Holiday houses in Grey Highlands

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Top-rated holiday rentals in Grey Highlands

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

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Top Guest favourite
Vibrant autumn foliage displays shades of yellow and orange surrounding a geodesic dome. A pathway of stone steps leads through a lawn covered in colorful leaves, creating a serene outdoor setting amidst lush greenery.
Dome in Bradford West Gwillimbury
4.96 out of 5 average rating, 461 reviews

Four season glamping dome under the stars

Whether you are looking for a romantic getaway for two, a solo remote work week in solitude surrounded by nature, or a family adventure, this 4-season geodesic dome is just the right place. Explore picturesque trails of Scanlon Creek Conservation Area, enjoy inground pool in summer, experience breathtaking sunsets over the farm fields, the starry skies by the bonfire, mesmerizing dance of fireflies in June, and let the frogs and crickets lull you to sleep in the place where time stands still...

Top Guest favourite
Cottage in Kimberley
4.91 out of 5 average rating, 360 reviews

Vintage School House ~Hiking, Family, Pet Friendly

Gather with family or friends in this vintage 5 bedroom School House in the Beaver Valley. -Ideal location to come together, relax, & connect. -Central heat & AC. -Take in the spectacular views of the Beaver Valley. -Explore the Niagara Escarpment and lookouts of the Bruce Trail. -Relax and read by the fireplace. -5 min walk to our swimming pond with dock & beach. -Convenient drive to groceries and local villages. -25 min drive to the Blue Mountains. -Reliable, consistent high speed internet.

Top Guest favourite
A modern cottage features a stone exterior with a sloped roof, harmoniously blending into the surrounding forest. A cozy propane fireplace is visible on the patio, which overlooks a gently flowing stream bordered by smooth stones and lush greenery.
Cottage in Southgate
4.99 out of 5 average rating, 162 reviews

Luxurious Creek Retreat With Hot Tub

Welcome to this luxury cottage on the water. The perfect place to relax and unwind while listening to the waterfall and babbling brook flowing past only a few feet away. If you're looking for privacy and tranquility along with all the pleasures of a luxury stay then look no further. This property boasts a propane fireplace inside as well as one outside, in-floor heat and A/C. Fully equipped kitchen, two bedrooms with hotel quality mattresses and a bathroom that exudes high-end style and decor.

Top Guest favourite
Two glasses of rosé wine sit on a decorative table, capturing sunlight against a backdrop of rolling hills. The landscape features vibrant autumn foliage in shades of orange and yellow, with a clear blue sky and wispy clouds visible above.
Place to stay in Chatsworth
5 out of 5 average rating, 124 reviews

Secluded Cabin overlooking Valley.

Our comfy one-room cabin sits on the edge of 40 wooded acres, overlooking a pastoral valley. Enjoy a relaxing breakfast (included) on the deck while taking in the countryside view, and in the evening, lose yourself in the deep, dark, star-studded sapphire sky. A great home base as you experience the area - hiking beaches, waterfalls, cideries, vineyards and wineries. See more things to do at visitgrey. ca. Or stay put and enjoy your secluded getaway. Read a book, take a hike, or have a nap.

Top Guest favourite
The entrance of a yurt is featured, showcasing a wooden deck with a decorative orange door. The circular structure is surrounded by lush greenery, highlighting the natural setting. Soft light filters through the trees, creating a peaceful outdoor environment.
Yurt in Meaford
4.99 out of 5 average rating, 182 reviews

Quiet Retreat for Two

Spend a starry night in the country with the comfort of a soft bed, a wood stove, and plenty of space both indoors and out. Our yurt is located in a pocket of trees next to rolling farm fields and beautiful conservation land that the Rocklyn creek meanders through. You can prepare your meals in a sweet outdoor kitchen that is entirely screened in- or choose to sit by the fire. Bruce Trail access is just around the corner, and the towns of Meaford and Owen Sound are a short scenic drive away.

