Creemore / Caledon
Creemore and Caledon vacation rentals offer a refined countryside escape just outside Toronto. This region includes Creemore, Caledon, Glen Huron, and Mulmur. Known for rolling landscapes, scenic views, and understated luxury, it provides a slower pace than traditional cottage destinations.
Our collection of Creemore and Caledon vacation rentals features thoughtfully selected properties designed for comfort, privacy, and relaxed living. From modern farmhouses to countryside estates, these homes are ideal for ski getaways, wellness retreats, and small group stays.
Charming villages, golf courses, and local amenities surround the area. Guests can enjoy year-round recreation, including skiing at Devil’s Glen Ski Club and Mansfield Ski Club. Trails, farm markets, wineries, and dining experiences add to the region’s boutique appeal.
For those seeking space, design, and a slower countryside rhythm, Creemore and Caledon offer a distinctly elevated escape.
Bunker Ridge Farm
- 5 Bedrooms
- 7 Bathrooms
- Sleeps 12
- Pets allowed
incl. taxes and fees
BUNKER RIDGE FARM AREA Nestled amongst the picturesque rolling hills of Creemore on 52 acres, Bunker Ridge Farm is set atop a spectacular lookout on the Niagara Escarpment. Located only 5 minutes outside of Creemore, 20 minutes from Collingwood and 1 hour and 20mins from Pearson Airport, Bunker Ridge Farm is in perfect proximity to all of the major hubs! PROPERTY BUNKER RIDGE FARM - Arrive via a long driveway that winding…
Morning Star
- 5 Bedrooms
- 3 Bathrooms
- Sleeps 14
- Pets allowed
incl. taxes and fees
MORNING STAR AREA Set atop the Niagara Escarpment this stunning Scandinavian style home boasts breathtaking views as far as the eye can see! Located only 5 minutes outside of Creemore, 20 minutes from Collingwood and 1.5 hours from Pearson Airport, Morning Star is in perfect proximity to all of the major hubs! PROPERTY MORNING STAR - Arrive to the picture perfect countryside property via a long driveway lined with new trees. A…
Lavender Hill
- 6 Bedrooms
- 5 Bathrooms
- Sleeps 12
- Pets allowed
incl. taxes and fees
LAVENDER HILL AREA Set in the rolling hills of Dunedin, Lavender Hill is only 5 minutes away from the Bruce Trail and the quaint Village of Creemore. Devil's Glen Country Club and The Blue Mountains/Collingwood are only a short 20 minute drive away! PROPERTY LAVENDER HILL - Nestled on 56 sprawling acres of the Creemore countryside, Lavender Hill offers a very private destination with breathtaking views and high-end amenities. Immaculate gardens welcome…
Burnt Barns Creemore
- 4 Bedrooms
- 3 Bathrooms
- Sleeps 8
- Pets allowed
incl. taxes and fees
Clad entirely in charred cedar, a 4,000-year-old traditional Japanese sustainable building technique called sho shugi ban, Burnt Barns offers renters an extremely unique and relaxing retreat! BURNT BARNS AREA Located 2 km up the hill on Collingwood Street overlooking the quaint town of Creemore, this gorgeous country home offers proximity to all the popular local amenities. Whether you want to shop or eat in town or partake in the many activities available…
Woodlands
- 6 Bedrooms
- 5 Bathrooms
- Sleeps 11
- Pets allowed
incl. taxes and fees
WOODLANDS AREA Located among the rolling hills, valleys, forests and wetlands of picturesque Caledon just north of Mississauga and Toronto. The Paintbrush golf course is across the road and the charming community of Caledon East with it gourmet food shops, cafes, farmers' market, arboretum and extensive gardens is a few minutes drive away. Hiking, biking, cycling and ski trails are also close by. WOODLANDS PROPERTY Approaching the property's front gate takes one…
Orchard House
- 5 Bedrooms
- 5 Bathrooms
- Sleeps 12
- Pets allowed
incl. taxes and fees
ORCHARD HOUSE AREA Mulmur Township is a hidden gem just over an hour north of Toronto Pearson International Airport. Straddled by the famous Niagara Escarpment, a UNESCO World Biosphere Reserve, the area is filled with rich farmlands, steep slopes, river valleys, forests and rolling plains. The charming town of Creemore with its fine restaurants, quaint shops, and famous brewery are just 25 minutes away. Take a day trip to the historic town…
Cimarron Ridge
- 5 Bedrooms
- 4 Bathrooms
- Sleeps 12
- Pets allowed
incl. taxes and fees
CIMARRON RIDGE AREA This modern country home is located in Mansfield, Ontario, approximately an hour's drive north-west of Toronto. Nestled within the beautiful rolling hills of Dufferin Country, Cimarron Ridge offers the perfect location for members of the Mansfield Ski Club, which is located less than a 5-minute drive from the farmhouse. Similarly, Cimarron Ridge is only a 25-minute drive to Devil's Glen Country Club. For day to day needs, guests will…
Wyndsong Farm
- 5 Bedrooms
- 4 Bathrooms
- Sleeps 12
- Pets allowed
incl. taxes and fees
WYNDSONG FARM AREA Located within walking distance of the well-known hamlet of Creemore. Less than 2 hours from Toronto, 25 mins to downtown Collingwood and 30 mins to Blue Mountain. Perfectly situated to enjoy the many nearby ski and golf facilities including Devils Glen and Mansfield ski clubs (both 15 mins drive), as well as an abundance of outdoor activities and walking trails (both on and off the property!). Less than 10…
Splendid Symmetry
- 4 Bedrooms
- 3 Bathrooms
- Sleeps 7
- Pets allowed
incl. taxes and fees
SPLENDID SYMMETRY AREA Located just 10 minutes north of Mansfield Ski Club and Mansfield Outdoor Centre and 10 minutes from the quaint town of Creemore with it's brewery, lovely shops, fine restaurants and local farmers' market. 20 minutes from Devil's Glen Country Club and Devil's Glen Provincial Park. Total privacy and stunning views await. SPLENDID SYMMETRY PROPERTY This charming and unique winter retreat rests on 25 acres of rolling hills and scenic…
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