Loft holiday rentals in Grey Highlands

Hockley Haven

Kick back and relax in this calm, stylish space. Newly renovated cozy 1 bedroom carriage house loft (appx 650 sq ft) above detached 3 bay garage in serene country setting on 5 acres of pine and cedar with a river running thru it. Pullout couch can accommodate 2 additional people. Walk across the road to Pollinator Garden & Island Lake Trails. 6 min drive to Hockley Valley Resort and Adamo Estate Winery, as well as beautiful downtown Orangeville boasting fabulous restaurants and quaint shops.

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.

Home Away From Home at Blue - Renovated Clean Loft

Professionally cleaned and recently renovated Loft at North Creek Resort on the north side of Blue Mountains. Steps to ski slopes/north lift chair & Toronto Ski Club. 15-20 min walk - 2 min drive to the Village. 15-20 min walk - 2 min drive to Northwinds beach. 15 min drive to Collingwood - access to restaurants & grocery shops. Easy access to biking/hiking trails. Free parking. TV/Internet included. Free seasonal outdoor pool & jacuzzi & tennis/pickle ball courts. Wasaga Beach 25-35 min.

2 Queen Bedroom Loft with laundry and kitchen

Come and explore the Collingwood area! Now dog friendly. We are close to everything - Blue Mountain, Wasaga Beach, Golfing, Collingwood Rail Trail, and so much more. Spacious, private, air conditioned apartment loft at the newly rebuilt Batteaux Schoolhouse. This modern space has been carefully designed to accommodate a maximum of four people. Enjoy nature through all the oversized windows and on your private deck. Parking on the property for up to two cars with your own private entrance.

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

Sunshine Summit - Outdoor Pool / Shuttle to Blue

Sunshine Summit is a bright loft located in North Creek Resort at the North Base of Blue Mountain. Ideal location for those seeking easy access to the ski hills and hiking trails but still within minutes to Blue Mountain Village. North Creek resort offers a free shuttle service to Blue Mountain Village, an outdoor swimming pool open in the summer months, hot tub year-round, tennis courts with night lights, charcoal grills and community picnic tables that you can use during your stay.

Mountainside Escape - Shuttle, Pool & Hot Tub

Mountainside Escape is located in the North Creek Resort at the North Base of Blue Mountain. Ideal location for those seeking easy access to the ski hills and hiking trails but still within minutes to Blue Mountain Village. North Creek resort offers shuttle service to Blue Mountain Village, an outdoor swimming pool open in the summer months, hot tub year round, tennis courts with night lights, charcoal grills and community picnic tables that you can use during your stay.

Brand New Country View Loft with Hot Tub

Conveniently located between Owen Sound and Meaford on a beautiful 7 acre property surrounded by fields and trees, this brand new bright and open loft has endless attractions within a 50 km radius. Whether you are a skier going to Blue Mountain or want to enjoy the beach at Sauble, this place can be your home base while you explore our wonderful area. Coffin Ridge Winery:5 mins, Blue Moutains:30mins, Bruce Trail:5mins, Sauble:30mins, Bruce Penninsula:45mins.

Nest By The Bay - Downtown Midland / Private Loft

Luxury, Comfort & Style. This one-of-a-kind rental, "Nest By The Bay", is located in Downtown Midland. Walk everywhere, park your car & enjoy what Midland has to offer. Midland Harbour is only minutes by foot. Live our lifestyle, enjoy our many festivals, professional theatre, artisans, culinary cuisine, seasonal events & so much more! See our other listing "Perch By The Bay", also at this same location. Listing not suitable for ages under 6.

Sunflower Loft

Kick back and relax in this calm, stylish space, surrounded by bright light, wooded forest, a pond with a fountain and garden views. Sit back and enjoy a cup of coffee or wine on our large deck overlooking the forest while enjoying the sounds of the birds. If you like being outdoors there is a firepit to enjoy with that glass of wine! We now have a dedicated space for a firepit and hammock!

Hilltop View Farm

Just ten minutes north of Mount Forest on Hwy 6 sits our yellow brick farmhouse on top of a hill allowing a lovely view over fields and forests. After a stroll down to the pond one can relax on the patio and listen to the sound of nature. For the golfer there is a 9 hole course 600 meters down the road. Nearby villages offer conservation areas, shopping,restaurants and an art gallery.

Slopeside Terminal - Shuttle, Pool & Hot Tub

Celebrate the holidays in comfort at our cozy Blue Mountain condo. Decorated for the holidays with a tree, and warm seasonal touches, it’s a relaxing place to enjoy the holiday season. After a day on the slopes or exploring nearby trails, come back to unwind and watch a holiday movie with a warm drink. Holiday decorations will be up from December 1st, 2025 - January 4th, 2026.