Cottage holiday rentals in Oro-Medonte

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

Cozy Winter Wonderland Escape with Hot Tub

Beautiful, modern, pet-friendly cottage nestled in the trees. Located on a large, private lot secluded at the end of a small gravel road. The huge yard backs onto a forest with an extensive trail network meandering a peaceful river steps from your backdoor. Mapleview beach is a short walk down the road along with many other scenic beaches in the area. The cottage is warm, cozy and fully equipped. Offering high-speed internet and smart TVs, brand new hot tub, BBQ, outdoor firepit, and boardgames.

Waterfront Cottage-Sauna, Dock, 4-bed, 4 Parking

Bright and airy waterfront cottage in one of Lake Simcoe’s most desirable areas. The open-concept layout and unique lot design offer stunning lake views from almost every room. Enjoy custom furnishings, stylish decor, and a fully equipped kitchen—perfect for relaxing getaways or extended stays. Whether you're here for a peaceful retreat or lakeside fun, this cottage provides comfort, beauty, and convenience in a serene upscale setting. Ask us about fun activities that Lake Simcoe offers.

Cozy Winter Escape - Ski, Hike & Chill by the fire

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

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.

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).

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.

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.

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.

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

GATED RESORT COTTAGE

[CLICK SHOW MORE FOR IMPORTANT INFO] Sought-after cottage located in the gated Wasaga Country Life resort; professionally managed year-round by Parkbridge. A short walk from the beach with full access to resort amenities including; indoor/outdoor swimming pools, private trails, playgrounds, mini golf, sports fields and many more professionally managed facilities. View the "Where you'll be" section below for a full list of amenities.

Spacious Cottage Escape with Lakeside Hot Tub

Escape from the usual! Bring your crew to our spacious 5 bdrm, 2 washroom, Lake Front cottage and RELAX. Enjoy the warmth of the fireplace and the beautiful view from the sunroom. Soak in the hot tub and watch the sunset. Proximity to Orillia's shops and restaurants. Casino Rama is 2km away for a completely different kind of fun. Two adult Kayaks available in spring and fall. Hot tub and bbq year round.