Vacation rentals in Grey Highlands

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Top-rated vacation rentals in Grey Highlands

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Guest favorite

Guest suite in Kimberley

4.93 out of 5 average rating, 540 reviews

The Post Office Motel & Spa in the ❤️ of Kimberley

One-of-a-kind relaxation escape located in the charming village of Kimberley! Just 1.5hrs North of Toronto, 20 min to Blue Mtn skiing, mtn top skating and the Village. The Kimberley downtown is something from the movies. Imagine getting out of your car and walking straight into the scene of a warm and cozy snow globe. You can watch the seasons come & go while taking in the valley views. Head outside to enjoy marshmallows by the fire, amidst this whimsical fortress. Bruce Trail access @ the door

Apr 3 – 10

G$33,460 GYD per night

Guest favorite

Barn in Eugenia

4.98 out of 5 average rating, 165 reviews

Blue Barn Bed n Bale / Blue Mountain

2 q. beds A relaxing farm stay on a working farm with or without your horses. Bright clean bunkie 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 your horses in the morning. We back on to 30,000 acres of trailed crown land and the Kolapore Trails lending itself to horseback riding, hiking, snow shoeing, atving, mountain biking. Check out the beautiful sunset behind the barn.

Jan 17 – 24

G$34,905 GYD per night

Guest favorite

Tiny home in Kimberley

4.98 out of 5 average rating, 123 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

Dec 26 – Jan 2

G$26,041 GYD per night

Guest favorite

Chalet in Priceville

4.91 out of 5 average rating, 448 reviews

ReLive Hilltop Chalet w/brand-new hottub, sunrises

Relive Retreat's Hilltop Chalet is a 700 sq ft open concept rustic cabin w/high ceilings, full-length windows, spring water, private + new hot tub, fireplace, BBQ, wrap around deck w/views, hiking trails + more. Perfect for couples, friends or families looking to relax & rejuvenate in nature. If peace is what you are looking for this is it! Occassionally dog friendly so please inquire first. This is a private 72 acre retreat. We live here with our 2 dogs, currently hosting 2 yurts and 2 cabins.

Aug 21 – 28

G$33,689 GYD per night

Guest favorite

Cabin in Kimberley

4.99 out of 5 average rating, 357 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.

Apr 11 – 18

G$39,413 GYD per night

Guest favorite

Guest suite in Kimberley

4.96 out of 5 average rating, 177 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.

Jul 13 – 20

G$15,467 GYD per night

Guest favorite

Chalet in Grey Highlands

4.94 out of 5 average rating, 106 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.

Jul 4 – 11

G$26,066 GYD per night

Superhost

Tiny home in Meaford

4.85 out of 5 average rating, 255 reviews

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 pool available for the summer months with possibilities of covid restrictions. INTERNET just upgraded!

Oct 28 – Nov 4

G$20,924 GYD per night

Guest favorite

Guesthouse in Neustadt

4.92 out of 5 average rating, 302 reviews

Bunkie in the Country

Now Open! 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. We have 2 large dogs on site (live in the house). For allergenic reasons and safety of other 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!

Sep 24 – Oct 1

G$11,294 GYD per night

Guest favorite

Guest suite in Holland Centre

4.97 out of 5 average rating, 193 reviews

Dragonfly Hollow bnb

Nature lovers, Come experience the natural beauty of the Grey-Bruce region. Our home is in a very quite natural setting surrounded by trees. In summer explore the many lakes, beach or waterfalls . Hike the Bruce trail, or one of many others; good for ATVing, Scenic Motorcycle Routes. Fall is especially beautiful, the hills and valleys fill with vibrant colours. In winter, enjoy cross-country, downhill skiing, snowboarding, skidooing. Blue Mountain only a Scenic 40 mins away.

Jan 16 – 23

G$17,360 GYD per night

Guest favorite

Apartment in Meaford

4.98 out of 5 average rating, 293 reviews

Fuller House Airbnb

Steps from Georgian Bay and beach. This newly renovated 400 sq/ft walk out, self-contained apartment is located on a quiet double lot, offering privacy and a beautiful natural setting. Enjoy the comfort of a substantial continental breakfast, homemade baking and more in your cozy kitchenette, or outdoor seating areas. Apartment includes microwave, coffee maker, toaster, kettle and kitchenware. BBQ provided on site. Front of home is owners' living space and Art Studio/Gallery.

May 1 – 8

G$14,716 GYD per night

Guest favorite

Farm stay in Markdale

4.99 out of 5 average rating, 124 reviews

Experience Country Living at Firefly Ridge

Your private living space is comfortable and bright, with lots of picturesque windows and high ceilings. There is a walkout to a private area where you can relax, and unwind, enjoying the sounds of nature and some farm animals, such as horses, minis, donkeys, goats, chickens, cats, 2 Australian cattle dogs and even some piggies. We love our animals and we welcome yours as we are a pet friendly farm. Please note DOGS MUST be on a leash when on the property.

