Cottage vacation rentals in Keswick

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.

4.87 out of 5 average rating, 222 reviews

Stunning Lakefront Cottage Hot Tub & Sauna

.🧘 Relaxing, Quiet, waterfront property with stunning nature. 🧖‍♀️ 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 🏖50’x302’ lot, private dock, gazebo 👩🏻‍💻65” smart 4K UHD TV, fast / reliable internet, LCD fridge, filtered water

A dining table is set with decorative blue and white dishware. In the background, a fire pit is surrounded by red chairs, with vibrant greenery and a wooden swing adding to the outdoor ambiance. A flower arrangement and candles enhance the table setting.

4.96 out of 5 average rating, 103 reviews

Greystone cottage in Innisfil

Welcome to our charming cottage in Innisfil, just a short walk from beautiful Lake Simcoe. Enjoy a spacious backyard featuring a cozy fire pit, a peaceful swing, bicycles and a BBQ area perfect for relaxing evening. You’ll find a fun game room equipped with AC, pool table, air hockey for entertainment during your stay. Conveniently located near grocery stores, Home Hardware, restaurants at Friday Harbour, and other local amenities. Come experience the beautiful atmosphere with your loved ones.

4.96 out of 5 average rating, 105 reviews

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.

Cottage in Georgina

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!

4.86 out of 5 average rating, 270 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

4.94 out of 5 average rating, 302 reviews

A circular stone fire pit is surrounded by wooden Adirondack chairs, offering a cozy gathering space. A vibrant fire burns in the center, with lush greenery and a serene riverside view in the background under a colorful sky.

Cottage in Wasaga Beach

Charming riverside cottage, B&B license

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!

4.96 out of 5 average rating, 143 reviews

Cottage in Georgina

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!

4.95 out of 5 average rating, 165 reviews

An open concept living area showcases large panel doors that fully open to the outdoor deck. Inside, a comfortable seating arrangement is visible, along with a cozy area rug and a neutral color palette. Natural light floods the space, enhancing the connection to nature.

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.

4.92 out of 5 average rating, 209 reviews

The exterior of the house displays a stone facade, framed by trees and greenery. A large deck extends from the structure, featuring outdoor seating and a BBQ setup. Nearby, a driveway accommodates several vehicles, with spacious lawn surrounding the property.

Cottage in Georgina

Pearl by Lake Simcoe - with sauna and steam room

Spacious and bright newly renovated house with access to the lake. This 2700 sqf house has a very functional and beautifully decorated living/dining area, 2 state of the art kitchens, 6 cosy bedrooms and 3 full washrooms. Huge 400 sqf deck with BBQ and heater comfortably fits a large company outside. Enjoy indoor sauna and steam room for deep relaxation. Free Wifi. Large entertainment room with Smart TV, XBox, Kinect and a foosball table provide plenty of activities inside the house.

Superhost

An outdoor seating area features a circular arrangement of comfortable furniture, including a low table and spacious couches with light-colored cushions. Black wooden chairs provide additional seating. The background shows a grassy area leading to the water, with trees and a trampoline visible in the distance.

Cottage in Gilford

4.88 out of 5 average rating, 100 reviews

Lake Side Manor With Games Room

Huge Lakefront Retreat – Perfect for Multi‑Gen Family Getaway with Private Beach, Fire Pit & Games Room, 4 King Suites (3 with dedicated ensuites) - 9 Beds in total! Enjoy 3x kayaks, canoe & paddle boat, plus a games room (ping pong, air‑hockey, foosball). Central AC, Wi‑Fi & free parking for 6 cars. Partnered with Muskoka Wake for watersports & Harbour House Kitchen for private dining or catering. Pet friendly. Book now for the ultimate lakefront vacation, just 45 min from Toronto.

Superhost

The exterior of the cottage displays a modern architectural design with large floor-to-ceiling windows, allowing for ample natural light. A spacious wooden deck surrounds the front, featuring lush greenery and vibrant flowers, creating an inviting atmosphere for relaxation.

4.87 out of 5 average rating, 372 reviews

Crystal Beach Cottage & Spa

**New Boat Launch 2026 In front Of Property** Serene lakefront cottage with breathtaking views! This cottage fronts on the East side & faces West for a mesmerizing sunrise & sunset. A few steps to the lake for a dip in the lake, sun bathing, paddle boarding (4 paddle boards) or a stroll up Innisfil Beach Park for a walk. An outdoor fire pit, sauna and hot tub awaits you at to relax and loosen up those muscles & release tension. A wonderful experience awaits you!

4.94 out of 5 average rating, 132 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.