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Cottage holiday rentals in Simcoe County

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Top-rated cottage rentals in Simcoe County

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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

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

4.87 out of 5 average rating, 222 reviews
Top guest favourite
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.
Cottage in Innisfil

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, 104 reviews
Top guest favourite
The exterior of a modern cottage is framed by tall trees and colorful foliage. A spacious deck wraps around the cottage, providing outdoor seating options. The gravel pathway leads to the entrance, surrounded by natural landscaping and decorative stones.
Cottage in Tiny

Fall Escape - dazzling colours & stunning beach

Insta: @woodwardbythebeach 3min walk to the area’s most beautiful beach, sunsets & trails, you'll be sure to get lost in the serenity of the sand dunes year round Outdoor fire pit- s'mores included! Enjoy the BBQ, deck, & patio; the wine is on us! Fast WIFI for streaming movies or work from cottage Area is secluded yet central. 10min to Midland, close to Balm Beach - arcade, gokart, restaurant, & bar Ski/Hike/Snowmobile then unwind in a peaceful winterized home getaway with indoor fireplace

4.97 out of 5 average rating, 133 reviews
Guest favourite
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!

4.96 out of 5 average rating, 106 reviews
Top guest favourite
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!

4.94 out of 5 average rating, 303 reviews
Guest favourite
A peaceful beach scene captures the soft sand shoreline leading to the water's edge. Gentle waves lap at the shore, and the sky is filled with warm sunset hues. A cottage is visible in the background, nestled among trees, enhancing the serene atmosphere.
Cottage in Tiny

Ultimate Georgian Bay Vacation Getaway

Come and stay at our beautifully renovated *all-season* beachfront cottage and enjoy a breathtaking panoramic view of Georgian Bay! You'll discover the cottage sitting atop a sand dune, right on one of the most stunning freshwater beaches in the world. This rare location hosts a private covered deck hovering over the white sand, in a beach house closer to the bay than anywhere else around! Summer guests also enjoy use of a heated salt water pool and large resort deck created by Paul Lafrance.

4.96 out of 5 average rating, 182 reviews
Top guest favourite
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!

4.96 out of 5 average rating, 145 reviews
Top guest favourite
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.

4.95 out of 5 average rating, 167 reviews
Top guest favourite
Cottage in Georgina

Lakefront | Private Dock, Sandy Beach & Hot Tub

Lake Simcoe waterfront cottage with a rare shallow sandy-bottom shoreline, private dock, and hot tub. Enjoy swimming, kayaking, paddleboarding, fishing, BBQs, fire pit evenings, and breathtaking sunsets. Perfect for family vacations, holiday getaways, and groups near Toronto, just minutes from Hwy 404. Features 6 bedrooms, 4 bathrooms, a fully equipped kitchen, and spacious indoor and outdoor areas. Private, peaceful, and ideal for year-round Lake Simcoe getaways.

4.91 out of 5 average rating, 304 reviews
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.
Cottage in Innisfil

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!

4.87 out of 5 average rating, 373 reviews
Top guest favourite
A stone patio leads to a sandy beach, featuring a seating area with red chairs overlooking Georgian Bay. The calm water is visible in the background, framed by trees and large rocks, with yellow kayaks positioned along the shore.
Cottage in Tiny

Beautiful Beachfront Cottage.

Township of Tiny License Number: STRTT-2026-110 Enjoy our all-season paradise only 1.5 hours north of Toronto! In summer, enjoy the sandy beach waterfront with incredible views of Georgian Bay with the Town of Penetanguishene, and all its historic charm, only 20 minutes away! In winter, enjoy all the area has to offer with incredible OFSC groomed snowmobile trails and amazing ski resorts less than an hour away! *Contract to be sent and signed prior to stay.

