Vacation rentals in Grey Highlands

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Grey Highlands

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

%{current} / %{total}1 / 1
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, 105 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.

Top guest favorite
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, 155 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.

Superhost
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, 411 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, 260 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, 792 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🌿

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.

Guest favorite
The bedroom features a spacious bed with light blue and white bedding, complemented by decorative pillows. A piece of coastal artwork adorns the wall above the bed. Natural light filters in through the window, illuminating the light-colored walls and wooden ceiling beams.
Apartment in Blue Mountain Resort Area
4.87 out of 5 average rating, 185 reviews

1BR Boutique Suite #7 - The Lake at Blue Mountains

Experience The Comforts of Home While You're Away & we are pet friendly! All rental check-ins are “non contact/digital” and every suite has it’s own heating and cooling system (no shared air)! All our suites are fully contained and separated with concrete walls & outside access only (no shared hallways or doors). Your safety is our priority! Just drive-up and check yourself in safely. Located in a quiet community, we ask that there are no parties or events

Guest favorite
Home in Blue Mountain Resort Area
4.88 out of 5 average rating, 117 reviews

Rivergrass Oasis Across from Blue Mtn Hot Tub!

Rivergrass Oasis is located in the Beautiful Rivergrass community adjacent to Blue Mountain. This unit backs onto Monterra Golf Course, the community swimming pool and hot tub. This unit is within a 5-7 minute walk to the heart of Blue Mountain Village and Monterra Golf Course. Making this property an ideal location for those that want to park their car and walk to the all amenities at Blue Mountain such the ski hills, restaurants, shops, and activities.

Top guest favorite
A rustic bunkie is nestled among lush trees, featuring a wooden porch with steps leading to the entrance. Two outdoor chairs are positioned beside a circular stone fire pit, creating a relaxed atmosphere for gatherings. A variety of greenery surrounds the area.
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, 186 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.

Popular amenities for Grey Highlands vacation rentals

When is the best time to visit Grey Highlands?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$36,194 GYDG$38,077 GYDG$33,684 GYDG$29,918 GYDG$31,801 GYDG$33,893 GYDG$38,287 GYDG$39,960 GYDG$30,964 GYDG$31,592 GYDG$30,127 GYDG$46,655 GYD
Avg. temp-7°C-6°C-1°C6°C12°C17°C20°C19°C15°C9°C3°C-3°C

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 tiny house rentals in Grey Highlands?

    Experience the best of Grey Highlands with our tiny house rentals, starting at about $80 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 1,190 vacation rentals in Collingwood, and over 710 vacation rentals in Blue Mountain.

  • Do cottage rentals in Grey Highlands have air conditioning?

    Absolutely! We offer over 60 cottage 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 cabin rentals in Grey Highlands have wifi?

    Absolutely! We offer over 30 cabin 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 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 G$6,276 GYD 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

  1. Airbnb
  2. Canada
  3. Ontario
  4. Grey County
  5. Grey Highlands