Vacation rentals in Grey Highlands

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Top-rated vacation rentals in Grey Highlands

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

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Guest favorite
Guest suite in Moonstone
4.86 out of 5 average rating, 310 reviews

RELAX @ our HOT TUB and SAUNA in the woods

PLEASE READ! Mt. St. Louis & Horseshoe Valley at doorstep! This is a bright, large and private walk-out GUEST SUITE (basement apartment). Hot tub, patio, fire pit & secluded path in the woods to enjoy nature. Kitchen is equipped with an induction cooktop and all things necessary, even wine bottle opener:) Open concept living room/kitchen/dining room with TV & Roku. Bedroom is a work of Art: dark, mysterious and romantic! Custom Queen bed made from weathered barn wood salvaged from our property.

Top guest favorite
The exterior of a charming tiny house is showcased, featuring a rustic wooden design and a welcoming deck. Large windows allow for ample natural light, while a pergola extends over part of the deck, creating a shaded area for outdoor relaxation amidst a lush, green landscape.
Tiny home in Kimberley
4.98 out of 5 average rating, 169 reviews

Hand-Crafted Cabin in Stunning Beaver Valley

Lovingly designed and built tiny house in the heart of the beautiful Beaver Valley. 2 Double beds, small kitchenette, rustic deck & living area with a gorgeous outhouse. The property has extensive edible landscapes & greenhouse filled with seedless grapes & edible perennials. Beautiful views of the escarpment, close to the Bruce Trail & Beaver River access point for canoeing and kayaking. Shop at the achingly charming Kimberley General Store. Close to Blue Mountains, Thornbury & Collingwood

Top guest favorite
Farm stay in Kimberley
4.95 out of 5 average rating, 103 reviews

Valley View Farm Retreat ~ Hiking, Skiing, Pets

Enjoy this unique 4 bedroom Farm House as a gorgeous space to gather with family or friends. -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.

Guest favorite
A shared heated pool is surrounded by a spacious lawn, featuring lounge chairs and a gazebo for shade. The pool area is bordered by trees and is nestled in a countryside setting with a view of nearby fields.
Tiny home in Meaford
4.86 out of 5 average rating, 408 reviews

Tiny Home Nestled between Thornbury & Meaford

Tinyhome situated 10 min to Thornbury and Meaford, and 20 min from Blue Mountain Village, nestled a country/residential area so it is quiet and dark at night. Has all the basic comforts including spacious 3 piece bathroom. Close drive to beaches and many hikes and cross country ski trails in the area. It is also a 15 minute drive from Beaver Valley Ski Club and a number of different cideries. Shared heated pool available for the summer months. Window Aircon/pool opens end of May or June.

Top guest favorite
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 favorite
A serene outdoor space features four wooden chairs arranged around a fire pit on lush green grass. Behind, two vibrant autumn trees stand beside a tranquil lake, framed by a white fence and scenic hills in the background.
Guest suite in Kimberley
4.97 out of 5 average rating, 258 reviews

"Wine Down" in Scenic Grey Highlands

Join us at “Wine Down”, our beautiful property located on the highlands of the Beaver River Valley, just minutes away from all that Georgian Bay and the Blue Mountains have to offer. It is a very private 1 acre property with an incredible view of water, escarpment and wildlife. Enjoy more than 1,000 sq. ft. of living space including beds for 5, fully equipped kitchen, dining area, living room with large screen TV and full bathroom. Your hosts live on sight in the main level of the house.

Guest favorite
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, 785 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 favorite
Shipping container in Berkeley
4.92 out of 5 average rating, 104 reviews

Shipping container getaway in small country town

Walnut Grove is a 20-foot shipping container that has been lovingly assembled to showcase the restful, unhurried country life of small town Berkeley. Located two hours north of Toronto, this tiny home has plenty of natural light and all the amenities for a modern glamping experience. An ideal space for couples to unwind and explore the local lakes, rivers, waterfalls, and hiking trails (feel free to borrow our complimentary canoe!). Wi-Fi, fire pit, and free parking are available.

Top guest favorite
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.

Top guest favorite
Guesthouse in Neustadt
4.93 out of 5 average rating, 410 reviews

Bunkie in the Country

Now CLOSED until spring The bunkie has a great view of the sunrise. It's a quiet rural area (please note it is a GRAVEL road). Good for couples, solo adventurers, hunters, someone looking to be outside of town. The bunkie is located approx. 30 feet behind our home. For allergenic reasons and safety of animals, we do not allow pets. May not be suitable for those with mobility issues (small hill & stairs). The bunkie has heat and A/C!

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, 184 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
The Lodge is surrounded by lush greenery and features a wraparound deck with outdoor seating. A gentle stream flows nearby, accentuating the natural landscape. The rustic exterior blends seamlessly with the forested backdrop, providing a peaceful and private retreat.
Chalet in Markdale
4.97 out of 5 average rating, 107 reviews

Grey Highlands Lodge

Our Lodge is perfect for a quiet get away from everyday life, a tranquil patch of greenery nestled in the escarpment of Beaver Valley. If you’re looking for a place to relax and recharge, a place for solitude and restoration, then the Lodge may be just what you need. Enjoy yoga on the side deck, reading in a hammock beside the stream, or exploring the many hikes and nearby amenities just a stones throw away.

Popular amenities for Grey Highlands vacation rentals

When is the best time to visit Grey Highlands?

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Avg. priceﺩ.ﺇ635ﺩ.ﺇ668ﺩ.ﺇ591ﺩ.ﺇ525ﺩ.ﺇ558ﺩ.ﺇ595ﺩ.ﺇ672ﺩ.ﺇ701ﺩ.ﺇ544ﺩ.ﺇ555ﺩ.ﺇ529ﺩ.ﺇ819
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Frequently Asked Questions

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

    Experience the best of Grey Highlands with our loft rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • 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.

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

    Yes! Dive into the perfect getaway at one of over 490 vacation homes with pools in Grey Highlands, available on Airbnb. Make a splash and soak up the sun in style!

  • Do loft rentals in Grey Highlands have free parking?

    Absolutely! We offer over 40 loft rentals with free parking in Grey Highlands. Enjoy a tailored experience with all the comforts you desire.

  • Do cottage rentals in Grey Highlands have wifi?

    Absolutely! We offer over 80 cottage rentals with wifi in Grey Highlands. Enjoy a tailored experience with all the comforts you desire.

  • 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 1,190 vacation rentals in Collingwood, and over 710 vacation rentals in Blue Mountain.

  • Do private suite rentals in Grey Highlands have a kitchen?

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

  • What are the most popular amenities for Private Suite Rentals in Grey Highlands?

    Enhance your stay in our Private Suite Rentals with the most popular amenities: over 10 homes with a kitchen, over 10 homes with air conditioning, over 10 homes with free parking, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do condo rentals in Grey Highlands have air conditioning?

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

  • 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.

Quick stats about vacation rentals in Grey Highlands

  • Total vacation rentals

    Explore 1,240 vacation rentals in Grey Highlands

  • Nightly prices starting at

    Grey Highlands vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 88,110 verified reviews to help you choose

  • Family-friendly vacation rentals

    970 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 500 rentals that welcome pets

  • Vacation rentals with a pool

    480 properties feature pools

  • Rentals with dedicated workspaces

    690 properties have a dedicated workspace

  • Wi-Fi availability

    1,190 of Grey Highlands vacation 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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  5. Grey Highlands