4.97 out of 5 average rating, 116 reviews
Guest favourite
A warm living area features a stone fireplace as the focal point, with a cozy fire burning inside. Comfortable leather seating is arranged around a rustic wooden coffee table, complemented by small decorative items and soft textiles, while glass doors lead to another space.
Cottage in Tiny

Bluestone

Bluestone is located less than 10 minutes' drive from beautiful Awenda Provincial Park in Tiny, Ontario. Every choice was made with guest comfort in mind. In the Summertime, take a short walk down a wooded path to Georgian Bay and perfect swimming, or explore a hiking trail and take in the natural beauty of the area. In Winter, enjoy skiing and snowshoeing locally, or stay in, put a record on, and cozy up by the fire. Licence STRTT-2026-057

4.93 out of 5 average rating, 364 reviews

Popular amenities for cottage rentals in Simcoe County

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Top guest favourite
A wooden deck surrounds a cozy cabin, featuring a shaded barbecue area and two hot tubs. Colorful flower pots add vibrancy, while a large red umbrella provides shade. Lush greenery surrounds the space, enhancing the outdoor setting.
Cottage in Tiny

Private 40 Acre Cottage with Hot Tub

4.97 out of 5 average rating, 320 reviews
Top guest favourite
A spacious hot tub overlooks the Severn River, surrounded by greenery. Chairs are positioned nearby on the grassy lawn, providing a relaxing space to enjoy the water views and sunshine. The calming river scene features boats gently cruising by, enhancing the outdoor experience.
Cottage in Severn Bridge

CARL in Muskoka: Waterfront Cottage with Hot Tub

4.95 out of 5 average rating, 180 reviews
Superhost
The cottage is situated on a well-maintained lawn, framed by trees, with a spacious deck accessible via a stone pathway. Colorful kayaks and a paddle boat are visible by the water, and the sky displays a warm sunset with varying shades of orange and purple.
Cottage in Waubaushene

Waterfront Paradise on the Georgian Bay

4.84 out of 5 average rating, 191 reviews
Superhost
A dining area features a round table surrounded by six white chairs, complemented by a decorative plant. A glass-front cabinet displays glassware. A cozy seating area with a brown couch is visible in the background, accented by a light-colored wall and framed artwork.
Cottage in Midland

House on the Hill, HotTub, Relaxation, Bike Trails

4.85 out of 5 average rating, 267 reviews
Guest favourite
A charming cottage is seen surrounded by trees, with a large deck above. A fire pit is centrally located in the grassy yard, circled by several wooden chairs. A kayak rests nearby, hinting at outdoor activities, while the serene natural setting offers a peaceful retreat.
Cottage in Waubaushene

Charlie the Cottage | Hot Tub | Trail | Hike/Run

4.86 out of 5 average rating, 558 reviews
Top guest favourite
A spacious lake house exterior is set against a cloudy sky, featuring large windows that allow natural light to enter. The surrounding yard is adorned with fallen leaves, while a deck with outdoor furniture and a hot tub enhances the outdoor space.
Cottage in Innisfil

Spacious family cottage 45 mins from GTA!

4.88 out of 5 average rating, 168 reviews
Superhost
Cottage in Innisfil

Tranquil Forest Haven | Hot Tub | 5 Min to Beach

4.84 out of 5 average rating, 439 reviews
Top guest favourite
Cottage in Gravenhurst

Cottage in Gravenhurst

4.96 out of 5 average rating, 274 reviews

Pet-friendly cottage rentals

Top guest favourite
A tranquil lakeside view displays a spacious cottage with large windows, reflecting on the calm water. Surrounding trees and a clear blue sky add to the serene atmosphere, inviting relaxation and enjoyment of the natural beauty.
Cottage in Georgian Bay

Muskoka Stunning Cottage On Little Lake

4.98 out of 5 average rating, 156 reviews
Guest favourite
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

4.92 out of 5 average rating, 209 reviews
Guest favourite
A cozy living area features two armchairs and a comfortable sofa, arranged around a central coffee table. Large windows allow natural light to illuminate the space, showcasing views of the surrounding woods. A television and a stylish lamp enhance the room's functionality.
Cottage in Washago

Relax at The Rock: Muskoka Waterfront Cottage

4.97 out of 5 average rating, 176 reviews
Top guest favourite
Cottage in Innisfil

