Holiday houses in Grey County

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Top-rated holiday rentals in Grey County

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Top Guest favourite
Apartment in Owen Sound
4.97 out of 5 average rating, 103 reviews

Private with Self Check-in Bright & Modern Comfort

License: STR2025-9250261010 Welcome to our bright and clean one-bedroom suite ideal for singles, couples, or small families. Walking distance to the Bruce Trail, a short drive to parks, beaches, and lakes; and a good home base to explore the Bruce Peninsula and Tobermory. A comfortable queen size bed in the bedroom with a selection of bedding and pillows. Fully equipped kitchen, modern bathroom, full suite of TV streaming with high-speed internet. Residential area on the west side of town.

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, 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.

Top Guest favourite
A cozy seating area is featured with a spacious gray sectional sofa adorned with decorative pillows. A coffee table sits in front, with magazines and a remote casually placed on it. A lamp and a window provide soft lighting, enhancing the comfortable space.
Loft in Neustadt
4.97 out of 5 average rating, 172 reviews

Cozy Loft at Carrick Creek Farmstead

Carrick Creek Farmstead is a sanctuary in the corner of Southeast Bruce County in Ontario. The Farmstead offers you 170 acres of rolling hills, a woodlot and walking trails. The Loft is a suite above our garage. A king bed and pull out sofa bed allow accommodation for 4 adults. The loft has kitchen facilities, shower, television, and air conditioning for the summer. Enjoy a meal on the nearby patio. If you would like to enjoy some prepared food from the Carrick Creek kitchen, just ask.

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, 409 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 favourite
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 favourite
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 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.

Guest favourite
Home in The Blue Mountains
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 favourite
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 favourite
A cordwood cabin is surrounded by lush forest, featuring a green living roof. The rustic structure has a wooden door and multiple windows, with a small outdoor seating area that includes two chairs and a table. Stacked firewood is nearby.
Cabin in Chatsworth
4.99 out of 5 average rating, 145 reviews

Peaceful cabin-in-the-woods 50 acre private forest

Relax in a charming cordwood cabin on an off-grid property powered entirely by solar energy. Enjoy exclusive use of 50 acres of varied woodlands with over 4km marked & maintained nature trails (loaner snowshoes provided!) and special features like a SoundForest, a meditative walking labyrinth, plus a sauna made of local cedar... it’s like having your own private park! There’s even an option ($) to have a breakfast basket brought out.

Top Guest favourite
A private balcony is presented with two comfortable chairs adorned with colorful cushions, offering a serene view of lush greenery. The wooden structure features a rustic finish, enhancing the outdoor space for relaxation or quiet moments.
Apartment in Meaford
4.96 out of 5 average rating, 137 reviews

"Paddle" at Hills | Scenic Escape Near Blue Mtn

Welcome to Hills! Once known as Hill's Dairy in Meaford, this historic building has been converted into four rental units with an adventure shop. Steps to downtown Meaford, and minutes to Georgian Bay, Georgian Trail cycling route, the infamous Trout Hollow Trail, shops and restaurants, beaches, and 25 mins from Blue Mountain. This modern suite is the perfect year-round getaway spot to unwind after a day of exploring the area.

Guest favourite
A charming porch area is depicted, featuring a macramé swing chair hung beside a white door. The door displays textured glass panels and is complemented by a black wall lantern. Warm wooden decking enhances the inviting entrance.
Guest suite in Meaford
4.94 out of 5 average rating, 319 reviews

The Beach Button

Cute as a Button, this cozy home inspired by beach house vibes is nestled in the quaint town of Meaford. This town offers some of the most amazing waterfront to explore! 2 minutes east is a spacious public beach, 2 minutes towards the west is the beautiful Harbor or step out the door and enjoy a 3min walk down to the lake! This property is also located a scenic 25min to the famous Blue Mountain Ski Resort! and Scandinave Spa!

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