Cottage holiday rentals in Port Perry

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Top-rated cottage rentals in Port Perry

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Guest favourite
Large glass patio doors frame a scenic view of the waterfront, revealing a private deck with seating and a hot tub surrounded by trees. Sunlight casts a warm glow over the area, enhancing the sense of tranquility.
Cottage in Innisfil
4.89 out of 5 average rating, 204 reviews

Stunning Lakefront Cottage Hot Tub & Sauna

.🧘 Relaxing, Quiet, waterfront property with stunning nature. šŸ§–ā€ā™€ļø Experience a private Spa with year round new sauna & new hot tub and amazing view. Please bring your own bath towels! 🤫 A peaceful oasis for families. Please describe your family before requesting to book. Max 6 guests incl children. Absolutely no events, parties, noise allowed. Not for a group of friends šŸ–50’x302’ lot, private dock, gazebo šŸ‘©šŸ»ā€šŸ’»65ā€ smart 4K UHD TV, fast / reliable internet, LCD fridge, filtered water

Guest favourite
Three Muskoka chairs are positioned on a sandy shore, facing towards the calm waters of the lake. The tranquil scene is enhanced by a soft gradient of colors in the sky during sunset, offering a peaceful and inviting ambiance.
Cottage in Brighton
4.89 out of 5 average rating, 332 reviews

Bianca Beach House - EV/Hot Tub/Firepit/Waterfront

Welcome to our Boho Chic Beach House! Get away from it all at this newly refurbished lakeside property with 125ft of private shoreline. Relax in the hot tub, rest your toes in the sand as you listen to the waves break, take the kayaks out, swim in the lake, have lunch on the deck, roast smores at the custom firepit, and take in beautiful sunsets. We have all the modern amenities including EV charger, BBQ, central heating, A/C, washer/dyer, 50" Smart TV with Netflix, high speed LTE Internet.

Guest favourite
Cottage in Harcourt
4.93 out of 5 average rating, 150 reviews

Lakefield Lakehouse /Hot Tub/ Sauna/ Games Garage

Unwind at this private, pet-friendly, all-season lakefront cottage with 4 bedrooms and 2 full bathrooms—ideal for families or small groups looking for a relaxing getaway. Just 5 mins from Lakefield’s shops, cafes, spas & a local chocolate factory. Thoughtfully designed & fully stocked for a cozy, carefree getaway. Sauna is wood burning to use start a fire in chamber and let burn for 30 minutes Hot Tub added May 2025 (up to 7 ppl) We only accept bookings from guests with positive Airbnb reviews

Top Guest favourite
Cottage in Trent Lakes
4.99 out of 5 average rating, 159 reviews

Panoramic Lake Views Inside & Out, Cozy & Relaxing

Enjoy panoramic views of Lower Buckhorn Lake with the family! Relax perched in the hot tub atop the rocks of the Canadian Shield, nestled among the tall pines. This newly updated waterfront cottage features 3 bedrooms & an open concept living space. Over 280 feet of waterfront for you to enjoy the sunrise & sunsets & fish off the dock! Get cozy on the couch, play games, or watch movies. Take a stroll around the island. Hi speed Wi-fi to work or play. 6 minutes to town, less than 2 hrs from GTA.

Top Guest favourite
Cottage in Keswick
4.91 out of 5 average rating, 293 reviews

Luxury Lakefront Cottage | Hot Tub & Sunset Views

Private lakefront cottage on Lake Simcoe with hot tub, sunset views, and a rare shallow sandy-bottom waterfront — a unique feature that’s hard to find. Ideal for large family and group getaways near Toronto, just a short drive from Hwy 404. Enjoy swimming, kayaking, paddleboarding, BBQ, firepit, private dock, fishing, and lakeside fun. Spacious 6 bedrooms, 4 bathrooms, a chef’s kitchen, and open-concept living make it perfect for relaxing and gathering. Close to town, yet private and peaceful.