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

4.86 out of 5 average rating, 271 reviews
Guest favourite
Cottage in Gravenhurst

Marrakahshe Retreat | Luxury Sauna, Beach & Yurt

4.93 out of 5 average rating, 179 reviews
Guest favourite
A charming beach house features a sloped roof and inviting front porch. Steps lead up to the door, flanked by chairs on either side. Large windows allow natural light into the cottage, while sandy grounds create a seamless connection to the surrounding beach.
Cottage in Tiny

Cozy beach house on Georgian Bay

4.88 out of 5 average rating, 147 reviews
Top guest favourite
A wooden dock extends over calm waters, framed by lush forests and rocky shores. Two adirondack chairs face the sunset, inviting a moment of connection. Vibrant hues of orange and purple fill the sky, reflecting gently on the water's surface.
Cottage in Gravenhurst

Private & Modern Muskoka Lakefront Cottage w/ WiFi

4.95 out of 5 average rating, 146 reviews
Top guest favourite
Cottage in Gravenhurst

Where Lake Days Last Longer | Sauna + Beach

4.98 out of 5 average rating, 128 reviews

Private cottage rentals

Top guest favourite
A modern log cottage is viewed from above, featuring a large elevated deck with railings. The structure showcases a combination of dark wood siding and stone accents, with multiple windows allowing natural light. Surrounding greenery adds to the serene environment.
Cottage in Gravenhurst

Foster's Landing - Log Cottage on Lake Muskoka

4.96 out of 5 average rating, 123 reviews
Top guest favourite
A serene waterfront view is presented from a deck, showcasing calm water surrounded by lush green trees. Comfortable seating arrangements are visible, creating a perfect spot for relaxation while enjoying the natural landscape.
Cottage in Torrance

Beautiful Nine Mile Lake

4.97 out of 5 average rating, 258 reviews
Guest favourite
A tranquil lakefront scene at sunset, featuring serene water surrounded by lush trees. Smooth stone terrain leads to the water's edge, where a canoe and a dock are visible. The warm sunlight casts a soft glow across the landscape, creating a peaceful atmosphere.
Cottage in Gravenhurst

Charming Waterfront Cottage - Muskoka - 4 seasons

4.95 out of 5 average rating, 124 reviews
Guest favourite
A spacious common area features a large, light-colored sectional sofa arranged around a warm fireplace built into a stone wall. Large glass doors provide access to a serene outdoor space, while natural light enhances the wood-beamed ceiling. Decorative elements include woven wall art and a wooden side table.
Cottage in Tiny

The Beach House, Georgian Bay, Beach View w/ Sauna

5.0 out of 5 average rating, 18 reviews
Top guest favourite
A charming cottage is nestled along the waterfront, surrounded by colorful autumn foliage. The large wooden deck provides seating and a sunny spot to enjoy the views. A dock extends into the calm water, with kayaks and canoes nearby, inviting outdoor activities.
Cottage in Torrance

Waterfront Cottage in Muskoka | SAUNA | Beach

5.0 out of 5 average rating, 55 reviews
Guest favourite
A spacious two-story home, characterized by a stone façade and large front windows that offer a stunning view of the sunset. The well-maintained lawn is adorned with neatly trimmed shrubs and flowers, leading to a welcoming entryway. The outdoor seating arrangement is visible, suggesting an inviting area for relaxation.
Cottage in Orillia

Lakefront Simcoe Cottage | Dock&Kayaks |Firepit

4.92 out of 5 average rating, 50 reviews
Top guest favourite
A serene outdoor space is featured, illuminated by soft lights under a night sky. A patio area hosts a seating arrangement, surrounded by lush greenery and a fire pit. The water is visible in the background, enhancing the tranquil setting.
Cottage in Beaverton

Private Waterfront Cottage at Lake Simcoe

4.99 out of 5 average rating, 92 reviews
Top guest favourite
An A-frame home is nestled among tall trees, featuring expansive windows that allow natural light to brighten the interior. A spacious deck overlooks the lush greenery, with a stone patio in the foreground, leading to a serene wooded setting.
Cottage in Gravenhurst

Lakefront A-Frame in Muskoka | Sauna & Hot Tub

4.98 out of 5 average rating, 92 reviews

Destinations to explore