Cottage holiday rentals in Richmond Hill

A charming cottage-style home showcases a combination of brick and wood features with a steeply pitched roof. The bright red front door is framed by lush greenery and well-maintained flower beds, enhancing the inviting entryway. A manicured lawn surrounds the home, creating a serene atmosphere.

4.99 out of 5 average rating, 75 reviews

The Gingerbread House | Near Lake + Wedding Venues

This peaceful 3-bedroom cottage combines rustic charm with modern comforts. The open-concept main floor features hardwood floors, a cozy living area with a wood-burning stove, and tons of natural light. The fully stocked kitchen makes cooking easy, and a backyard deck with BBQ is perfect for relaxing after a day by the lake. Fast Wi-Fi and a dedicated desk make it ideal for remote work or school. Whether you’re here for a wedding, a family getaway, or a quiet recharge, you’ll feel right at home.

A covered patio area features a hot tub alongside a glass-topped table with comfortable seating. The peaceful lakeside view showcases expansive green space and a row of chairs positioned along the shore, framed by trees lining the property.

4.97 out of 5 average rating, 96 reviews

Sunset Shores Lakehouse- Hot Tub, Wet Bar & Games

Welcome to Sunset Shores Lakehouse! Nestled in a tranquil bay on the shores of Lake Simcoe, this spacious family lake house is the perfect escape in all 4 seasons with many indoor and outdoor activities to enjoy! This peaceful waterfront retreat boasts 4 bedrooms + Wet Bar + Patio Oasis with lakeside Fire Pit + 6 person Hot Tub overlooking the lake and spectacular daily sunsets and sunrises you wont want to miss! Only 1 hour from Toronto and close to many Georgina attractions and adventures!

A circular patio area features a fire pit at the center, surrounded by eight colorful Muskoka chairs in red and blue. The setting overlooks a serene lake and wooden dock, with a guitar resting nearby on the lawn, framed by a clear blue sky and scattered clouds.

4.91 out of 5 average rating, 296 reviews

Luxury Waterfront Cottage Hot Tub & Amazing Sunset

Private lakefront cottage on Lake Simcoe with hot tub, stunning sunset views, and a rare shallow sandy-bottom waterfront — a unique feature rarely found on the lake. Perfect for large families and group getaways near Toronto, just minutes from Hwy 404. Enjoy swimming, kayaking, paddleboarding, fishing, BBQ, fire pit, and a private dock. Features 6 bedrooms, 4 bathrooms, a chef’s kitchen, and spacious open-concept living. Close to town, yet private, peaceful, and perfect for waterfront getaways.

4.85 out of 5 average rating, 252 reviews

3BR on Lake Simcoe | Gorgeous Views 1hr From City

Escape the city and unwind at our peaceful three-bedroom lakefront cottage on Lake Simcoe, just one hour north of Toronto. With 129 feet of private waterfront, expansive lake views, and shallow swimmable shoreline, it’s the perfect year-round getaway for families, couples, or friends looking to relax and reconnect. 🌅 Stunning sunrise lake views 🏖️ 129 ft of private waterfront 🏊 Shallow, swimmable shoreline 🔥 Cozy all-season retreat 🌲 Quiet and peaceful setting 🚗 Just 1 hour from Toronto

4.95 out of 5 average rating, 153 reviews

Floor-to-ceiling panel doors open to a spacious wooden deck, surrounded by autumn foliage in vibrant shades of orange and yellow. A view of the Nottawasaga River is visible, with fallen leaves scattered across the deck, creating a serene outdoor atmosphere.

Cottage in Mono

Hockley Riverside Cottage • Loft and Bunkie

Needing an unforgettable escape? This cozy cottage is nestled in nature along the Nottawasaga river and has large panel doors that fully open for picture worthy views & peaceful sounds of the river. A new incredible outdoor fire-pit with hanging egg chairs. A cozy indoor wood burning fireplace along with a comfy pull out couch that has a projector above for the best movie nights. Heated floors if you aren't interested in maintaining a fire, fully equipped kitchen, Wi-fi, AC and washer/dryer.

4.91 out of 5 average rating, 74 reviews

A modern kitchen features a large central island topped with a bowl of fruits. Blue cabinetry complements the white countertops, while pendant lights hang above. Natural light flows through windows, illuminating the space and highlighting the stainless steel appliances and charming brick wall in the background.

Cottage in Kettleby

5-BR Home Near Toronto - Large Backyard & Fire Pit

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.

4.85 out of 5 average rating, 26 reviews

Cottage in Brampton

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!

4.81 out of 5 average rating, 113 reviews

A wooden dock extends over a serene pond, featuring two red Adirondack chairs positioned facing the water. Surrounding trees are visible in the background, reflecting gently on the calm surface of the pond under a clear blue sky.

Cottage in Uxbridge

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.

4.93 out of 5 average rating, 40 reviews

Cottage in Parkdale

Cottage in Toronto’s West End •Walk to BMO Field•

A hidden cottage retreat in Toronto’s vibrant west end—just 15 minutes walk to BMO Field with no traffic or crowds. Tucked away on a quiet, tree-lined laneway, this fully renovated 1800s cottage offers a rare mix of charm, privacy, and location. Enjoy the energy of the city—Queen West, Ossington, Liberty Village —then come home to your own peaceful escape. Perfect for World Cup visitors, families, and remote workers. Stay close to everything, without sacrificing calm and comfort.

4.94 out of 5 average rating, 173 reviews

A wooden dock extends into a serene lake, reflecting a clear blue sky with scattered clouds. Flower pots are positioned on the dock, while torches line the edges, contributing to a peaceful outdoor atmosphere.

