Cottage vacation rentals in Windsor

A welcome mat rests at the entrance, displaying the phrase 'WELCOME TO THE LAKE' in bold, black lettering. The mat is set against a backdrop of light-colored decking, inviting guests into the home.

4.93 out of 5 average rating, 113 reviews

Lakeside Hydeaway Cottage on Lake Erie w/ Hot Tub

Welcome to Lakeside Hydeaway...truly your home away from home. We are located along Erie Shoreline and tucked away on a quiet street within Essex County Wine Country. Our unique and cozy home is the perfect place to venture out and make memories. Enjoy afternoons playing games on the lawn, soaking your feet in the sand and watching the sunset from your balcony or waterside deck, our home is sure to leave you feeling relaxed. Enjoy late night bonfires or soaks in the hot tub amidst the stars.

A spacious wooden deck extends towards Lake Erie, featuring a grill and two outdoor chairs. The gentle waves can be seen lapping against the rocky shoreline. Lush greenery frames the scene, adding a natural touch to the outdoor space.

4.91 out of 5 average rating, 274 reviews

Lakeview Inn

The Lakeview Inn sits on the North Shore of beautiful Lake Erie. This modern lakehouse is an 8 minute drive to the centre of kingsville where there is multiple breweries and restaurants, a public beach is a 1 minute drive down the road and is right in the centre of Southern Ontario's Wine Country. If you're coming down for a weekend to relax, taste wine or to enjoy the exceptional birding the area has to offer. At the end of your day relax to the sound of the waves brushing up against the shore.

A spacious deck is featured in front of the cottage, equipped with a seating area and umbrellas for shade. The sandy beach leads to the lakefront, while the cottage's large windows provide views of the outdoors and the surrounding trees contribute to a serene setting.

4.99 out of 5 average rating, 119 reviews

"Willow Soul" newly renovated beach front cottage

Willow Soul sits on a beautiful sandy beach, facing breathtaking views of Lake Erie. This quaint little Island is located with just a 5-minute drive to uptown Kingsville. Bustling with amazing restaurants, specialty shops, salons, winery, marina, golfing, and charter fishing services. The cottage has high-speed fibre optics, cable, air conditioning, antenna and open4 seasons Free 2 car parking diagonally on 5th boulevard. At the end of your day relax in this newly renovated beachfront cottage.

A shaded outdoor area features a hot tub under a canopy, surrounded by wooden bar stools. Light beige curtains frame the space, creating a comfortable atmosphere. A wooden table and steps lead to the hot tub, with ample room for relaxation.

4.95 out of 5 average rating, 127 reviews

Chardonnay Bay- Pet Friendly, beach, hot tub!

Beautiful rustic cottage located in Colchester, Ontario! Chardonnay Bay offers 2 bedrooms and a loft, the master bed includes one queen bed, the 2nd bedroom has single bunk beds and the loft has a queen. We offer a full kitchen as well as laundry facilities. Outdoor patio area with hot tub, picnic table and bbq. We are located within a one minute walk to the beautiful Colchester beach, splashpad, park and marina, located on Essex County’s EPIC wine route consisting of over eighteen wineries.

A bright living space is presented with large windows offering stunning lake views. Comfortable seating is arranged around a central coffee table. A dining table for four is positioned nearby, with decorative accents complementing the airy atmosphere. Light floods the room, enhancing its open feel.

5 out of 5 average rating, 239 reviews

The Kiss nTell - Year round - Hot tub - Lake Views

If you “glamp” when you camp, then you’ll appreciate the finer amenities of this boutique style cottage on Lake Erie. Arguably the best views in this tiny cottage community, The Kiss n Tell graces a bluff overlooking the lake - stunning views from every room. Wake to the sound of waves crashing the shore, sunbathe in loungers, dine while the sun glistens on the water, star gaze from the hot tub or sit by a lakeside fire (firewood provided). Endless options w/out leaving this beautiful space.

4.91 out of 5 average rating, 161 reviews

A serene backyard features a circular arrangement of four light-colored Adirondack chairs surrounding a fire pit. Lush green grass extends toward a calm river, with kayaks and paddle boards visible in the distance, framed by trees and bushes, creating a tranquil outdoor space.

Cottage in Belle River

2 bedroom Getaway/lake St.Clair/boatslip

Escape to tranquility at our fully-equipped and cozy home, nestled in a scenic location. Dive into adventure with complimentary kayaks and paddle boards, allowing you to explore the breathtaking natural landscape and even reach Lake St. Claire by kayak. Our kitchen is stocked with all the essentials for culinary delights. The marina and beach are just a 5-minute drive away, while the hockey arena is only 6 minutes away. Perfect for fishing enthusiasts, we even offer daily boat slip rentals.

4.94 out of 5 average rating, 155 reviews

A spacious living area features a light-colored sectional sofa adorned with dark blue and white blankets. A rustic barn door, made of wood, adds character and leads to the bedroom. Two round mirrors are mounted on the wall, reflecting natural light.

Cottage in Lakeshore

Waterfront Luxurious Cottage in Lakeshore, Ontario

Waterfront Modern Executive Cottage with lots of natural light and stunning views. This cottage is a breath of fresh air and provides all of the comforts and conveniences that you need in a luxurious relaxing getaway . The cottage boasts a unique layout that sleeps 4 with a bright fully stocked kitchen and dinette, master bedroom, an eclectic second bedroom, barn doors, Smart TV and plenty of closet space, gas fireplace, swimming pool and giant waterfront backyard with lake access to swim.

