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House holiday rentals in Grey Highlands

Find and book unique houses on Airbnb

Top-rated house rentals in Grey Highlands

Guests agree: these houses are highly rated for location, cleanliness and more.

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Guest favourite
Home in Meaford
4.87 out of 5 average rating, 530 reviews

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

Guest favourite
A spacious dining area features a large wooden table set for eight, surrounded by black chairs. A modern chandelier hangs above, illuminating the setting. Large windows offer views of the outdoors, allowing natural light to fill the space.
Home in Kimberley
5 out of 5 average rating, 48 reviews

Beaver Valley Vista: Secluded w Hot Tub, Fire Pit

Welcome to Valley View Cottage! Nestled in the heart of nature, this retreat offers a picturesque escape. With four cozy bedrooms, relaxing hot tub, and a mesmerizing fire pit, it's the perfect getaway. Immerse yourself in the beauty of the valley, explore nearby hiking trails, or simply unwind in the comfort of our rustic yet modern cottage. ✔ 4 Comfy Bedrooms ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Fire Pit, Balcony, Hot Tub ✔ Pool table, dart board, ping pong table Learn more below!

Top guest favourite
Home in Collingwood
4.93 out of 5 average rating, 108 reviews

The Artist's House B&B: Relax, Explore Collingwood

Welcome to The Artist's House — a charming getaway in the village of Nottawa, just minutes from Blue Mountain, Collingwood, Scandinave Spa, and Georgian Bay beaches. 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. Relax on the patio, enjoy the BBQ and fire pit, and experience the perfect blend of village charm and nearby adventure. Fast Wi-Fi & parking.

Superhost
A charming lodge is surrounded by lush trees, featuring gray wooden siding and a stone pathway leading to the entrance. The structure includes a distinct chimney and a small utility shed beside it, creating a cozy, inviting outdoor setting.
Home in Singhampton
4.89 out of 5 average rating, 55 reviews

Blue Mountain Riverside Lodge | Hottub & Sauna

Escape to tranquility at this charming 1-bedroom lodge located in Feversham, just 19 mins from Blue Mountain, 5 mins from Kolapore Trail, and a 2 mins from the general store. Immerse yourself in nature's beauty from the comfort of your private hot tub or unwind in the sauna overlooking the beautiful Beaver River. Whether you're seeking a romantic weekend or a solo retreat, this serene haven promises a perfect blend of comfort and natural beauty. Book now to guarantee the peace that awaits you.

Top guest favourite
A cozy living area features a plush gray sofa and two bright armchairs, inviting relaxation. Natural light filters through the large windows, illuminating the wooden log walls and earthy decor elements, while a small coffee table sits in the center.
Home in Elora-Salem
4.98 out of 5 average rating, 261 reviews

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

Superhost
Home in St. Jacobs
4.89 out of 5 average rating, 103 reviews

Boho 3-Bed House Retreat: HotTub, Sauna Oasis &Spa

Experience luxury in this tranquil full house in Saint Jacobs village, set on a fully fenced acre lot for privacy. It features three bedrooms: 1 king, 1queen, and a child’s bed, plus a home office. The house includes two living rooms, two full bathrooms, and a well-equipped kitchen. Highlight is the retreat oasis with a hot tub, sauna, and outdoor shower. Enjoy spa-like bathrooms with rain showers and a private outdoor patio. Nearby dining and entertainment enhance your rejuvenating getaway!

Guest favourite
Home in Collingwood
4.92 out of 5 average rating, 111 reviews

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.

Guest favourite
A bright living area features a cozy corner seating with natural light filtering through large windows. A simple round coffee table sits centrally on a textured area rug, while a record player is positioned nearby on a cart, enhancing a minimalist aesthetic.
Home in South Bruce Peninsula
4.95 out of 5 average rating, 107 reviews

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.

Top guest favourite
The kitchen features modern cabinetry with blue and white accents. A marble countertop stretches across the kitchen island, which is complemented by a vibrant orange refrigerator. A dining area with a glass table and colorful stools offers a cheerful space for meals.
Home in Flesherton
4.98 out of 5 average rating, 41 reviews

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

Top guest favourite
A modern living space showcases a comfortable gray sectional sofa with colorful accent pillows. A small black table sits in front, complemented by a light area rug. The room is brightened by natural light flowing through two windows, enhancing the inviting atmosphere.
Home in Collingwood
4.95 out of 5 average rating, 203 reviews

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.

Top guest favourite
A charming two-story structure is set amidst lush greenery, featuring a wooden deck that extends from the upper level. Large windows provide natural light, while the building's rustic exterior blends harmoniously with the surrounding landscape.
Home in Meaford
5 out of 5 average rating, 19 reviews

Hilltop Mesa- carriage house on acreage

Peaceful country escape, 20 minutes to Thornbury and Owen Sound. Just two hours from Toronto, a carriage house on 50+ acres of forest and fields of wild flowers. This space offers tranquility, calm, and a place to gather with family or friends. You'll enjoy: - 2 self-contained units (kitchen and bathroom in each) - Outdoor fire pit, patio, balcony - Hiking/walking trails - Incredible sunrise and sunset views

Guest favourite
The kitchen features an open layout with warm wood flooring and a large dining table set for twelve. Natural light enters through two windows beside the door. Stainless steel appliances and a well-equipped countertop complete the functional space.
Home in Kimberley
4.88 out of 5 average rating, 209 reviews

Heart of Kimberley - with views and a hot tub

Welcome to the hamlet of Kimberley nestled in the Beaver Valley. Surrounded by nature, the Rock House is a historic six bedroom century home with beautiful views close to many outdoor activities, and located beside an unassuming gourmet restaurant and a general store with fresh coffee and in-house sourdough bread. We are located 25 minutes from Blue Mountain and 2 minutes from Beaver Valley Ski Club.

Popular amenities for house rentals in Grey Highlands

When is the best time to visit Grey Highlands?

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Avg. price$331 SGD$301 SGD$281 SGD$230 SGD$270 SGD$273 SGD$308 SGD$329 SGD$291 SGD$277 SGD$274 SGD$356 SGD
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Quick stats about house rentals in Grey Highlands

  • Total holiday rentals

    Explore 280 holiday rentals in Grey Highlands

  • Nightly prices starting at

    Grey Highlands holiday rentals start at $65 SGD per night before taxes and fees

  • Verified guest reviews

    Over 8,700 verified reviews to help you choose

  • Family-friendly holiday rentals

    250 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 130 rentals that welcome pets

  • Holiday rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wifi availability

    280 of Grey Highlands holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Grey Highlands rentals

  • 4.9 Average rating

    Grey Highlands stays are highly rated by guests – averaging 4.9 out of 5!

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