Holiday houses in Grey Highlands

4.98 out of 5 average rating, 151 reviews

Tiny home in Kimberley

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

4.98 out of 5 average rating, 182 reviews

Barn in Eugenia

Blue Barn Bed n Bale / Blue Mountain

2 q beds. Main bunky bed, 1 bedroom (please inform if second bed is needed) A relaxing, peaceful farm stay on a working farm with or without your horses. Bright clean bunky built in 2016 in our 160 year old barn. The space is new, cozy and offers a chance to spend hours of time with your horses or ours. Nothing like having coffee with the horses.We back on to 30,000 acres of trailed crown land and the Kolapore Trails lending itself to horseback riding, hiking, snow shoeing, mountain biking.

4.87 out of 5 average rating, 351 reviews

Tiny home in Meaford

Tiny Home Nestled between Thornbury & Meaford

Tiny home situation 10 min to Thornbury and 10 min to Meaford, and 20 min from Blue Mountain Village, nestled a country/residential area. 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. INTERNET just upgraded! Window Aircon/pool opens end of May or June.

4.98 out of 5 average rating, 112 reviews

Cottage in Southgate

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.

4.98 out of 5 average rating, 396 reviews

Cabin in Kimberley

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.

4.94 out of 5 average rating, 109 reviews

Home in Badjeros

JJ’s small town country retreat

Take a step back in time to this old farm house. Located on the corner of our little town called Badjeros. This house was built in the 1930s and it’s been in our family for over 80 years. Since then there has been numerous upgrades to the house as well as a large 1200 square foot open concept addition built onto the existing house. While out in the country, this house is central to many attractions in the area 1.5 hours south of Toronto/GTA. Blue Mountain/ Collingwood is 30 minutes north.

4.96 out of 5 average rating, 226 reviews

Guest suite in Kimberley

"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.

4.88 out of 5 average rating, 110 reviews

Loft in Grey Highlands

The Carriage House @ Trillium Shores, Lake Eugenia

Discover this 30 ACRE year round Lake Eugenia retreat offering woodland, parkland, 3 lakefront access points with 2 docks, 2 spring fed ponds, 2000ft of shoreline! ONLY YOU AND YOUR FRIENDS/FAMILY HAVE USE OF THE ENTIRE BUILDING!!! Only 2 hrs north of Toronto! This is an UPPER STOREY LOFT accommodation. Guests MUST BE ABLE TO CLIMB STAIRS! Large upper storey deck with loungers, table, chairs, and BBQ for alfresco dining when the weather permits. Grey Highlands Licence #STA-2021-30-H

4.95 out of 5 average rating, 131 reviews

Chalet in Grey Highlands

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.

4.96 out of 5 average rating, 271 reviews

Tiny home in Arthur

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 fire and gaze at the stars. Enjoy fine dining at the Elora Mill and Spa, enjoy popular shops or hike the Elora Gorge nearby.

Chalet in The Blue Mountains

4.84 out of 5 average rating, 785 reviews

Blue Mountain / Collingwood Hill Side Condo

Ski To Ski From - Studio Condo with a mountain view. 5 minute walk to the north chairlift. Easy keypad check in. Relax in style in this beautiful, newly renovated ground floor unit located at the newly remodeled North Creek Resort at Blue Mountain. Located minutes from the award winning le Scandinave Spa, some of the most scenic golf courses in Ontario, the condo is also located in one of the province's prime destinations for lovers of wine, craft beer and cider.

4.83 out of 5 average rating, 110 reviews

Chalet in Flesherton

The Red House-Oasis in woods with hottub

Clean comfort awaits, with comfy beds (king, double, double bunks), a well equipped kitchen, and wood-burning stove. Hottub and wrap around deck overlooking the woods are perfect for relaxing after hiking the Bruce Trail, paddling or swimming Lake Eugenia, a day at Blue Mountain, cycling the countryside, or playing on the beaches of Georgian Bay. Bonfire pit. Explore 3acres of trails. Nestled in the beautiful Beaver Valley close to dining, bakeries, and markets.

Holiday rentals for every style

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Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Popular amenities for Grey Highlands holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Grey Highlands

5 out of 5 average rating, 10 reviews

Cabin in West Grey

Forest Cabin - Writers Retreat

SeanRating, 5 stars1 week ago

My wife and I stayed here anniversary getaway and were charmed by the space. It felt cozy and isolated and beautifully...simple. It definitely reminded me of the days when I wanted to be writer and have a private getaway, lol. Anastasia gave us the information we needed was lovely to meet.

4.98 out of 5 average rating, 87 reviews

Chalet in Meaford

Sundance of Blantyre Lodge w Hot Tub, Sauna & Pond

SabinaRating, 5 stars2 weeks ago

We thoroughly enjoyed our stay. The place was beautiful and exactly as described. Michelle was a terrific host. I would highly recommend staying here.

4.95 out of 5 average rating, 38 reviews

Cottage in Flesherton

Four Season Waterfront Cottage on Lake Eugenia

SoleRating, 5 stars9 months ago

Our family had a fantastic vacation at Paula and Chris’s cottage on Lake Eugenia. This beautifully rustic and well-loved cottage is perfectly equipped for guests of all ages and interests. Although the weather started off cold and rainy, and not good for swimming at first, we took the opportunity to explore the nearby Bruce Trails, just a short 5-10 minute drive away, where we enjoyed spectacular views. Back at the cottage, the fire pit made our evenings cozy and memorable, and the hot tub was an amazing bonus while we waited for the weather to improve. Once the sun came out, the kids couldn’t wait to jump into the lake, and they had an absolute blast! The Lily pad was amazing- hours and hours of uninterrupted fun. Lake Eugenia is a stunning spot perfect for swimming and just the right size for exploring by canoe or kayak. A big thank you to Chris and Paula for being such wonderful hosts!

4.95 out of 5 average rating, 293 reviews

Dome in Nottawa

One-of-a-Kind Dome Stay near Collingwood!

BrentRating, 5 stars2 weeks ago

While this is strictly speaking a review, let us start by publicly saying a warm Thank You! to Nikki and Joel for creating and sharing such a wonderful space to relax and unwind in! While perhaps lacking in some of the things we take for granted like plumbing, their space is transformative, showing new possibilities, combining beauty and functionality. While on the rustic side, it brings a chance to be more intimate with your surroundings. My wife was particularly in love with the swing chair and hammock right in the space. Highly recommended, very close to Collingwood and all it offers, a great escape.

Cottage in Flesherton

4.89 out of 5 average rating, 9 reviews

Nordic Nook: Family Retreat with Salt Pool

TerryRating, 5 stars10 months ago

Nick’s place was wonderful. Everything was as expected and Kylie (co-host) was quick to respond to messages. The cottage was clean, well organized and has a great layout. We felt right at home. The beds and linens are of good quality. The yard is great and the pool and hot tub were definite highlights. I 100% recommend Nick’s Nordic Nook.

4.86 out of 5 average rating, 21 reviews

Apartment in Collingwood

Cozy cute weekend après-ski

JoyceRating, 5 stars3 days ago

The place was cozy and cute! Good space in the living room and kitchen to hang out with friends and do what is needed. Check in and out was super easy and instructions were very clear. It may be a bit cold but extra blankets were available and Emma did say to reach out if it wasn’t enough, just wear a sweater when walking around. Location was very convenient to Blue Mountain as well. Thank you Emma!

Shipping container in Markdale

5 out of 5 average rating, 3 reviews

Cozy place to lay your head!

MckenzieRating, 5 stars7 months ago

10/10 stay here! Such a cute little cabin on a beautiful property. Definitely a bonus with the animals we saw in the morning!