Guest favourite
Cottage in Innisfil
4.85 out of 5 average rating, 249 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. šŸŒ… Stunning sunrise lake views šŸ–ļø 129 ft of private waterfront šŸŠ Shallow, swimmable shoreline šŸ”„ Cozy all-season retreat 🌲 Quiet and peaceful setting šŸš— Just 1 hour from Toronto

Top Guest favourite
Cottage in Cobourg
4.98 out of 5 average rating, 353 reviews

Forest Retreat: Couples Escape w Hot Tub Fireplace

Slow mornings. Forest surround. Soak under the stars. Described by Narcity Canada as ā€œLike Living in the Holidayā€ Praised as a couple's getaway, near Ste. Anne's Spa. Follow us @coachhouse_cobourg Step into a 150-year-old coach house nestled on a stunning 5-acre Victorian estate. This beautifully restored guest house combines historic charm with modern comforts, offering a private hot tub, a cozy fireplace, and a serene escape minutes from Cobourg’s vibrant downtown and pristine beaches.

Guest favourite
Cottage in Georgina
4.95 out of 5 average rating, 124 reviews

Resort-Style Luxury Waterfront Cottage

Experience luxury at our 5-star, Superhost-rated waterfront cottage on Lake Simcoe, just 80 KM from Toronto! A guest favorite, it offers breathtaking sunsets and sunrises from the living room and loft. Relax on the sandy beach with waist-deep waters, and enjoy the patio, BBQ, bar, lounge, kayaking, and fishing. With a fully equipped kitchen, 3 bedrooms, and 2 bathrooms, it comfortably accommodates up to 8 guests. Book your dream getaway today for the perfect blend of relaxation and adventure!

Superhost
A wooden dock extends over the calm water, adorned with two red Adirondack chairs facing the lake. A grassy area is visible with seating and a tree providing shade. The cottage can be seen in the background under a clear blue sky, enhancing the outdoor setting.
Cottage in Kawartha Lakes
4.85 out of 5 average rating, 127 reviews

Little Blue Lakefront Cottage on Sturgeon Lake!!

Beautiful waterfront cottage on Sturgeon Lake. Super spacious feel w/ 2 BR to sleep up to 5.Gourmet kitchen w/ high end appl, large dining table sits 6. Relax & BBQ on comfortable deck w/ beautiful lake views and table to seat 6. Enjoy the fire-pit on the Muskoka Chairs. Important Note: Dock is usually ready for first week of May every year. Could be earlier depending on the weather. Also the City of Kawartha Lakes has a NO BONFIRE ban during April each year. So please do not do a BONFIRE.

Top Guest favourite
Cottage in Caesarea
4.99 out of 5 average rating, 101 reviews

Lakeside Cottage Getaway South Shore Lake Scugog

WELCOME TO YOUR LAKESIDE GETWAY! This ALL SEASONS rustic, private lakefront cottage (south shore of Lake Scugog) has 2 bedrooms, 2 queen sized beds, large bright living/dining room, pullout couch, newly renovated kitchen and bathroom, private dock, indoor fireplace/outdoor fire pit and a loft space. Located approximately 1.5 hours from Toronto, this cottage is the perfect place for families and friends to escape the hustle and bustle, relax and unwind.

Top Guest favourite
Cottage in Kinmount
4.94 out of 5 average rating, 314 reviews

Secluded Cottage on a Private Lake

2 bedroom cedar log cottage on over 300 beautiful acres. Very private. Many walking trails to explore and enjoy. Lovely deck on the cottage and a great dock at the lake. Canoe, pedal boat, and swimming raft. All just a 2 hour drive from Toronto. We have another property at the opposite end of the private lake - all of the same wonderful outdoor activities but this time based out of a stunning log house. Check it out under other Kinmount listings!!

Guest favourite
The exterior view of the cottage showcases a stone facade illuminated by string lights as twilight approaches. A welcoming deck area features seating for relaxation, while natural surroundings provide a tranquil atmosphere. Steps lead down to the path, enhancing accessibility to nature.
Cottage in Havelock
4.92 out of 5 average rating, 118 reviews

Rowan Cottage Co. on Oak Lake

Nestled among the trees, you’ll find Rowan Cottage Co. on Oak Lake—just 2 hours from the GTA and 3 hours from Ottawa. This newly renovated, design-forward cottage is thoughtfully curated and surrounded by nature, with modern amenities that make it feel like home. The interior, decks, and dock all enjoy southeastern exposure, filling the space with natural light and offering beautiful views across 125 feet of lake frontage on a semi-private lake.

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