. Experience village charm while being just minutes from Blue Mountain, Scandinave Spa, trails, golf, Collingwood, and Georgian Bay beaches. Fast Wi-Fi included.

Stylish 1870s Home near Distillery District & Old Toronto

Visiting for fifa? Stop here...Steps from the Distillery District downtown, this Top rated listing is a beautifully restored 1870s row-house (townhouse) that blends historic charm with modern refinement. Thoughtfully designed throughout, it’s located downtown also close to St. Lawrence Market, and some of the city’s best cafés and restaurants. In the evening, unwind in the serene, charcoal-toned bedroom beneath the warm glow of a statement chandelier—your refined Toronto retreat awaits

Kiss & Bond Water View Colpoys Bay 4 -Seasons

Hello,, I'm the owner of a newly built home, that I hope I will provide first-rate, memorable experiences for my guests, I'm a nurse for over 30 years, and I love to explore. Im an animals lover, I'm also a mother of 3 boys and have been married for 33 years ,being outdoors is one of my favourite activities, snowmobiling, hiking. I've owned our cottage for 10 years and we decided to rebuild , to enjoy the beautiful views of Colpoys Bay and in the back yard the Bruce Pennisula escarpment .

Quiet Vaughan Retreat near Wonderland & Hwy 400

Enjoy a stylish and peaceful stay at this centrally located one-bedroom lower-level unit, perfect for both leisure and business travelers. With your private entrance, parking, and all the essentials, it’s your ideal home away from home. Features include a full kitchen, bathroom, internet, smart TV, one Queen and one sofa bed, and a functional workspace. Steps from FreshCo, Walmart, restaurants, and services. Minutes to Vaughan Mills, Canada’s Wonderland, Cortellucci Hospital and transit.

JJ’s small town country retreat

Take a step back in time to this old farm house. Located on the corner of our little town called Badjeros. This house was built in the 1930s and it’s been in our family for over 80 years. Since then there has been numerous upgrades to the house as well as a large 1200 square foot open concept addition built onto the existing house. While out in the country, this house is central to many attractions in the area 1.5 hours south of Toronto/GTA. Blue Mountain/ Collingwood is 30 minutes north.

Cozy Collingwood Farm Retreat

Welcome to this very private 2 bedroom home located on a fenced-in 10 acre property that is located just 3 minutes to downtown Collingwood, and 10 minutes to Blue Mountain. Come and relax here after a day on the slopes or hiking trails , and enjoy the warmly decorated living room with a wood stove! Perfect property all to yourself to enjoy ultimate privacy while still being in town and close to everything! Bring the pooch and enjoy everything this property has to offer.

Pine Villa-Mediterranean Cottage with Hot Tub

Escape to our charming Mediterranean-inspired villa nestled in the serene countryside of Ontario. With minimalist aesthetics, the cottage offers a tranquil retreat for relaxation. Immerse yourself in the natural beauty that surrounds as you unwind on the patio or in the hot tub, or explore the countryside with our complimentary bikes. Inside, enjoy minimalist design, cozy details, and a nostalgic record player—where modern comfort meets rustic charm.

Renovated 3-BR Home Near Old Baldy | BBQ & Hot Tub

Newly renovated chalet near Collingwood, Blue Mountain, and Eugenia Lake on a quiet paved road 🚴. Whether you love recreational activities, bird watching, relaxing in a hot tub, or cozying up by a wood-burning fire, this is a perfect place to be inspired by nature and unwind. Near by: - Beaver Valley Ski club - Hearts Tavern - Eugenia Lake - Old Baldy - Kolapore Trails - Metcalf Rock - Collingwood - Blue Mountains - Thornbury - The Roost Winery

100% Private 1-Bdrm+Fireplace. Quiet+comfortable.

Welcome to our fully licensed, renovated unit, nestled on a quiet, residential street. This bright, 100% PRIVATE basement unit offers the perfect blend of comfort and convenience. Stylishly decorated, it combines contemporary style with warm home comforts. Expect a tranquil haven where you can relax and unwind, but still remain close to the action. We're a 5-minute drive to downtown & a 10-minute drive to Blue Mountain.