Cottage in Richmond Hill

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

4.99 out of 5 average rating, 230 reviews

A quaint red cottage is highlighted alongside a rustic barn, surrounded by a wooden fence. Lush greenery and wildflowers accompany the structure, creating a natural setting. The areas are bathed in warm sunlight, enhancing the serene and secluded atmosphere of the property.

Cottage in Palgrave

Hockley valley, up country guest cottage

please read the entire post our beautiful cottage is located on 27 acres of land. Which is very secluded and quiet. Open concept cottage , with a loft bedroom with a double bed, a double sofa bed and a single folding bed. Wood burning fire place and a Small area with a hot plate , microwave, toaster oven, coffee maker , small fridge , BBQ on the porch. Swimming pond Vegetable garden and honey bees. Beautiful wooded trail No smoking Kids are welcome

4.96 out of 5 average rating, 122 reviews

The exterior of a two-story log cabin is illuminated at night, showcasing its natural wood finish and gabled roof. A welcoming entryway features a wooden staircase leading to the front door. Surrounding green grass provides an open space, enhancing the rustic charm.

Cottage in Gilford

Lake simcoe Waterfront Log Cabin near Toronto

*Great for ice fishing on lake Simcoe* Some of the best ice fishing in Ontario, lots of Jumbo Perch, trout, whitefish etc Relax with the whole family at this peaceful place to stay. This two story, modern cottage built entirely of logs and situated on Lake Simcoe is the perfect getaway. Whether you are in the mood for entertainment, adventure, or simple relaxation, this cabin can provide you a comfortable and picturesque stay throughout your visit.

Popular amenities for cottage rentals in Richmond Hill

Kitchen

Wifi

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Cottage in Belfountain

Paradise overlooking the river

A serene lakeside property is nestled among lush greenery, featuring a multi-level structure with a sloped path leading down to the water. Tall trees surround the building, creating a peaceful atmosphere, while the clear blue sky above enhances the tranquil setting.

Cottage in Port Perry

Cheerful 3 Bedroom cottage with hot tub

4.81 out of 5 average rating, 85 reviews

An aerial view showcases a stone cottage-style house with a green roof, surrounded by lush greenery and trees. A winding driveway leads to the property, where two vehicles are parked, set against an expansive green lawn.

Cottage in Goodwood

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

An aerial view of a spacious property showcases a cozy cottage surrounded by lush woodland. A circular saltwater pool is positioned beside the cottage, while a fire pit area with seating is visible on the lower part of the yard, inviting outdoor relaxation.

4.7 out of 5 average rating, 122 reviews

La-Datcha Cottage, Hot Tub, Sauna, Pool, 20 Acres Land

A lakeside property is framed by lush greenery and tall trees. The multi-level building features large windows and a welcoming terrace, with a staircase leading down to the water. A wooden dock extends into the lake, providing access to the serene setting.

Cottage in Port Perry

Cheerful 3 Bedroom cottage

Pet-friendly cottage rentals

A serene view of a calm lake reflects a clear blue sky dotted with fluffy clouds. Lush green trees line the shore, while wooden docks are visible along the bank. The surrounding nature contributes to a peaceful atmosphere.

5 out of 5 average rating, 4 reviews

Cheerful cottage by the lake Lake Simcoe

Cottage in Port Perry

Lakefront Escape • Dock, Sunroom, Games Room

4.88 out of 5 average rating, 25 reviews

Cottage in Seagrave

Relaxing lakeside retreat near a winery & cidery

The exterior of the cottage is depicted, featuring a covered patio area with seating and a flower bed filled with vibrant blooms. Soft lighting enhances the home's facade, while a well-maintained lawn surrounds the structure, providing a welcoming environment.

4.83 out of 5 average rating, 83 reviews

Peaceful Cottage • Close to Lake Simcoe + Fire Pit

The calm water reflects a vibrant sunset with hues of orange and pink. A tranquil shoreline is visible, bordered by lush greenery and the silhouette of trees. The horizon appears expansive, showcasing a blend of colors against a soft, cloudy sky.

Private room in Georgina

4.5 out of 5 average rating, 8 reviews

Private Cozy Bedroom in a Cottage by the Lake

An expansive view of the property reveals a two-story stone house surrounded by lush green fields. A landscaped pathway leads to the entrance, while ample outdoor space and trees provide a serene atmosphere. The surrounding countryside enhances the tranquility of the setting.

Cottage in Limehouse

4.47 out of 5 average rating, 32 reviews

Executive Cottage in a CITY on 100 Acres

Superhost

A tranquil view of Lake Simcoe at sunset is captured, showcasing shimmering golden reflections on the water. The horizon stretches into the distance, framed by lush greenery and smooth stones along the shoreline.

4.69 out of 5 average rating, 52 reviews

Cottage at Lake Simcoe

A serene lakeside view captures a vibrant sunset reflected on the water's surface. Soft clouds are present in the sky, showcasing shades of orange and pink. Lush greenery frames the image, while gentle waves create ripples along the shore.

Private room in Georgina

4.73 out of 5 average rating, 11 reviews

Private room in a beautiful cottage by the lake

Private cottage rentals

Cottage in Kettleby

4.67 out of 5 average rating, 3 reviews

Signature King City Cottage Escape

Superhost

Cottage in East Gwillimbury

4.67 out of 5 average rating, 9 reviews

Watrfrt Cottage | Sunset Views & 45 Min to Toronto

A waterfront cottage is showcased with a striking A-frame architecture. Large glass windows dominate the front, providing views of the surrounding landscape. A welcoming wooden deck features seating, inviting relaxation. Greenery surrounds the property, enhancing the natural setting.