Vacation rentals in Wyebridge

4.84 out of 5 average rating, 249 reviews

A modern kitchen area features sleek white cabinets and wooden countertops. A round rug lies beneath a wooden dining table with black chairs, creating a cozy dining space. Natural light fills the room through the large windows, showcasing greenery outside.

Guest suite in Moonstone

RELAX @ our HOT TUB and SAUNA in the woods

PLEASE READ! Mt. St. Louis & Horseshoe Valley at doorstep! This is a bright, large and private walk-out GUEST SUITE (basement apartment). Hot tub, patio, fire pit & secluded path in the woods to enjoy nature. Kitchen is equipped with an induction cooktop and all things necessary, even wine bottle opener:) Open concept living room/kitchen/dining room with TV & Roku. Bedroom is a work of Art: dark, mysterious and romantic! Custom Queen bed made from weathered barn wood salvaged from our property.

4.87 out of 5 average rating, 411 reviews

A waterfront patio features a dock extending into Georgian Bay, accompanied by several lounge chairs arranged for relaxation. An umbrella provides shade, enhancing the scenic view of the calm water and distant shore under a clear sky.

Home in Meaford

Waterfront* Hot Tub* - Beachhouse Hideaway *Unique

This beach house was designed with relaxation and the enjoyment of togetherness in mind. Let your worries melt away as you slip into the warmth of this water side hot tub featuring stunning view across Georgian Bay and up the mountain side, as fresh snow falls around you. The open concept design makes this the perfect place to gather with family and friends w/ walkout waterfront patio and dock access for swimming. 2 min to downtown Meaford, 20 min to Blue Mtn, 1.5 hrs to Tobermory. Hiking Trails

5 out of 5 average rating, 183 reviews

Tiny home in Waubaushene

Saltbox by the Bay | Vetta/Tay Shore Trail/Bikes

*GUEST BIKES AVAILABLE* Welcome to Saltbox by the Bay, your 4-season escape. A perfect couple's getaway or small family, friends or solo retreat. This vintage cottage is upcycled with luxe amenities. Make delicious meals, play records & boardgames & watch sunsets over the bay. Explore the treats of cottage country: walk or bike the Tay Shore Trail, visit Quayle's Brewery & Wye Marsh, pamper yourself at Vetta Nordic Spa & enjoy one of the nearby towns for beaches, restaurants & local amenities.

A serene beach scene is displayed, featuring soft sand and gentle waves lapping at the shore. The sky is painted with wispy clouds and blue hues, while the horizon stretches into the calm water, inviting relaxation and outdoor exploration.

4.97 out of 5 average rating, 120 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

Apartment in Penetanguishene

The historic Beck House is depicted in this image, showcasing its striking red facade and unique architectural features. A white porch with hanging plants can be seen on the front. The surrounding greenery adds to the charm of the property.

4.92 out of 5 average rating, 253 reviews

The Haunted House Apt 301

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.

Cottage in Victoria Harbour

A rustic kitchen space features a wooden counter with twin sinks. Stone walls provide a natural texture, while wooden cabinets above hold various bottles. Sunlight filters through a nearby window, illuminating the earthy tones of the cabinetry and decor.

4.81 out of 5 average rating, 196 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.

4.97 out of 5 average rating, 108 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.

4.89 out of 5 average rating, 343 reviews

Loft in Midland

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. 2 nights min. preferred, 1 night by request. Listing not suitable for ages under 6.

Guesthouse in Victoria Harbour

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.

4.97 out of 5 average rating, 259 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

4.95 out of 5 average rating, 123 reviews

A modern electric fireplace is mounted on the wall, featuring realistic flames that gently flicker over a textured surface. The setting is complemented by a cozy seating area nearby, providing an inviting space for relaxation.

Apartment in Midland

Chez 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.

4.95 out of 5 average rating, 233 reviews

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.

Superhost

A serene lakeside scene is captured at sunrise, with the sun rising over the water behind a cluster of trees. A bench is positioned in the foreground, offering a peaceful view of the tranquil landscape.

