Cottage vacation rentals in Midland

Georgian Bay Waterfront Cottage HotTub King Bed

Escape to this exceptional modern Lake house on Georgian Bay shores. Enjoy Incredible sunsets and views while you unwind in the hot tub or around the fire. Use the Kayaks to explore the Georgian Bay shores. This home can accommodate up to 4 adult guests (one additional child) Our quite property is best suited for 1 to 2 couples or a family of 5 or less and is fully equipped so you can relax on your next summer or winter getaway. Add the waterfront Bunkie to your summer stay (see additional fee)

Family · Location · Getting around

Forest Oasis in Tay w/Large Jacuzzi Hottub

Beautiful cottage situated on the most southern point of Georgian Bay in Victoria Harbour. Less then 2 hours from the GTA with full amenities including an LCBO and Foodland 5 minutes away. Take advantage of plenty outdoor activities. Enjoy a bike ride on the stunning Tay Shore Trail, swimming in the lake on a hot summer day or hit the local slopes at Mt St Louie during the winter. Regardless of your choice in activities, end the evening with a soak in the hottub. Don't forget to look for stars!

Family · Location · Amenities

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

Location · Value · TV

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 board 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.

Location · Value · Check-in

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.

Value · Family · Wifi

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.

Location · Value · Pets

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.

Location · Value · Access

Tiny Luxury Cottage with Hot Tub

This tiny luxury 2 bedroom cottage is perfect for a romantic couple or small family getaway. Nestled on 1.5 acres among majestic trees and granite outcrops, creates beautiful views from the deck with BBQ, fire pit, hot tub or massive windows throughout the cottage. Water dam and river across the road create relaxing waterfall sounds that are heard from deck or enjoy it close up from the private shoreline deck and dock. Explore the Muskoka River on the kayak, SUP or river tubes.

Value · Location · Layout

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.

Value · Location · Quiet

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.

Location · Value · View

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.

Family · Value · Indoor spaces

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

Family · Location · Sleep quality