Top Guest favourite
A tranquil cabin is nestled among tall trees in a lush forest. A clear path, lined with smooth stones, leads to the cabin's entrance, which features a welcoming front porch. Sunlight filters through the trees, illuminating the natural surroundings.
Cabin in Kimberley
4.98 out of 5 average rating, 411 reviews

Kimberley Creek Cabin

Kimberley Creek Cabin is located in Kimberley, Ontario on a 2 1/2 acre lot surrounded by an old growth forest with a stream running through the property. If you are looking to connect with nature and you enjoy upscale facilities, then this special vacation spot gives you the best of both worlds. Nightly rate includes HST. We are close to hiking, cycling, canoeing, golfing, winter sports, spas, art studios, and fine dining, or simply relax by the firepit or on one of two private decks.

Top Guest favourite
A charming A-frame cabin stands amidst lush green trees, with expansive glass doors opening to a wooden deck. Comfortable seating arrangements are present, complemented by planters filled with blooming flowers, creating a serene and inviting outdoor space.
Place to stay in Southgate
4.99 out of 5 average rating, 280 reviews

Aframe cabin by babbling brook with sauna & hottub

Cabin is partially OFF GRID in winter months (Nov 1-May 7) No running water/shower/indoor bathroom at this time. Water is provided with water dispenser/maintained outhouse Sauna & jacuzzi tub available yr round. Note: Wood hot tub replaced in 2025 with jacuzzi spa Cabin heated by wood stove in the winter months and supplemented with a mini split heater. Firewood/kindling provided Cabin situated on heavily treed 1 acre property with a creek directly in front of a quiet municipal road

Guest favourite
A serene backyard features a glowing hot tub and a cozy fire pit surrounded by colorful chairs. Soft string lights create a warm ambiance against the night sky, highlighting the green lawn and wooden fencing that offers privacy.
Guest suite in Kimberley
4.94 out of 5 average rating, 809 reviews

The Post Office Motel & Spa in the ❤️ of Kimberley

*NEW HOT TUB* Located in the center of Kimberley downtown, a scene straight out of a hallmark movie. Watch the seasons come & go while taking in mtn views and soaking in the hot tub as stars line the night sky.Enjoy marshmallows by the 🔥, amidst this whimsical fortress.Walk to the General Store pick up fresh baked goods and breakfast supplies. Then the dinner choice is yours; Hearts Tavern or Justin’s Oven both just steps away. Bruce trail access at the door. The perfect slow down🌿

Guest favourite
A charming A-frame cabin is surrounded by tall trees, featuring a triangular roof and wooden siding. The entrance includes a white door with a window above, complemented by a small wooden deck with stone accents.
Cabin in Clarksburg
4.96 out of 5 average rating, 123 reviews

Tiny A-Frame near the Bruce Trail

Find yourself nestled among pines trees just steps from the Bruce Trail! This 100 sq. ft. tiny A-Frame offers cozy comfort with two stackable twin beds that convert into a queen (side-by-side) when desired. Amenities include the essentials: BBQ, drinking and dish water, power box to charge devices and a small light, plus an outhouse with a composting toilet. Centrally located near Old Baldy Lookout, Beaver Valley, Blue Mountain and Duncan Caves. The perfect spot to relax and unwind!

Top Guest favourite
A wooden deck connects two buildings, featuring outdoor furniture including two lounge chairs and a blue plastic chair. A picnic table is positioned in front, and a grill can be seen nearby. Lush greenery surrounds the area, providing a calm outdoor environment.
Chalet in Grey Highlands
4.95 out of 5 average rating, 156 reviews

Private 5 Acre Chalet with Bunkie & Sauna

An enchanting, private, 4 season retreat in the escarpment atop Beaver Valley, metres from a beautiful section of the Bruce Trail. The property has nearly 5 acres with cut trails, hammocks, and a sports field. It has two buildings connected by a large deck that has outdoor furniture and a BBQ. The sauna is just feet away. The buildings are fully outfitted offering a comfortable base for daily adventuring, or a stay put retreat. This spot is ideal for a family, or a couple's getaway.

