Cottage holiday rentals in Richmond Hill

202519 Oh Canada! Home Away from Home!

Spacious 6 Bedrooms 3.5 Bath with 1 King, 2 Queen, 4 Single Beds & Sofa Bed = Total 14 Sleeping Capacity! Open Concept Kitchen-Living-Dining: Convertible Sofa Bed! Bedroom 1 With King Bed Attached Bath: Bath Tub, Standing Shower! Bedroom 2 Queen Bed Jack n Jill Bath: Toilet & Shower! Bedroom 3 Queen Bed Jack n Jill Bath: Toilet & Shower! Bedroom 4 Two Kids Beds; Specially Designed Kids Space! Bedroom 5 Queen Bed with Walk-in closet & Large Window! Bedroom 6 Two Single Beds & Dedicated Workspace!

Cottage at Lake Simcoe

Escape to this charming bungalow at Lake Simcoe's south end, where you can relax on the covered deck with built-in BBQ and bar sink, garden shed, and ambient lighting. With 4 spacious bedrooms, 2 master ensuites, and a large family room, there's plenty of room for socializing. Enjoy fishing, swimming, and boating just steps away, and visit nearby Willow Beach (15 min drive), Orchard Beach Golf and Country Club, and Beach Lakefront Bar and Grill (8 min drive). Private beach(Pine Beach about 1km).

The Cottage in High Park - free Parking

Escape to our city oasis! Nestled in High Park/Bloor West Village, our charming cottage offers urban tranquility just 15 mins from downtown by subway. Ride a bike to the beach, wander the tree-lined streets, explore boutiques in the local village, or forest-bathe deep in the trails of High Park. Return to cozy comfort, a wood-burning fireplace, a game of charades, or step out to a covered patio, perfect for BBQ creations or a movie under the stars. Your urban-cottage escape begins here!

Family fun! Hot tub/snooker table/Movie Room!

Late check in Dec 30 or early Dec 31 available! Discounts for 3 or more nights. Our house is built like an old English-style stone house cottage and is approximately 1 hour from downtown Toronto. The house is great for special occasions and getting away from it all with a group of friends or family. We've included some fun extras such as a projection theater room, slate snooker table, cable TV, BBQ and an outdoor hot tub. We supply seasoned firewood for the indoor wood fireplace, so have fun.

Gorgeious 5 Bedroom Countryside Cottage in King ON

Gorgeous 5-Bedroom Countryside Cottage - located in a quiet family neighborhood at a beautiful 3-acre lot with a huge lawn and woodlot, Lots of Parking, a minute's drive to The Manor Event Center, Hwy 400 & 427, groceries, restaurants, Golf Club, beautiful trails, Green Belts, farmers markets, Apple and strawberry picking. 20 min. to Lake Simcoe boating and fishing, many nearby shopping malls, TTC Subway, Go Station, and Canada's Wonderland. Please Note: Strictly no drug and booze parties.

Rustic 5BR Cottage | Cozy Hot Tub+ Autumn Backyard

Escape to nature in our private 5BR and 4WR riverside cottage – perfect retreat for groups with premium amenities! ✓ Entire cottage to yourself – full privacy! ✓ 5 spacious bedrooms with 6 double beds and 4 washrooms ✓ Cozy Family & Living Rooms ✓ Fully equipped kitchen & High-Speed Wi-Fi ✔ Dining area with seating for 8 guests ✓ Private Backyard with hot tub & Indoor games ✓ Scenic riverfront setting near Eldorado Park ✓ Safe neighborhood Book your stay and make unforgettable memories!

Cozy Hobby Farm Cottage in Uxbridge

*4 SEASONS COTTAGE*Stunning cottage retreat at Uxbridge,where you can enjoy the perfect balance of tranquility and entertainment.Our 4-bedroom cottage sleeps up to 12 guests, it's the ideal location for families or groups of friends looking to unwind and make lasting memories. You can also take advantage of our BBQ space,you can grill up mouthwatering burgers and steaks while taking in the fresh country air.The barn is not part of the rental and there are no animals inside or in property.

Blue1 House! Signature King City Cottage Escape

Escape to this charming 3+2 bedroom cottage-style home nestled on a large, tree-filled lot in beautiful King City. Surrounded by nature, the home offers the peaceful feeling of a private retreat—while still being just minutes from everyday essentials. Wake up to birdsong, enjoy your morning coffee among mature trees, and unwind in the quiet serenity. Whether you’re planning a weekend escape or a family stay, this home delivers the best of both worlds: nature, comfort, and convenience.*

Priv Magical Forest Manor 30+Disco KTV Party Room

Privacy Manor, 15 Acres Forest Surrounded, over 30+ disco party room & KTV system, waterfall, fountain, outdoor kitchen, short-term stays, retreats and small events. 4000ft interlocking can set a outdoor event. Close golf course and ski resorts, at Uxbridge Perfect for families looking to make the most of the season or for companies wanting to host a corporate retreat. Our Magical Forest Manor is able to host up to guests inside the Cottage. Extremely private with an elevated view.

La-Datcha Cottage,Hot Tub,Sauna,Pool,20 AcresLand

Wake up to birdsong 🌲 and sip your coffee surrounded by peaceful forest views. This private 20-acre escape in Innisfil is your family’s playground for rest, reconnection, and relaxation. Swim, soak, explore—your unforgettable getaway starts here. ✅ 20-acre private woodland in Nottawasaga Conservation Zone ✅ 5 min – Belcroft Estates wedding venue ✅ 10 min – Innisfil Beach Park, grocery stores, & local shops ✅ 20 min – Tanger Outlets & Friday Harbour ✅ 1 hr – Toronto

White Oak on Wilcox-Richmond Hill Lakefront Oasis

Welcome to The White Oak on Wilcox - a lakefront oasis in the heart of Richmond Hill, perfect for an all-season getaway. Located just 30 mins from Toronto, enjoy direct access to Lake Wilcox with beautiful sunset views from the private dock. This vacation home welcomes you to a relaxing and serene lakefront experience. Surrounded by numerous activities to enjoy year-round, this is the perfect home-away-from-home! Share your memories with us @whiteoakcottageco

Watrfrt Cottage | Sunset Views & 45 Min to Toronto

Bright 3-bed, 3-bath custom waterfront cottage home just 40 mins north of Toronto! Sleeps 8 with a king, 2 queens & a futon. Modern kitchen, open living space, and private backyard with dock, fire pit and pergola lounge. Canoe included for water adventures. Enjoy sunsets, relaxing by the water, by the bon fire, and creating memorable moments in a peaceful, private setting while being just 10 minutes away from downtown Newmarket.