Cottage vacation rentals in Simcoe County

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Top-rated cottage rentals in Simcoe County

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Guest favorite

Cottage in Wasaga Beach

4.96 out of 5 average rating, 135 reviews

Sanablue by the Bay -Stylishly Untrendy since 1958

Sanablue is a quiet out of the way escape for your family ... that's right next to everything that's great about Wasaga! Extra clean & sanitized. See reviews for our track record! Just 91 barefoot steps to the edge of Georgian Bay (yep, an 11 year old paced them of for us!). A 4 min stroll to grab a coffee (or a bottle of wine). Just meters to Oakview Woods hiking trails & Wasaga biking trails. 10 min to Collingwood. 15 min to breathtaking Blue Mountain ..... Or just put your feet up & relax.

May 28 – Jun 4

G$28,951 GYD per night

Guest favorite

Cottage in Tiny

4.94 out of 5 average rating, 118 reviews

Cozy 4 Season Family Cottage

***NEW LISTING*** 4 season cottage, 5 min walk to beaches. Approx 1300sq. feet including 3 bedrooms and 1 large bathroom. Accommodates 6-8 Comfortably. Large Wrap around deck with outdoor furniture and greenery provided and BBQ Area to keep you relaxed and at home. Outdoor fire pit available. Situated on a private lot surrounded by nature. This getaway is equipped with everything you need - appliances and utensils, linens, Wifi, TV, board games, laundry with plenty more to do in the area.

Sep 20 – 27

G$35,247 GYD per night

Superhost

Cottage in Waubaushene

4.81 out of 5 average rating, 126 reviews

The Cottage on Coldwater; where bay & trail meet.

Georgian Bay on one side and the Tay Trail on the other, this lakeside cottage offers gifts for all seasons. With spectacular views of the bay ready 4 ice fishing, sledding, skiing and snow shoeing over winter; hiking, biking, boating and swimming over summer with infinite possibilities in between, we're sure Waubaushene will suit your needs. Close to quaint Coldwater stores, kilometers of Parks, a short drive to 2 ski hills and just off Hwy 400, this hidden gem can accommodate adventure.

May 7 – 14

G$27,711 GYD per night

Guest favorite

Cottage in Georgina

4.98 out of 5 average rating, 132 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.

Oct 14 – 21

G$35,371 GYD per night

Guest favorite

Cottage in Wasaga Beach

4.89 out of 5 average rating, 205 reviews

Cozy Riverfront Cottage Retreat with Dock / Ski

→Bright, 2 bedroom cottage with 1 queen, 1 twin bunk bed and 1 cot →Comfortably sleeps up to five →Ideal for families, couples →Fantastic views up and down the Nottawasaga River →Central to skiing - Blue Mountain, Mount St Louis Moonstone, Horseshoe →9 Minutes to the NEW Wasaga Beach Casino →Great fishing (Steelhead, trout, pike, salmon, bass, pickerel), boating, canoeing, kayaking →Large Dock on the Nottawasaga river →On-premise parking for up to 3 vehicles →High-Speed unlimited internet

Jun 22 – 29

G$67,506 GYD per night

Superhost

Cottage in Innisfil

4.83 out of 5 average rating, 241 reviews

Cozy cottage nestled in the forest, near the beach

Beautiful, modern, cottage-like home nestled in the trees. Located on a large and extremely private property at the end of a small gravel road with no neighbours on one side. Huge yard backs onto a forest with trails leaving your doorstep. Mapleview beach is only a short walk to the bottom of the road and there are so many other scenic beaches in the Sandy Cove area. The home is fully equipped, clean and cozy, with high speed internet and smart TVs, comfy bedding and pillowtop mattress.

May 7 – 14

G$27,133 GYD per night

Guest favorite

Cottage in Innisfil

4.94 out of 5 average rating, 151 reviews

Utopia Villa and Spa

Welcome to Utopia where you will make amazing long lasting memories with your family and friends. Just minutes from the beach, grocery stores, gas stations, and anything else you can need. There is so much to do here that you will never want to leave! Imagine a day full of good food by the fireplace, a dip in the hot tub, relaxing in the sauna and playing in the game room. Treat yourself with a stay! House rule: No smoking/eating in hot tub. Breaking this rule will result in $500 fine.

Sep 16 – 23

G$63,498 GYD per night

Guest favorite

Cottage in Innisfil

4.91 out of 5 average rating, 128 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 🤫 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, all high tech.

Oct 26 – Nov 2

G$74,799 GYD per night

Guest favorite

Cottage in Port McNicoll

4.98 out of 5 average rating, 125 reviews

Boe's Cottage: Newly Renovated - Great WIFI

Experience Southern Georgian Bay - Ontario's Four Season Playground. Just 90 Minutes from Toronto! Relax in our fully renovated 4 season cabin with all the amenities of home. Steps from the lake with parks, beaches, hiking, kayaking. And in the winter, snowshoe, skate, snowmobile, cross country & downhill skiing at Mount st. louis moonstone Great setup for a 'working' vacation with excellent WIFI 10 Minutes to Midland for restaurants & unique shopping experiences

Nov 6 – 13

G$22,567 GYD per night

Guest favorite

Cottage in Torrance

4.97 out of 5 average rating, 194 reviews

Beautiful Nine Mile Lake

Beautiful Muskoka getaway! Newly renovated 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 2 Minimum 6 nights with a Sunday check in.

May 20 – 25

G$35,042 GYD per night

Guest favorite

Cottage in Tiny

4.94 out of 5 average rating, 206 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-2024-017

Nov 29 – Dec 6

G$37,282 GYD per night

Superhost

Cottage in Port Severn

4.86 out of 5 average rating, 130 reviews

Cottage "Down By The Bay"

1 bdrm cottage in beautiful Port Severn, ON with firepit, WIFI, Heat and AC. Great location year round. Located on the main road into Honey Harbour, ON and close to amenities such as Tim Hortens, LCBO, gas stations and restaurants. Near water and beaches (NOT A WATERFRONT- Port Severn Park and Beach is 7 min drive) Right beside entrance to OFSC trails for snowmobiling Mount ST. Louis is a 20 min drive Fishing/ice fishing options nearby

Jan 7 – 14

G$18,549 GYD per night