Top Guest favourite
The modern tiny home features a black exterior and a large glass front, allowing natural light to illuminate the interior. A simple outdoor seating area with two chairs is visible, surrounded by lush greenery and trees, creating a connection with the serene natural surroundings.
Tiny home in Arthur
4.97 out of 5 average rating, 370 reviews

Luxury tiny home on peaceful country estate

Escape to Heirloom Tiny Home - where macro luxury meets a micro footprint. Nestled on 23 peaceful acres, surrounded by aspen and pine forests, just 10 minutes from the picturesque town of Elora. Wake up to serene pond views as horses and sheep graze in your view. Organic linens, artisanal soaps, and a spa-like bathroom soothe the senses. Cozy up by the indoor fire and gaze at the stars. Enjoy fine dining at the Elora Mill and Spa, enjoy popular shops or hike the Elora Gorge nearby.

Top Guest favourite
The log cabin is surrounded by vibrant autumn foliage, with a large front deck and stairs leading to the entrance. The natural wood exterior is complemented by a gabled roof. Softly illuminated lanterns are positioned by the door, enhancing the inviting appearance.
Cabin in Flesherton
4.96 out of 5 average rating, 112 reviews

MapleHaven Cabin @ Lake Eugenia

A rustically elegant log cabin sitting on an acre of beautiful mature maple trees on a quiet dead-end street. Find peace and tranquility in the rustic atmosphere the log cabin setting provides, but enjoy all of the comforts of home. Enjoy 3 bedrooms ,2 baths with a master bedroom that features a coffee bar and covered balcony . Located at Lake Eugenia, in the heart of the scenic Beaver Valley, a 4 seasons playground. Walking distance to public beach/boat launch.

Popular amenities for Grey Highlands holiday rentals

When is the best time to visit Grey Highlands?

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Avg. price$296 NZD$312 NZD$276 NZD$245 NZD$260 NZD$278 NZD$314 NZD$327 NZD$254 NZD$259 NZD$247 NZD$382 NZD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Grey Highlands?

    Grey Highlands has more than 970 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cabin rentals in Grey Highlands?

    Experience the best of Grey Highlands with our cabin rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Grey Highlands?

    Four-legged friends are welcome in Grey Highlands. Choose from more than 500 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Grey Highlands?

    Yes! Work meets play with ease at over 690 vacation rentals in Grey Highlands featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Grey Highlands vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 480 vacation homes with pools in Grey Highlands, available on Airbnb. Make a splash and soak up the sun in style!

  • Where should I stay in Grey Highlands?

    Make yourself at home in Grey Highlands by choosing from our most frequently booked neighborhoods. We have over 50 vacation rentals in Markdale, over 1,220 vacation rentals in Collingwood, and over 760 vacation rentals in Blue Mountain.

  • Do private suite rentals in Grey Highlands have air conditioning?

    Absolutely! We offer over 10 private suite rentals with air conditioning in Grey Highlands. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Grey Highlands have a kitchen?

    Absolutely! We offer over 330 condo rentals with a kitchen in Grey Highlands. Enjoy a tailored experience with all the comforts you desire.

  • Do bed and breakfast rentals in Grey Highlands have wifi?

    Absolutely! We offer over 10 bed and breakfast rentals with wifi in Grey Highlands. Enjoy a tailored experience with all the comforts you desire.

  • Do bed and breakfast rentals in Grey Highlands have free parking?

    Absolutely! We offer over 10 bed and breakfast rentals with free parking in Grey Highlands. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Grey Highlands

  • Total holiday rentals

    Explore 1,250 holiday rentals in Grey Highlands

  • Nightly prices starting at

    Grey Highlands holiday rentals start at $69 NZD per night before taxes and fees

  • Verified guest reviews

    Over 92,310 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,000 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 510 rentals that welcome pets

  • Holiday rentals with a pool

    540 properties feature pools

  • Rentals with dedicated workspaces

    700 properties have a dedicated workspace

  • Wi-Fi availability

    1,170 of Grey Highlands holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Grey Highlands rentals

  • 4.8 Average rating

    Grey Highlands stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore

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