Cottage holiday rentals in Midland

Summer Getaway - 3 min walk to Beach, Clean & Cozy

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

Waterfront Paradise on the Georgian Bay

This beautiful cottage of 2950sqft faces a breathtaking view of the Georgian Bay with over 105ft of lakefront. During the summer, this cottage is perfect for ATV and bike trails, wateractivities and fishing. The cottage includes kayaks and a paddle boat for the guests to enjoy. During the winter, the cottage is ideal for ice fishing and is only a 13 minute drive to Mount St. Louis skiing. Under 10 minute driving distance to beaches, Tim Horton’s, LCBO, gas station, ice cream parlour and more.

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.

Victoria Harbour Cottages 2 Bedroom Cottage

Comfortable and spacious fully equipped 2 bedroom waterfront cottage for your summer or winter getaway! Excellent location- only 1hr & 1/2 from the GTA. Minutes from Victoria Harbour, just outside of Midland. Enjoy the convenience of nearby shops, groceries, LCBO, and restaurants while overlooking the beauty of the southern shores of Georgian Bay! Truly the best of both worlds! Nearby attractions include Sainte Marie Among the Hurons, Martyr’s Shrine, Wye Marsh, Tay Trail, Golf, and skiing.

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

Modern cottage with sunset views of Georgian Bay right on the paved Tay Shore Trail for running/biking/snowshoeing. Newly renovated from top to bottom! Enjoy the 500 sqft deck with year round Hot Tub, BBQ and patio table. Fire pit in the backyard. The house is on a large lot surrounded by evergreens for privacy. Across the trail you can access the water, 5 min walk to a sandy beach. 1.5hrs from Toronto, 30mins north of Barrie, 12mins to Mt St Louis Moonstone for skiing.

Stunning Waterfront Cottage & Bunkie!

Beautiful 2-bedroom Cottage plus 1-bedroom Bunkie on Georgian Bay! Located in a quiet area with a private beach! In the summer the lake is perfect for swimming! Just bring water shoes as there can be rocks and zebra muscles. We have a two-person kayak, perfect for a day out on the water. In the evening, curl up by the outdoor fire pit, roast marshmallows and enjoy the amazing sunsets! It is the perfect place for a summer getaway! Please note this cottage is Pet Free.

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.

Georgian Bay Cottage-HotTub/Sauna/Swim/Hike/Marina

*** MIN 3 NIGHTS STAY DURING LONG WEEKENDS HOLIDAYS, AND IN THE SUMMER*** Pack up the car and escape the city for a relaxing outdoors. Kayaking on a lake, swimming at the beach, laying in a hammock, grilling burgers, and making s'mores by the fire are among the many fun activities to enjoy at my cottage. Georgian Bay Retreat is an exclusive destination for families with kids or mature couples looking for an amazing time together, very close to the water.

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

Muskoka Waterfront Cabin w/ pool table&Falls view

Welcome to Fallsview Dream cottage! Enjoy the property’s STUNNING waterfront, hot tub, pool table & private beach This cozy cabin is perfect for those who love nature, privacy and the cottage life. Right in the middle of the woods with the most beautiful waterfall view. Watch the sunrise and sunset right from the deck surrounded by trees. Take the time to reconnect with your family/friends :)

Private 40 Acre Cottage with Hot Tub

Our two bedroom cabin + cubby (available in summers) by a scenic pond is a private getaway while close to the main road and many amenities. Private outdoor space includes hot tub, deck, fire pit, and walking trails. We have a barn with ping pong and foosball tables. We are 20 min to Barrie, 10 min to Midland, 20 min to Balm beach, Wasaga beach, Mt. St Louis and Horseshoe Valley resort.

Cozy Beach Cottage with Pool | Georgian Bay

Georgian Bay Beach club. Cute cottage perfect for families, couples, or anyone wanting to relax! 2 bedrooms, 1 bathroom, furnished, pool and private beach on the shores of beautiful Georgian Bay in Tiny township. Cottage is part of a 12 cottage community that shares the pool and beach area. Always super clean, professionally cleaned after every guest! Note: pool is closed October to mid May.