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.

Hot Tub Fall Colours 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!

Private cottage heated pool/HotTub/Games 20 Acre

Nestled in a serene countryside setting, this charming cottage offers a perfect blend of rustic charm and modern comfort. Step outside to discover a private outdoor heated pool and hot tub, each offering a soothing retreat. Whether you’re enjoying a peaceful morning swim or hosting friends for a sunset soak, this cottage with its outdoor heated pool and hot tubs is an idyllic escape for any getaway. Nearby Attractions: - TPC Toronto Opsrey Golf - Hockley Resort Ski/Spa - Provincial Park

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!

Stylish 3BR | Hot Tub • Firepit • Cozy Fall Escape

Welcome to your relaxing escape in the heart of Alton—a cheerful and spacious 3-bedroom, 1.5-bathroom home backing onto the beautiful Credit River. Perfect for families, friend groups, wedding guests, or anyone craving peace, nature, and comfort. • Sleeps up to 8 guests comfortably • 3 cozy bedrooms (2 with private decks!) • 1.5 bathrooms • Fully equipped kitchen + BBQ patio for year-round grilling • Stylish living room with fireplace & smart TV • Fast Wi-Fi, workspace-friendly

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.

The White House

Discover the gorgeous landscape that surrounds this place to stay. It is located in our campground. We just opened it up to you, this is a brand new space. Ideal for 2 people or add in one child that can sleep on the couch. You can have a campfire, time alone, come rain or shine. You can join in on the activities or just do your own thing. Share our public pool, walking trails, volleyball net, pond site.

Spacious 4BR Country Retreat with Fire Pit & BBQ

Nestled in south-central Ontario, our 3000 sq ft home sits on a sprawling 100 acres, blending vintage charm with modern comfort. With 4 cozy bedrooms, 2 living spaces, and a backyard perfect for evenings around the BBQ and fire pit, it's ideal for families. Plus, we're just minutes from ski resorts, golf clubs, and museums. Come make memories with us! Note: Pool is NOT available