House vacation rentals in Grey Highlands

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Quick stats about house rentals in Grey Highlands

  • Total vacation rentals

    Explore 280 vacation rentals in Grey Highlands

  • Nightly prices starting at

    Grey Highlands vacation rentals start at G$10,460 GYD per night before taxes and fees

  • Verified guest reviews

    Over 8,700 verified reviews to help you choose

  • Family-friendly vacation rentals

    250 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

    280 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
Home in Meaford
4.87 out of 5 average rating, 532 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

Top guest favorite
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
4.86 out of 5 average rating, 56 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 favorite
An open and airy space features a large harvest table with pink legs, complemented by wooden chairs. A cozy bench is positioned alongside the table. A staircase leads to a loft area, while art supplies and decor are visible throughout the room.
Home in Desboro
4.97 out of 5 average rating, 139 reviews

Forest Loft - Forest, Sauna, Ponds & Stargazing

The “Forest Loft” is a one-of-a-kind space surrounded by the old-growth trees of Kinghurst Forest. The 1,600-square-foot space sleeps up to four and features two Queen-size beds and linens, huge harvest table, indoor kitchenette with a stovetop and fridge, filtered water, shower, propane and wood stove heating, in-door basketball hoop, hammock, picnic table, a commercial grade BBQ, fire ring and access to two beautiful spring-fed ponds. Access to Finnish sauna for four is available on request.

Guest favorite
A brick exterior with charming white trim leads to a welcoming front door, framed by blooming foliage. A wooden barrel planter fills with vibrant flowers, while a woven chair sits nearby. Decorative string lights add a touch of warmth to the entrance.
Home in Kimberley
4.91 out of 5 average rating, 66 reviews

Charming Kimberley~Kimbuktu Guest House & Retreat

Welcome to Kimbuktu, a perfect place for every occasion. This turn of the century home is located in the charming village of Kimberley, nestled in the magnificent landscape of the Beaver Valley. Newly renovated spacious semi detached unit, comfortable inside with an outdoor adventure paradise right outside your door: rivers, lakes and the famous Bruce Trail. Steps away from the Kimberley General Store & Justin’s Oven. A place of breathtaking natural beauty, home to many artists and studios.

Top guest favorite
Home in West Grey
5 out of 5 average rating, 18 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.

Guest favorite
Adirondack chairs in vibrant colors are positioned on a wooden deck overlooking a tranquil lake. A small table sits between the chairs, and the surrounding area features lush grass and gentle reeds. A distant dock is visible, enhancing the lakeside experience.
Home in Flesherton
4.87 out of 5 average rating, 15 reviews

The Hidden Haven Cottage

Relax, have fun and make memories with the whole family, pups included, at this peaceful lakefront cottage. The cottage, located on Eugenia Lake, boasts floor-to-ceiling windows, a fully equipped kitchen, four bedrooms with luxury linens, cozy fireplaces, and an assortment of outdoor activities, including a dock, firepit, hammock, paddleboards, kayaks, and a canoe. With numerous conservation areas and Bruce Trail access points in the vicinity, there's truly something for everyone.

Top guest favorite
Home in Meaford
4.99 out of 5 average rating, 105 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
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, 108 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 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, 42 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, 204 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 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

Popular amenities for Grey Highlands house rentals

When is the best time to visit Grey Highlands?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$53,555 GYDG$48,744 GYDG$45,397 GYDG$37,238 GYDG$43,723 GYDG$44,141 GYDG$49,790 GYDG$53,137 GYDG$47,070 GYDG$44,769 GYDG$44,351 GYDG$57,530 GYD
Avg. temp-7°C-6°C-1°C6°C12°C17°C20°C19°C15°C9°C3°C-3°C

Destinations to explore

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