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Holiday rentals in The Mountain

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Top-rated holiday rentals in The Mountain

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A spacious living area is highlighted by a large white stone fireplace, surrounded by comfortable seating. Natural light filters through sheer curtains, enhancing the warm atmosphere. A flat-screen television is mounted above the fireplace, and a wooden dining table sits elegantly in the foreground.
Cottage in Tiny
4.97 out of 5 average rating, 128 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

Top guest favourite
The historic Beck House, a striking Victorian structure, stands with a distinctive red façade and slate roof. A spacious porch with white railings invites guests, while the well-kept lawn adds to its charm. A wooden sign identifies the property, blending history with a warm welcome.
Flat in Penetanguishene
4.89 out of 5 average rating, 524 reviews

The Haunted House Apt 302

As you pull into the driveway this 1885 Victorian towers above you, your mouth drops in awe of the size. Up the porch to enter a small front door, a dimly lit winding staircase creaks as you ascend to 3rd floor. Original architecture painted many times over oozes with history. 70 years ago the house was turned into apartments, unloved for many of those years, time has definately taken its tole, yet to the spirits within, their big old house still stands proud and distinguished in all its glory.

Guest favourite
A spacious outdoor balcony features a wooden deck with a green and white patterned rug. Two chairs are positioned around a glass-top table, surrounded by lush greenery from neighboring trees. A large window on the wall offers natural light to the space.
Flat in Midland
4.9 out of 5 average rating, 130 reviews

Loft By The Bay

Welcome to our charming second storey apartment in downtown Midland, Ontario. This cozy space features a bedroom, office with futon, full kitchen, bathroom, laundry, and a bright open concept living area. Enjoy easy access to local shops, restaurants, and attractions. Explore the picturesque waterfront and nearby hiking trails. Retreat to this comfortable and inviting apartment after a day of work or play. Book your stay today for a convenient, comfortable, and memorable experience in Midland.

Top guest favourite
Cottage in Victoria Harbour
4.83 out of 5 average rating, 233 reviews

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.

Guest favourite
A covered deck features white patio furniture, including a circular table and several chairs, overlooking serene Georgian Bay. Soft lighting is provided by hanging glass pendant lights. The sandy beach is visible below, with gentle waves lapping at the shore under a partly cloudy sky.
Cottage in Tiny
4.97 out of 5 average rating, 149 reviews

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.

Top guest favourite
A rustic wooden dining table is set with plates and jars of milk, complementing a cozy gas stove. Large windows frame views of the bay and surrounding nature, while soft curtains allow natural light to fill the room.
Tiny home in Waubaushene
5 out of 5 average rating, 240 reviews

Saltbox by the Bay + Snowshoes/Ski/Snowboard/Vetta

JANUARY AVAILS + Snowshoes + Skiing Welcome to Saltbox by the Bay, your 4-season escape. Perfect for couples, a small family/friends getaway or solo retreat. This vintage cottage is upcycled with luxe amenities. Made for slow living, play boardgames & classic albums & watch sunsets over the bay. Explore winter in cottage country: borrow our snowshoes for a trek, visit Quayle's Brewery, pamper yourself at Vetta Nordic Spa, ski/snowboard Mount St. Louis or head into town for dinner & bowling.

Top guest favourite
A charming two-story house is captured against a clear blue sky. The exterior features horizontal grey siding, wooden accents, and a balcony above the entrance. A stone facade frames the lower part of the structure, while a garage door adds to the home's appeal.
Flat in Penetanguishene
4.99 out of 5 average rating, 102 reviews

By The Bay spacious one bedroom

This unique place has a style all its own and only steps away from , beaches , water front dining and theater! With all the amenities of home you'll be comfortable to stay for the weekend or extended stays. Fully equipped kitchen with convection oven , dishwasher , microwave, keurig coffee maker and built in washer/ dryer . Spacious bathroom with an over sized walk in shower . And to end the day enjoy the full sized bed room and closet to unpack luggage with a queen size Endy foam mattress .

Top guest favourite
Two wooden Adirondack chairs are positioned on a lush green lawn facing the water, framed by overhanging tree branches. The sunset creates a colorful display on the horizon, reflecting on the calm surface of the lake, while a small table holds a wine bottle and glasses.
Guest house in Victoria Harbour
4.96 out of 5 average rating, 284 reviews

Sunset Beach Cottage

Part log treehouse, part beach house and 100% of what you need to enjoy a peaceful getaway only 1.5 hours from Toronto! Walk up the private staircase and pause to enjoy the spectacular treetop and waterfront views from your own wraparound deck before entering your 900 sq. ft. oasis. Enjoy access to your own lawn, picnic table and beach* area and all that Georgian Bay and the area has to offer. *water levels fluctuate Insta: sunset_beach_cottage_canada

Guest favourite
A modern garage apartment is displayed, featuring a neutral-toned exterior with a large garage door and a side entrance. A spacious driveway is visible, providing ample parking space. The entrance is highlighted by a white door, and trees are partially visible in the background.
Flat in Midland
4.94 out of 5 average rating, 179 reviews

Hosted by Nous Midland

Small-town charm at its best! Our centrally located apartment is the perfect home base for your small-town adventures. We're minutes from the unique shops and restaurants in downtown Midland and the Midland Harbour. There is plenty to experience; attend a local festival, take in a tourism site, hop onto the Trans Canada Trail System with your bike or snowmobile, attend a show/concert at the Midland Cultural Centre, or snowshoe through the Wye Marsh.

Guest favourite
A cozy outdoor fire pit area is designed with smooth stones surrounding a crackling fire. Two black wooden chairs provide seating nearby. In the background, a cottage features string lights and large windows, nestled among trees in a serene garden setting.
Cottage in Tiny
4.93 out of 5 average rating, 336 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. Licence STRTT-2026-057

Guest favourite
Loft in Midland
4.89 out of 5 average rating, 396 reviews

Nest By The Bay - Downtown Midland / Private Loft

Luxury, Comfort & Style. This one-of-a-kind rental, "Nest By The Bay", is located in Downtown Midland. Walk everywhere, park your car & enjoy what Midland has to offer. Midland Harbour is only minutes by foot. Live our lifestyle, enjoy our many festivals, professional theatre, artisans, culinary cuisine, seasonal events & so much more! See our other listing "Perch By The Bay", also at this same location. Listing not suitable for ages under 6.

Guest favourite
Cottage in Lafontaine
4.84 out of 5 average rating, 271 reviews

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.

Popular amenities for The Mountain holiday rentals

  1. Airbnb
  2. Canada
  3. Ontario
  4. Simcoe County
  5. Midland
  6. The Mountain