Holiday rentals with a pool in Dufferin County

Country Family Getaway with Pool and Trails

This charming restored stone farm house with stained glass windows that look out over the well landscaped property with stone walls, heated pool & mature fruit and maple trees. Perfect for a family vacation on nearly 100 acres of private flora, fauna and pristine streams or simply enjoy local cultural offerings . Also an ideal location for special events. A 9-hole golf course and The Bruce Trail, Split Rock Narrows, Dufferin County Forest are among other famed nature reserves just minutes away.

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.

Cozy HotTub & Fireplace-Headwaters Spring 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!

Into the Woods Log Home

Private and relaxing escape, only 1:20 hrs from Toronto, and 40 minutes to Collingwood. Amenities include: - swim spa pool (seasonal) and hot tub - 2 swimming ponds - 70 acres of land (with trails) - sauna and steam shower - pirate ship play structure - ice rink (seasonal) - fireplaces - kids' zip line ... You'll never want to go home! This is our family home. Pls ensure you can abide by our house rules before booking. This also means NO PARTIES. Follow us on IG - intothewoodsloghome

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!

Cozy Alton Cabin | March Break Escape Near Toronto

Escape to our riverside cabin this winter—soak in the hot tub under falling snow, curl up by the fire, and enjoy cozy evenings surrounded by nature. Perfect for couples, families, a ski weekend away, girls’ weekends, or a quiet work-from-home retreat. • 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

Ballo 2-Bedroom Apartment

Charming 2-Bedroom in Orangeville Relax in this cozy, light-filled 2-bedroom apartment with a full kitchen, 1 washroom, spacious living area with Tv, and a dedicated workspace. Perfect for big families or 2 family’s travelling together. Extra sofa-bed available. Enjoy the private backyard with a seasonal pool and garden. Just minutes from Broadway’s shops, cafés, restaurants, the Saturday Farmers Market, and the historic Opera House. Perfect for couples, families, or remote workers.

Indoor Pool • Hot Tub • Heated Dome • 40 min GTA

Welcome to a peaceful 15-acre retreat in Erin, featuring 3+1 bedrooms and 5 bathrooms, plus a year-round heated indoor pool 🏊‍♀️. 🥾 Enjoy scenic woodland trails, a heated indoor sports dome for mini soccer & volleyball ⚽🏐, and an outdoor hot tub with beautiful views over a spring-fed pond 🐟. 🍽️ Complimentary breakfast items included, and support is always available by call or message. Perfect for families and groups —ideal for relaxing getaways, reunions, and nature escapes 🌲

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.

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.