House vacation rentals in Midland

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Top-rated house rentals in Midland

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Guest favorite

An A-frame house featuring a white exterior and a steep roof stands beside a serene lake. A gravel driveway leads to the entrance, surrounded by greenery. Large windows allow ample natural light, providing views of the lake and trees in the background.

Home in Little Lake

4.88 out of 5 average rating, 106 reviews

Lakefront detached house on the little lake

♥️an unique, lovely elf house in front of the little lake. Here you’ll find a unique hideaway in the middle of the city Barrie with gorgeous lake views as far as the eye can see. ♥️ Only one hour drive from Toronto. Walking distance to everywhere (shoppers,restaurants, cinemas….) ♥️This home including new furniture, microwave, coffee maker, washing machine and all other appliances ! Walk out the back door and be greeted by our updated dock where you can fish for pike, perch, pickerel and bass.

Guest favorite

A charming entrance features a dark wooden door adorned with a seasonal wreath. Flanking the door are planted chrysanthemums in varied colors. A wicker bench and a blue Adirondack chair are positioned on the spacious deck, alongside pumpkins adding a festive touch.

Home in Gravenhurst

4.97 out of 5 average rating, 105 reviews

Sawdust city haus

Bringing it back to our roots. This 800 sq/ft home from the 50’s has undergone major renovations with you in mind. Located steps from Lake Muskoka, a short drive to the Gravenhurst wharf, an even shorter drive to town & Dr Bethune; just the beginning of what this home has to offer. Enjoy walking trails, a boat launch with private mooring space, sawdust city brewery, the oar restaurant, Muskoka boat rentals, steamship tours, parasailing, local events, etc. all from the privacy of a dead end road.

Guest favorite

A private swimming pool is surrounded by well-maintained gardens, featuring vibrant green shrubs and flowers. A spacious patio area with outdoor furniture is also visible. The clear blue sky enhances the serene ambiance of this inviting outdoor space.

Home in Midland

4.8 out of 5 average rating, 45 reviews

Our vacation home. Fully equipped. Pool. Fire Pit.

Stylish. Privacy. Location. Our Vacation Home, is in vibrant Downtown Midland. We’ve recently renovated our amazing century home and it is ready for you to enjoy! – its beauty matches the beauty of the town. Our spacious home features a great backyard for you to relax in. When venturing out to explore the area we know you’ll enjoy Midland Harbour. This picturesque natural attraction has been a favourite of tourists and boaters from around the world. Our home is just a few minutes’ walk away!

Top guest favorite

A welcoming entrance features a decorative front door with intricate design flanked by large windows. A well-maintained garden with colorful flowers, including marigolds, enhances the space, while a manicured lawn provides a vibrant green backdrop.

Home in Penetanguishene

4.97 out of 5 average rating, 159 reviews

White Rolling Sands of Penetang by Theatre

Shores of Georgian Bay - enjoy a firepit in the backyard of a deep lot backing onto woods with trails. Local walking and cycling routes, vege and flower gardens from private sunny back deck. Fully licensed and located close to Kings' Wharf Theatre / Discovery Harbour. Experience the natural beauty of Tiny Beaches, Georgian Bay Islands N.P and Awenda P.P. nearby (Park pass available for use). Marinas, beaches, boat cruise of the islands, Ste Marie Among the Hurons and Wye Marsh (Midland) nearby.

Top guest favorite

A bright living area features large windows that offer views of the surrounding woods. Soft seating options are arranged around a neutral rug, with a central fireplace enhancing the cozy setting. A dining table is visible in the background, accompanied by decorative artwork on the walls.

Home in Tiny

5 out of 5 average rating, 43 reviews

Tiny Beaches Getaway

Kick back and relax in this calm, stylish space. Nestled in a quiet neighbourhood only 9 minutes walking distance from one of the nicest sandy beaches ( Ossassane Beach) on Georgian Bay this Adult Retreat is a perfect getaway from the busy city life . Enjoy the turquoise waters ( you will think your are somewhere in Carribean) of Georgian Bay during the day and gather around the firepit out back on cozy summer nights to enjoy good conversation and drink in privacy surrounded by woods .

Guest favorite

The exterior of The Lookout reveals a modern cottage design with light wood accents and a welcoming porch. Large windows showcase the surrounding trees, and the cozy yard offers a glimpse of seasonal foliage.

Home in Tiny

4.96 out of 5 average rating, 23 reviews

Luxury Cottage - The Lookout. Next to Balm Beach

Welcome to The Lookout, hosted by The Cawaja General Store! This cozy, 2-bedroom modern cottage is just a short stroll from beautiful Balm Beach on Georgian Bay. Designed with comfort in mind, it offers a private sauna, fire pit, heated bathroom floors, plush towels, eco-friendly soaps, and a fully equipped chef’s kitchen. Enjoy a spacious living room with a warm gas fireplace, HD TV, Wi-Fi, a variety of board games, and a handpicked book library. Every detail invites you to unwind and relax!