Dec 3 – 10

G$29,760 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Grey Highlands vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Grey Highlands's top sights

Blue Mountain Village319 locals recommend

Scandinave Spa Blue Mountain288 locals recommend

Scenic Caves Nature Adventures258 locals recommend

Living Water Resort & Spa4 locals recommend

Craigleith Provincial Park45 locals recommend

Blue Mountain Resorts Ltd10 locals recommend

Other great vacation rentals in Grey Highlands

Guest favorite

Condo in Collingwood

4.94 out of 5 average rating, 586 reviews

Modern & Chic Sanctuary Suite in Collingwood

Sep 29 – Oct 6

G$24,099 GYD per night

Guest favorite

Place to stay in Wasaga Beach

5.0 out of 5 average rating, 190 reviews

Newly Built Woodsy Loft Retreat

Dec 27 – Jan 3

G$32,885 GYD per night

Superhost

Home in Markdale

4.88 out of 5 average rating, 34 reviews

The Nest in Markdale

Feb 15 – 22

G$17,665 GYD per night

Guest favorite

Cabin in Clarksburg

5.0 out of 5 average rating, 38 reviews

Tiny A-Frame near the Bruce Trail

Sep 5 – 12

G$12,586 GYD per night

Guest favorite

Chalet in Markdale

5.0 out of 5 average rating, 56 reviews

Grey Highlands Lodge

Nov 23 – 30

G$35,915 GYD per night

Guest favorite

Guest suite in Flesherton

4.97 out of 5 average rating, 30 reviews

Aunty Fancy’s Charming Suite in Eugenia

Jan 6 – 13

G$18,791 GYD per night

Guest favorite

Cabin in Kimberley

5.0 out of 5 average rating, 18 reviews

My Creekside Cabin

May 23 – 30

G$38,963 GYD per night

Guest favorite

Bungalow in Grey Highlands

4.97 out of 5 average rating, 89 reviews

The Highlands- 7 Acres Overlooking Lake Eugenia

Oct 23 – 30

G$49,069 GYD per night

Show all

Quick stats about vacation rentals in Grey Highlands

Total rentals
1.4K properties
Rentals with dedicated workspaces
690 properties have a dedicated workspace
Rentals with a pool
440 properties have a pool
Pet-friendly rentals
540 properties allow pets
Family-friendly rentals
1.1K properties are a good fit for families
Total number of reviews
72K reviews

Frequently Asked Questions

How much does it cost to stay in bungalow rentals in Grey Highlands?
Experience the best of Grey Highlands with our bungalow 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 1,060 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 440 vacation homes with pools in Grey Highlands, available on Airbnb. Make a splash and soak up the sun in style!
Do farmstay rentals in Grey Highlands have free parking?
Absolutely! We offer over 10 farmstay rentals with free parking in Grey Highlands. Enjoy a tailored experience with all the comforts you desire.
Do private suite rentals in Grey Highlands have wifi?
Absolutely! We offer over 30 private suite 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 770 vacation rentals in Blue Mountain, and over 10 vacation rentals in Flesherton.
Do guesthouse rentals in Grey Highlands have a kitchen?
Absolutely! We offer over 10 guesthouse rentals with a kitchen in Grey Highlands. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Grey Highlands?
Enhance your stay in our House Rentals with the most popular amenities: over 280 homes with wifi, over 270 homes with a kitchen, over 280 homes with free parking, over 240 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do apartment rentals in Grey Highlands have air conditioning?
Absolutely! We offer over 80 apartment 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 540 vacation rentals for guests traveling with pets.

Vacation rentals in Grey Highlands

Top-rated vacation rentals in Grey Highlands

Vacation rentals for every style

Apartments

Chalets

Cabins

Popular amenities for Grey Highlands vacation rentals

Stay near Grey Highlands's top sights

Other great vacation rentals in Grey Highlands

Condo in Collingwood

Place to stay in Wasaga Beach

Home in Markdale

Cabin in Clarksburg

Chalet in Markdale

Guest suite in Flesherton

Cabin in Kimberley

Bungalow in Grey Highlands

Quick stats about vacation rentals in Grey Highlands

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

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

Are there family-friendly vacation rentals in Grey Highlands?

Are there Grey Highlands vacation rentals on Airbnb with pools?

Do farmstay rentals in Grey Highlands have free parking?

Do private suite rentals in Grey Highlands have wifi?

Where should I stay in Grey Highlands?

Do guesthouse rentals in Grey Highlands have a kitchen?

What are the most popular amenities for House Rentals in Grey Highlands?

Do apartment rentals in Grey Highlands have air conditioning?

Are there pet-friendly vacation rentals in Grey Highlands?

Destinations to explore