Cottage vacation rentals in Simcoe County

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Top-rated cottage rentals in Simcoe County

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A lakeside cottage is surrounded by tall trees, with a gentle slope leading to the water. A private dock is visible, along with several outdoor chairs. The cottage's warm glow is highlighted in the evening light, offering a welcoming appearance.
Cottage in Gravenhurst
4.87 out of 5 average rating, 163 reviews

Waterfront 3 BR Cottage 4 Seasons Gravenhurst Heat

4 Seasons: Heated+A|C! You and friends/family will enjoy easy access to everything Gravenhurst has to offer from our centrally located retreat cottage. Conveniently located on Pine Lake, you will have sun-filled water views throughout the cottage. We are located directly off the main highway, easy road access and parking. The lake is perfect for swimming and water sports. Get ready to sip your morning coffee on the back porch and watch the sun rise! A perfect spot for yoga and/or meditation.

Top guest favorite
An aerial view of a cottage located on a waterfront lot is showcased, framed by lush greenery. A large deck and seating areas are visible, along with a hot tub and sauna. Several boats are docked at the waterfront, indicating access to water activities.
Cottage in Innisfil
4.99 out of 5 average rating, 141 reviews

Charming waterfront cottage on Lake Simcoe

Charming 4 bedroom cottage plus Boat house conveniently located 1 hour from GTA on a private waterfront lot surrounded by mature trees sandy bottom clear water. Proximity of the cottage to the water is sure to please either the sun or shade lovers with multiple large decks dock for sitting dining and lounging. We offer hot tub Sauna basketball net paddle boat floating mat kayaks canoe paddle board pool table, foosball. fishing gear, life jackets. Summertime is by the week, Saturday to Saturday.

Top guest favorite
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
4.97 out of 5 average rating, 126 reviews

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

Top guest favorite
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
4.94 out of 5 average rating, 258 reviews

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!

Guest favorite
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
4.99 out of 5 average rating, 147 reviews

Relax at The Rock: Muskoka Waterfront Cottage

Enjoy fishing, swimming and paddling 22km of the green and black rivers. Paddleboat, canoe, 2 kayaks, and a SUP provided. Take the short 5 minute stroll into town for ice cream or fresh baked treats. Lay out on the elevated deck or in the screened in porch with a good book. End your evening at the riverfront firepit. Nearby day adventures include hiking, golfing, parks, beaches, breweries, casino rama, and downhill skiing at Mount St Louis Moonstone and Horseshoe Valley (30 minute drive).

Guest favorite
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
4.98 out of 5 average rating, 124 reviews

Muskoka Stunning Cottage On Little Lake

Surrounded by Little Lake, this gem provides a relaxing getaway with amazing water views. Spend your days peacefully rowing on the lake or having a picnic on the private beach, and your nights settling by a crackling fire. The home itself is plenty spacious for unwinding and getting a good night's sleep, views all-inclusive. Explore Port Severn Park right next door and play around in the public beach and splash pad. For more adventure, hike the beautiful Georgian Bay Islands National Park.

Top guest favorite
A serene lake view captures twilight colors reflected on the calm surface of the water. Soft pastel hues of pink, purple, and orange fill the sky, while the silhouette of trees frames the horizon, adding to the peaceful ambiance of the lakefront.
Cottage in Georgina
4.99 out of 5 average rating, 168 reviews

Granny's Cottage

Granny’s Cottage is located on Lake Drive East across the road from Lake Simcoe. Our private lakefront is yours to enjoy. Our lakehouse equipped with mini fridge and chairs while looking out over beautiful Lake Simcoe. Lakehouse is available late spring to early fall. This cozy cottage is newly renovated with all the comforts for a much needed getaway. Available for your use is a badminton net, 2 kayaks and a large canoe (seasonal). There is also a secure lock up for you bicycles.

Top guest favorite
A spacious cottage is set against a lush green backdrop, featuring a distinct barrel sauna nearby. A manicured lawn hosts a small putting green with flags, alongside several lounge chairs. The architecture blends modern and natural elements, creating an inviting outdoor environment.
Cottage in Washago
4.96 out of 5 average rating, 112 reviews

Waterfront Cottage sauna/golf/kayaks/beach/games

Welcome to Hally’s Cove Riverside Retreat! A fully loaded 4-season escape on the Trent Severn River! Dock your boat with shore power ⚓, lounge in the over-the-water hammock 🌅, relax in the panoramic sauna 🧖‍♀️, or play in the games room 🕹️ (ping pong, basketball, air hockey plus lots more). Enjoy the 4-hole putting green ⛳, 6 kayaks 🛶, lily pad and custom landscaped Muskoka rock fire pit 🔥. Summer Bonus - Mosquito-sprayed for extra comfort! IG to see more photos: @hallys_cove

Top guest favorite
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
4.97 out of 5 average rating, 237 reviews

Beautiful Nine Mile Lake

Beautiful Muskoka getaway! Modern 4 season waterfront cottage! Stunning views! Located on picturesque Nine Mile Lake. Over 70% of the lake is crown land. Perfect for kayaking and canoeing to enjoy all the beauty Muskoka is known for. We have kayaks a canoe and a paddle board for you to enjoy. Plenty of sun exposure on the dock you can swim all day long. Close to hiking and snowmobile trails. May 15-Oct Minimum 6 nights with a Sunday check in.

Guest favorite
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
4.94 out of 5 average rating, 304 reviews

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. License #STRTT-2025-008

Guest favorite
Cottage in Innisfil
4.84 out of 5 average rating, 241 reviews

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

Escape the city and unwind at our charming three-bedroom bungalow on Lake Simcoe, just one hour north of Toronto. With 129 feet of private lakefront, you’ll wake up to breathtaking sunrises and stunning water views, making it the perfect all-season getaway. 🌅 Unmatched Lakefront Views 🏖️ Private & Peaceful 🏊 Shallow, Swimmable Waters 🏞️ Spacious Outdoor Area 🎣 Cozy Year-Round Escape 🚗 Easy Access – Just a one-hour drive from Toronto

Guest favorite
An aerial view captures a waterfront community at sunset, featuring modern buildings along the marina. Boats are docked at the waterfront, and a serene lake reflects the warm colors of the sky. Lush greenery lines the horizon, adding a sense of tranquility.
Cottage in Innisfil
4.88 out of 5 average rating, 329 reviews

Boardwalk Bliss For Two *1 hr From TO!*

Waterfront Escape – 1 Hour from Toronto! Enjoy a private, street-level retreat steps from the marina boardwalk! Perfect for a relaxing getaway or remote work, with fast WiFi and in-room entertainment. 🌊 Activities Nearby: Waterside Dining & Boardwalk Music Nature Trails, Golf & Spa 🚤 Optional Add-Ons: ✔ Boating Excursions (Pre-Book) ✔ Dining & Activity Combos 📆 Book Now – Dates Fill Fast!

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