Cottage holiday rentals in Port Perry

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Top-rated cottage rentals in Port Perry

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Guest favourite

Cottage in Brechin

4.92 out of 5 average rating, 159 reviews

COTTAGE ON LAKE SIMCOE -4 BEDROOMS /2WSHRMS

Welcome to our cozy cottage in Simcoe County, just a short drive from Toronto. It's the perfect spot for bringing together family and friends. Here, laughter fills the home, and nature's beauty is right outside your door. Dive into clear waters for some fun kayaking and boating, and wake up to beautiful sunrises from our private dock. Take a walk on scenic paths, enjoy outdoor BBQs, and paddle around in our kayaks. Book your special getaway today and start making heartwarming memories that last.

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Cottage in Brechin

4.85 out of 5 average rating, 107 reviews

Lakefront Cottage with Gorgeous Sunset Views

Cozy cottage with gorgeous views right on the lake. Perfect lake for water play, great fishing right off the dock, plenty of nature trails and boat launch nearby. Enjoy your evenings as you take in the sunset around 1 of 2 firepits, whether you choose to have a fire right at the water's edge or up top. There is also a boathouse you can relax on top of under the shade of the trees. Enjoy eating outside on the oversized deck as you take in the views of the lake. Lots of outdoor space to play.

Guest favourite

Cottage in Innisfil

4.95 out of 5 average rating, 102 reviews

Innisfil retreat: Hot Tub, Sauna, Game room

Welcome to our serene Lakeside Retreat in Innisfil, a haven of relaxation and fun. This getaway features a rejuvenating sauna and hot tub, perfect for unwinding after a day of adventure. Entertain with family and friends in our game room, which includes a pool table, air hockey table, and dartboard. The large outdoor deck is ideal for BBQs, complemented by a cozy fire pit for evening relaxation. The house offers five beautifully appointed bedrooms, ensuring comfort for everyone. Water softener.

Guest favourite

Cottage in Ennismore

4.91 out of 5 average rating, 107 reviews

Luxury Modern Cottage Best Sunrises with Hot Tub

*4 SEASONS COTTAGE*Newly built custom luxury cottage, with brand new beds, mattress, furniture and furnishings. Cottage right on the lake , great fishing right off the dock, amazing boating, east exposure provides the best sunrises right from master bedroom, bon fires lake side, all bedding, linen and towels provided, all life jackets provided, tankless BBQ, ice fishing is available in winter, large hottub, pool table, ping pong, enjoy the canoe, kayaks and SUP. Quarry Golf Club is 5 mins away.

Guest favourite

Cottage in Victoria Harbour

4.81 out of 5 average rating, 189 reviews

Serenity, Simplicity and Stone

This is a tiny cottage in a sleepy little hollow that opens onto the Georgian Bay. Inside, each stone was carefully chosen and the woodwork was built, piece by piece, by two craftsmen who are highly skilled and passionate about repurposing. It's an art that will leave you in awe; especially if you're worried about climate crisis. The coat hangers are upcycled 100-year-old railway spikes! If you're looking for luxury you will be disappointed but if you're a minimalist you're going to love it.

Guest favourite

Cottage in Wasaga Beach

4.94 out of 5 average rating, 233 reviews

Charming riverside cottage, walk to beach

Charming riverside cottage available on Wasaga Beach. Just a 4-minute stroll from a pristine sand beach. Immerse yourself in nature's beauty while enjoying modern amenities, including a private hot tub for relaxation. Unwind with a friendly round of mini-golf or gather around the fire pit for cozy evenings under the stars.Create lasting memories at this perfect oasis that combines riverside tranquility, mini-golf fun, hot tub relaxation, and the warmth of a fire pit. Your dream getaway awaits!

Superhost

Cottage in Peterborough

4.81 out of 5 average rating, 162 reviews

Hot Tub+Games Room | Waterfront Cottage, Kawarthas

Relax and enjoy some well deserved time in our private and newly furnished 4 season cottage. Located just a 5 min drive to the charming town of Lakefield, Kawartha Lakes, you will find our cozy cottage right on the water. • Private Waterfront • Hot Tub (open year round) • Games room • High Speed Fibre Wifi • Gas Fireplace • Office workspace • Pet friendly *Please note that we only accept bookings from those who have positive reviews from prior Airbnb stays on their profile

Top guest favourite

Cottage in Kinmount

4.94 out of 5 average rating, 296 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!!

Superhost

Cottage in Tiny

4.81 out of 5 average rating, 154 reviews

Tiny Beach Cottage

Beautiful, newly-renovated 3 bedroom cottage. All of the modern comforts of a home while maintaining the cottage feel you expect when trying to escape the busy city life. Situated on a "no exit" road resulting in a peaceful and quite area. Cottage has a central air conditioning and furnace ideal for all seasons. Featuring two large decks, perfect for outdoor dining or relaxing. Licence STRTT-2025-103

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Cottage in Tiny

4.86 out of 5 average rating, 219 reviews

Georgian Bay Cottage - 100 Acres & Private Beach

THIS IS NOT a waterfront cottage, but it includes a separate PRIVATE gated beach LAKEFRONT property for your EXCLUSIVE USE! Our private two-acre gated beach at Marks Point, the western tip of Thunder Beach, is ten minutes by car from the cottage. The second beach option (public) is the unsurpassed 3km sand Thunder Beach, 5 minutes by foot! The cottage is on our private 100 acres.

Guest favourite

Cottage in Lafontaine

4.83 out of 5 average rating, 241 reviews

Beach house (with pool open May-Oct)

Georgian Bay Beach club. Cute cottage perfect for families, couples, or anyone wanting to relax! 2 bedrooms, 1 bathroom, furnished, pool and private beach on the shores of beautiful Georgian Bay! Cottage is part of a 12 cottage community that shares the pool and beach area. Always super clean, professionally cleaned after every guest! Note: pool is closed October to mid May.

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Cottage in Harcourt

4.92 out of 5 average rating, 60 reviews

Modern Yellow Cottage Harbourtown Marina

Newly renovated year round cottage over looking beautiful Stoney Lake at McCracken's Landing. Steps from Hobart's restaurant, water rentals and general store. A cozy upscale modern furniture and decor. Includes private patio, screen porch, air conditioning, WIFI and satellite flat screen TV. It doesn't get any better that this! Boats and boat slips available upon request.