Top guest favorite

The large bedroom features a queen canopy bed with detailed linens. A decorative rug in warm tones complements the wooden furniture. Natural light filters through the window blinds, and a chair is situated in one corner, adding comfort to the space.

Home in Midland

5 out of 5 average rating, 71 reviews

Historic Coach House hosted by John & Donna

Approx. 600 sq ft of living space. 2 guests. 1 large bedroom with queen canopy bed - includes linens. 1 bath with original claw tub and shower - includes soap, toilet paper, towels. Great location on historic street. Kitchen - fridge, stove, dishwasher, coffee maker, toaster Dining room with antique table and chairs. Sitting room. Free parking for 1 car on premises. Air conditioning and heating. Wi-Fi. Private entrance. Large deck. Minimum stay 2 nights. Please no pets. No smoking or vaping.

Guest favorite

The charming log cabin is surrounded by trees, featuring a spacious deck with pink seating and a covered outdoor area. A hot tub and manicured lawn add to the inviting outdoor space. Large windows reveal the warm wood interior and capture natural light.

Home in Bracebridge

4.94 out of 5 average rating, 397 reviews

Muskoka Hideaway-hot tub/private trails/wood stove

Hidden amongst the trees in the middle of Muskoka, this Hemlock log cabin boasts high ceilings and a true "cabin in the woods" feel. Its not hard to relax and unwind with a coffee in front of the fire, or go and explore along the private forest trails (1-2k of walking trails). As well, downtown Bracebridge is a convenient 10 minute drive away with all amenities. There is a veggie garden on the property and depending when you come you can pick away at it :) Pets are welcome in the home!

Superhost

A stone pathway leads to a fire pit surrounded by colorful Adirondack chairs in red and yellow. The view overlooks the lake, with a dock extending into the water under a clear blue sky, providing a serene setting for gatherings.

Home in Orillia

4.82 out of 5 average rating, 259 reviews

Waterfront Cottage Over-the-Water view w fast Wifi

Our cottage backs directly onto lake Simcoe with a view overlooking the water reminiscent of a four season water villa bungalow. Enjoy the entire house with your family and friends and be captivated by nature's beauty as the sun sets behind the treeline across the lake. Easy access to lake Couchiching for fishing in the summer and ice fishing in the winter, 30 mins to Mount St. Louis for skiing and snowboarding, 30 mins to Vetta Nordic Spa and Casino Rama is only a 10 minute drive away!

Guest favorite

An inviting living area is highlighted by a cozy fireplace with a flickering flame. A mounted TV is positioned above a shelf containing various movies. Soft seating arrangements are present, complemented by a decorative sign and a window that lets in natural light.

Home in Tiny

4.87 out of 5 average rating, 129 reviews

Beachy Blue Bay Cottage - licence #STRTT-2025-194

A 2 min walk to the beach, this 4 bedroom Cottage with Circular Driveway is bright and newly renovated with an open concept main floor. Very private and surrounded by mature trees. Relax on a very large deck with gas BBQ, seating and patio table. Over looking the deck is the fire pit area with lots of room for the kids to play & roast s’mores. The basement is well equipped with pool table, dart board, air-hockey, kids toys, board games & a small TV with lots of movies to snuggle up to!

Guest favorite

A spacious living area features large windows that provide ample natural light and views of the surrounding trees and water. A comfortable sectional sofa, a stylish leather couch, and a glass coffee table are arranged around a cozy wood stove, creating a welcoming atmosphere.

Home in Port Carling

4.91 out of 5 average rating, 119 reviews

Waterfront Boutique Cottage Getaway

Welcome to your cozy and relaxing cottage getaway in Muskoka. Situated on the serene waters of Bass Lake, explore the nearby town of Port Carling - known for its Snowmobiling Trails, Charming Shops, Restaurants, and stunning Lakeside View. A short walk to Bass Lake Roadhouse Restaurant. This home is surrounded by lush trees and stunning views of the water, it is the perfect blend of rustic charm and modern amenities to make your stay comfortable and enjoyable all year round.

Superhost

A spacious living room features a large sectional couch and a round coffee table. Natural light floods the space through multiple windows, illuminating a cozy bay window seating area. A decorative plant and a mounted flat-screen TV add to the welcoming ambiance.

Home in Barrie

4.86 out of 5 average rating, 117 reviews

King Bed Farmhouse- w/ Fire-pit, 75" TV, Ping Pong

Great location- 7 min to Waterfront, 18 min to Horseshoe Resort and Snow Valley Ski Resort, 18 min to Vetta Spa. Entire Private and Cozy 4 Bedroom 2 bath Home - Fully Equipped Kitchen! - Media Room w/ 75" Smart TV, Ping Pong & Foosball table!! - Outdoor Patio with Fire-pit area! - Fast Wifi and Parking for 4 Cars!! - 5 Beds and a Sofa Bed. - Park Across the Street... - Comfy Bay Window Seating!!