Cottage in Midland

4.87 out of 5 average rating, 218 reviews

House on the Hill, HotTub, Relaxation, Bike Trails

Experience the perfect blend of historic charm and modern comfort in this century home. Bask in the refreshing breeze from Georgian Bay and enjoy the tranquility it brings. Explore nearby downtown shops, take advantage of the Trans Canada Trail for walking, running or biking, and discover a variety of local attractions just minutes away.

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Other great vacation rentals in Wyebridge

Superhost

4.9 out of 5 average rating, 52 reviews

A modern retreat on Georgian Bay STRTT-2025-062

KaterynaRating, 5 stars5 months ago

Beautiful home! We absolutely loved the living area. It felt cozy with all the natural light coming in through the ceiling windows. The dining area was great on a snowy day. We played the games and enjoyed the views of the snow-covered pine trees! Loved the location and the house. Would recommend!

4.82 out of 5 average rating, 45 reviews

The image captures a staircase leading to an upper level, with a light blue wall enhancing the entrance area. A white door sits at the bottom, featuring a mail slot. Simple decor includes a sign and a pair of shoes placed near the door.

Guest suite in Midland

Private basement: bedroom, living room, bath, ktch

RobertRating, 5 stars3 weeks ago

the basement apartment was quiet and convenient for me considering I was spending all day outside. it is close to Midland Cultural Center, the YMCA and a nice park by the little.

4.86 out of 5 average rating, 22 reviews

A tranquil beach scene is depicted with soft golden sand leading to calm water. A picnic table is positioned on the sand, surrounded by sparse greenery and framed by a clear blue sky, creating a peaceful atmosphere for relaxation.

Home in Port McNicoll

Cozy Cottage with Private Beach Access

AlexandraRating, 5 stars1 week ago

My family and I recently stayed at Magdalena‘s. The cottage was clean and Magdalena was very friendly and accommodating. There’s beach access and a little playground for children. We enjoyed our stay.

4.89 out of 5 average rating, 19 reviews

A shaded outdoor seating area features a large red umbrella overlooking a serene lakeside view. Comfortable chairs and a table are positioned on the wooden deck, with vibrant flowers surrounding the space. The calm water reflects a clear sky, creating a tranquil atmosphere.

Home in Elmvale

Cozy Lakefront Cottage with Hot tub and Pool.

KreenaRating, 5 stars9 months ago

We went to this cottage for a beautiful romantic weekend getaway and we were happy we got that. The owner of the cottage Necker was very kind and helpful, absolutely loved the place and there was plenty of water activities to do. It was easy to check in, communicate and plenty of peaceful vibes. Recommended 100%, please go visit this cottage it is very well worth it. P.S: we loved the character of the cottage with little artpieces and wall art from all over the globe 🌎.

4.95 out of 5 average rating, 39 reviews

Bungalow in Midland

Boho Hideaway w/ Hot Tub, Sauna & Games

TianaRating, 5 stars1 week ago

I had a fantastic experience staying here! The place was exactly as described—clean, cozy, and well-decorated. The host was friendly and responsive, and check-in was a breeze. The location is super convenient and close to everything, although it is right near a busy road, so it can get a bit noisy at times. That said, everything else more than made up for it. I’d absolutely stay here again and highly recommend it. Thank you for the lovely stay!

5 out of 5 average rating, 28 reviews

A coffee machine is positioned above a wooden slab, with a white mug resting beneath it. The mug contains a freshly brewed coffee, featuring a frothy crema on top. A jar filled with coffee grounds is visible in the background.

Apartment in Midland

Hidden Gem

JoanneRating, 5 stars3 days ago

Truly a hidden gem! The apartment was as described and more - we immediately felt at home. Excellent bed, comfy couch, fully equipped kitchen even nice towels! Loved the outdoor space complete with BBQ. We have marked this as our landing spot when putting our boat on and out of the water in Midland - will be back for sure! Michelle was a very responsive and kind host.

Superhost

Cottage in Port McNicoll

4.93 out of 5 average rating, 43 reviews

Steps to Beach / 1.5h from Toronto

MilaRating, 5 stars3 months ago

We had an amazing a couple of days stay at Dzenana's cozy and well maintained home. I would, for sure, recommend it for any season.

A workspace is presented with two light wooden desks, each paired with a stylish white chair. Above, open shelves display a selection of books, decorative items, and a small plant. Soft natural light filters through a nearby window, enhancing the serene environment.