Holiday rentals with a pool in Dufferin County

Sunny Pines Farm Studio Tennis Court/Bruce Trail

Perfect for a getaway in the country. A bright, spacious, open-concept designer studio featuring beautiful rolling-hill vistas, queen bed, 3-piece bathroom, dedicated bbq, heat/AC plus a wood burning stove, wet bar with a Nespresso machine, deluxe counter-top oven & bar fridge and all new tennis court, laundry available upon request. Mono Cliffs, Boyne Valley, Hockley Valley Nature Reserve Prov. Parks & Mansfield Recreation Centre are minutes away. Ideal hiking, cycling, snowshoeing and xcsking.

HotTub & Pool Getaway - Headwaters Retreat

Escape to our rustic-modern Queen Suite, perfect for your getaway. Relax in the private hot tub right outside your door, unwind by the fireplace & enjoy Netflix & Amazon TV. This cozy retreat features a private entrance, ensuite bathroom, and a second bedroom with twin beds. Steps from scenic hiking trails, minutes from the town center, your stay is ideal for outdoor adventures, wine tours, weddings, work trips or just quiet escape away. Book now for your ultimate getaway in comfort and nature!

Hockley Valley - Jazzy Pines - 4 BR with Pool

Welcome to your private retreat in the heart of Hockley Valley! Nestled on 9 acres of rolling countryside, this unique two-story home offers breathtaking views, direct access to nature trails, and a perfect blend of rustic charm and modern comfort. The great room boasts floor-to-ceiling cathedral windows, flooding the space with natural light and offering panoramic views of the surrounding landscape. Step outside to your own oasis: a newly renovated pool, expansive deck, and landscaped grounds.

Mono Springs - Dream Country Escape w pool/hot tub

Welcome to Mono Springs! Our straight-out-of-a-storybook family retreat, located in the heart of Mono. Lovingly renovated with all new furnishings, this dream country escape with rustic finishes sits on 10 acres of gorgeous landscape and fields with pre-made trails ready to explore giving wholesome Cottage-Vibes. Plenty of space for everyone with lots of quiet sitting areas, both inside and outside, private hot tub and heated pool. Ideal setting for family get togethers and nature enthusiasts

The Trails Retreat (Private Cabin)

Beautifully renovated 2-story private hilltop cabin for romantic getaway, family stay or friends' retreat, experience a taste of the country together. Backed by forest and trails and set away from our family home, minutes to the Bruce Trail, Hockley Ski & Golf Resort, Mansfield Ski Club and charming Orangeville. Enjoy total guest privacy & spectacular sunrises. Guests are welcome to share our heated pool in season:) Add a playful Yoga/Functional Movement class or chef's dinner to your stay!

Hilltop on Cedar Lane

Discover our special retreat, just 12 minutes from the picturesque Hockley Valley Resort, where you can enjoy skiing, golfing, and a luxurious spa. Only 13 minutes from the Mansfield Ski Club, our location offers easy access to thrilling winter and summer sports. Nestled near the Mono Mills Trails, it’s the perfect spot for outdoor enthusiasts. Enjoy a relaxing and convenient escape from the city, blending comfort with adventure. *****Pool will be open and available for use May 25*****

Spacious Getaway w/ Swiming Pool & hot tub

Escape to your own private paradise with this stunning 4 BED, 3 BA (5 queen beds and 4 folding beds) on 8 acres of lush greenery. Perfect for large families or groups of friends seeking fun and tranquility. Relax in our brand-new hot tub, take a dip in the in-ground pool, or explore the private walking trail. Enjoy five cozy queen beds, an open-concept living and dining room, a foosball table, a spacious pool table room, and ping-pong. Book now for an unforgettable experience!

Luxury Hockley Estate Spa

Kick back and relax in this calm, stylish space. This home is located in a central location close to Orangeville and hockley Valley ski/ winery/hiking. The home is just like a relaxing spa with pool, hot tub, sauna, indoor wood burning stove, outdoor BBQ, massive kitchen, lots of space. Great for family dinners and getaways, we enjoy groups with longer stays and will give monthly discounts.. This amazing property has it all:)

Stunning Family Retreat, 1hr from TO, Sleeps 15

Nestled in Mono, this serene 5-star retreat estate is a guest favourite, just under an hour from Toronto, and accommodates 15. It is only 10 minutes from Hockley Valley Ski Resort and features private access to Island Lake for snowshoeing and skating. Enjoy Beautiful Summer days by the pool in a setting where luxury blends with comfort, creating the perfect backdrop for relaxation and feeling right at home.