Cottage vacation rentals in Midland

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Top-rated cottage rentals in Midland

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Guest favorite

Cottage in Tiny

4.96 out of 5 average rating, 109 reviews

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

Jun 6 – 13

€ 341 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 30 – Oct 7

€ 169 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.

Jun 11 – 18

€ 146 per night

Guest favorite

Cottage in Torrance

4.97 out of 5 average rating, 118 reviews

The Lantern Cottage - Lake Muskoka

This Muskoka cottage is a perfect getaway. It has a stylish, clean, airy decor. Small hot tub off the back deck. Good distance from neighbours for privacy. Suitable for couples, small families (max 5 people). Situated 60 m from Lake Muskoka with direct access to public dock, boat launch, sunset views, and fishing. Water access is a one minute stroll to the dock. Cottage has a partial view of the lake from the cottage porch. Primary guest must be a responsible adult based on reviews.

Mar 25 – Apr 1

€ 191 per night

Guest favorite

Cottage in Bracebridge

4.9 out of 5 average rating, 438 reviews

Cottage on the Muskoka River

The cottage has a nice private setting as part of a parcel of land which is almost 20 acres along the Muskoka River, close to 3 waterfalls and on the Trans Canada Trail. You’ll love our place because of the access to many trails for hiking, yet only a few minutes to downtown Bracebridge and central to most Muskoka Attractions. To really enjoy the river location you need to love walking and exploring. The cottage is offered in its pre-renovation state as the pictures indicate.

Jan 10 – 17

€ 126 per night

Guest favorite

Cottage in Bala

4.94 out of 5 average rating, 125 reviews

Charming Lakefront Bala Cottage

This charming, cozy, 4 season cottage overlooks the Moon River in the heart of Bala, just 12 minutes off the 400! With over a half-acre of land, this gem is located within minutes to the grocery store, Don’s Bakery, Beer Store, LCBO, The Kee, markets, hiking trails, snowmobile trails & more. 2 minutes to Bala (15 min walk) 10 minutes to Port Carling 15 minutes to Gravenhurst 25 minutes to Bracebridge Cottage is fully equipped for you to enjoy, just bring your personal items!

Dec 10 – 17

€ 163 per night

Superhost

Cottage in Waubaushene

4.86 out of 5 average rating, 396 reviews

Modern Cottage w/ Hot Tub on 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.

Jul 2 – 9

€ 470 per night

Guest favorite

Cottage in Port Carling

4.99 out of 5 average rating, 122 reviews

Lake Muskoka Classic Cottage w/ Hot Tub

Start planning your retreat at this four season luxury private residence on lake Muskoka. Located in the heart of Muskoka’s pristine natural beauty. Relax and enjoy a truly unforgettable experience from the moment you arrive and create life long memories with loved ones. Home features a chef kitchen, butlers pantry, cozy double sided wood burning fireplace, heated floors in bathrooms, wrap around balcony, complete privacy from neighbours. Additional services available.

Mar 8 – 15

€ 721 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

Jan 5 – 12

€ 130 per night

Guest favorite

Cottage in Torrance

4.97 out of 5 average rating, 195 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

€ 159 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

Apr 13 – 20

€ 176 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 31 – Feb 7

€ 95 per night