House vacation rentals in Grey Highlands

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Quick stats about house rentals in Grey Highlands

  • Total vacation rentals

    Explore 270 vacation rentals in Grey Highlands

  • Nightly prices starting at

    Grey Highlands vacation rentals start at G$8,364 GYD per night before taxes and fees

  • Verified guest reviews

    Over 9,000 verified reviews to help you choose

  • Family-friendly vacation rentals

    240 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 130 rentals that welcome pets

  • Vacation rentals with a pool

    70 properties feature pools

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wi-Fi availability

    270 of Grey Highlands vacation rentals include wi-fi 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!

Top-rated house rentals in Grey Highlands

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

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Guest favorite
The image captures a tranquil hot tub filled with clear water, positioned on a deck overlooking Georgian Bay. A soft sunset casts a warm glow across the sky, and the silhouettes of a gazebo and dock are visible in the background.
Home in Meaford
4.87 out of 5 average rating, 542 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 favorite
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
5.0 out of 5 average rating, 52 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 favorite
Home in Collingwood
4.93 out of 5 average rating, 111 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
Home in Meaford
5.0 out of 5 average rating, 3 reviews

Greystone Lavender Farm-Hot Tub|Pool Table|KoiPond

Experience your own private lavender farm nestled on 95 breathtaking acres in the rolling hills of Meaford ON. Wander fragrant lavender fields, soak beneath the stars in the hot tub, challenge friends to a game of pool, and experience the perfect blend of modern luxury and timeless farmhouse charm. Peaceful, romantic, and unlike anywhere else, this unforgettable retreat is also the perfect setting for intimate weddings, celebrations, family gatherings, and unforgettable countryside escapes.

Top guest favorite
An open game room features a polished wooden pool table at its center, surrounded by exposed timber beams and vibrant green walls. Large windows provide natural light, while a television is mounted nearby. Additional seating is available, enhancing the space's social atmosphere.
Home in Meaford
4.98 out of 5 average rating, 113 reviews

Birdsong, the perfect Blue Mountains getaway

Welcome to Birdsong: a lavishly comfortable, highly unique, year-round space designed with an eye for the eclectic and enjoyable. This enchanting vacation property boasts an enormous hot tub that doubles as a heated indoor pool; as well as a sauna, well-equipped boutique gym, pool table, dedicated conference room/business center, outdoor fire pit and treehouse for kids. Surrounded by the gorgeous Blue Mountains, Birdsong is the perfect ski season rental; as well as summer family getaway.

Top guest favorite
Home in West Grey
4.96 out of 5 average rating, 23 reviews

Woodland River Retreat With Hot Tub

Welcome to this modern, stylish and private cottage escape. Located on the beautiful Saugeen River in the picturesque village of Glenelg Centre, Grey County this cozy cottage offers up private accommodations in a forest setting with sweeping river views. If you're looking for privacy and tranquility along with all the pleasures of a luxury stay then look no further. Fully equipped kitchen, two bedrooms with hotel quality mattresses and a bathroom that exudes high-end style and decor.

Top guest favorite
Home in Meaford
4.98 out of 5 average rating, 109 reviews

Stonefox Retreat: Acerage, Pond, Hot Tub & Sauna

This stunning century home has been family-owned for over 50 years. A limestone cottage built in 1850 with a modern addition this is a huge house on an entirely secluded acarage with a lake-sized swimming pond with floaties and a dock. A true escape through time, but with modern amenities, this property is loved by all ages. There is ample room to gather and to retreat. It's a perfect choice for families and / or groups of friends to get together in their own private world.

Guest favorite
Home in Collingwood
4.92 out of 5 average rating, 114 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.

Superhost
A hot tub is set under wooden beams, providing a calming retreat. It overlooks a grassy area leading to the waterfront, where bright red Muskoka chairs are positioned. Steps lead up to the deck, enhancing outdoor accessibility and views.
Home in Victoria Harbour
4.87 out of 5 average rating, 107 reviews

Modern Waterfront Home on Georgian Bay w/ Hot Tub!

Escape to a peaceful haven with this new and breathtaking modern waterfront cottage. Immerse yourself in the stunning views from the walkout deck with outdoor seating, a hot tub and a BBQ area. Quiet neighbourhood in Victoria Harbour on Georgian Bay. Short drive to charming town of Midland and nearby attractions such as the Tay Shore Trail and the Wye Marsh Wildlife Centre. This bright and beautifully finished home is less than a 2-hour drive from the GTA.

Top guest favorite
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, 46 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 favorite
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, 210 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 favorite
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
5.0 out of 5 average rating, 21 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

Popular amenities for Grey Highlands house rentals

When is the best time to visit Grey Highlands?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$53,529 GYDG$48,720 GYDG$45,374 GYDG$37,219 GYDG$43,701 GYDG$44,120 GYDG$49,765 GYDG$53,111 GYDG$47,047 GYDG$44,747 GYDG$44,329 GYDG$57,502 GYD
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Destinations to explore