A cozy outdoor space is presented, featuring a large deck with seating and an umbrella for shade. Two lounge chairs in white are positioned in the sandy area, next to two kayaks resting on the beach. The blue cottage is visible in the background.

4.89 out of 5 average rating, 193 reviews

3 Bdr Toes In The Sand Beach Cottage on Lake Erie

Located in the heart of wine country, on a Lake Erie sandy beach with great views, family-friendly activities, restaurants and dining. You will love the high ceilings, panoramic views, comfy beds, hearing the waves on the beach, the feeling of your toes in the sand with a cool drink in your hand. This retreat is great for couples, solo adventurers, business travellers, and families (with kids). There is a cozy gas fireplace with 4K TV, Netflix, wifi, & full kitchen. Your Haven awaits you!

Two vibrant yellow Adirondack chairs are positioned on lush green grass, overlooking Lake Erie. The chairs are placed in a serene outdoor setting, accented by a large tree and distant views of the water, creating a tranquil space for relaxation.

4.95 out of 5 average rating, 139 reviews

The Hideaway

This cosy lakeside cabin is nestled in the heart of wine country, along the Shores of beautiful Lake Erie in a very friendly cottage community. The cottage is tastefully decorated with all the amenities of home, perfect for 1 or 2 people, and an amazing view of the lake no matter where you choose to sit. Just minutes away from local wineries. Walk, bike, explore all the region has to offer. Centrally located between Leamington home of Point Pelee national park and Historical Amherstburg.

The house is situated on a spacious lawn, featuring a wooden deck that extends across the back. Large glass doors provide a view into the living area, framed by an array of colorful chairs. Mature trees surround the property, offering privacy.

4.93 out of 5 average rating, 145 reviews

North Shore Retreat

Welcome to North Shore Retreat! Our house sits atop an elevated bluff overlooking Lake Erie and is adjacent to a beautiful ravine surrounded by mature trees. It is a warm, modern, rustic home with a view you will never forget. Our home is walking distance to three of the most established wineries along Lake Erie (Viewpoint Estate Winery, North 42 Degrees and CREW). This space has everything you need to unwind, cook, disconnect, relax, enjoy wildlife and take care of yourself.

Adirondack chairs are arranged on a spacious deck overlooking Lake Erie, with a fire pit nearby. Lush greenery frames the scene, enhancing the connection to nature, while the calm water reflects the sky, creating a serene view.

5 out of 5 average rating, 122 reviews

Waterside Lakehouse - Lake Erie & EPIC Wineries

Welcome to Waterside Lakehouse on the shores of Lake Erie and nestled among the EPIC Wineries of Essex County. Take in the magnificent views of Lake Erie from the 'infinity deck' or take a short walk (5 min.) to the public beach, harbour and marina in the Village of Colchester. The harbour features a park with a splash pad for the kids, pirate ship climbers and a pier that can be the perfect spot for fishing. You are minutes away from a number of the best Ontario wineries. Enjoy!

A charming cottage is presented with a welcoming front porch and a neatly paved pathway leading to the entrance. Lush greenery and carefully arranged landscaping surround the home, while a tall chimney adds character. Bright blue skies peek through the trees, creating a serene setting.

4.79 out of 5 average rating, 174 reviews

Lakeside getaway

Welcome to Lake Erie and the village of Colchester. Enjoy this premier location with views of the lake and easy access to many local amenities. Families will enjoy the splash pad, play center, public beach, harbour and public changerooms/toilets so close you can see from the window. Friends and couples are well situated to explore local wineries and breweries, 3 of which are less than 10 minutes away by bicycle, and many more accessible via bike lanes along the HWY 50 wine route

Popular amenities for Windsor cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

A hot tub is positioned on a deck overlooking Lake Erie, with a person’s foot visible in the bubbling water. The horizon reveals a vibrant sunset, blending golden and orange hues. The silhouette of a railing and tree branches frames the relaxing scene.

4.85 out of 5 average rating, 105 reviews

The Julia Kennedy Beach House with Hot tub

A charming cottage exterior is seen, featuring a well-maintained front yard with a mixture of grass and decorative stones. A concrete driveway leads up to the entrance, where red seating is positioned on a covered porch, providing a welcoming sight for visitors.

4.96 out of 5 average rating, 72 reviews

2-bedroom with hot tub,200 steps from the beach

Cottage in Brownstown Charter Township

A tranquil sunset over the water is captured, where warm orange and yellow hues blend into the soft blue of the evening sky. A wooden dock is visible in the foreground, with trees silhouetted along the shoreline, providing a serene backdrop.

4.92 out of 5 average rating, 140 reviews

Waterfront home with amazing views & great fishing

A serene outdoor space features several Adirondack chairs arranged in a circle, facing a calm lake. A fire pit is centered among the seating, with a hot tub visible in the background. Sunlight reflects on the water, creating a peaceful ambiance.

4.87 out of 5 average rating, 340 reviews

Year Round Hot Tub & Beautiful Views Cottage

4.95 out of 5 average rating, 38 reviews

A serene lakeside view captures the calm waters of Lake St. Clair, reflecting soft, muted clouds and a setting sun. Sandy beach stretches along the shore, complemented by scattered branches. Lush trees line the background, providing a natural border to the tranquil scene.

Cottage in Saint Joachim

Moe’s on the Lake: 2 bedroom waterfront cottage

An outdoor patio area overlooks Lake Erie, featuring several Adirondack chairs positioned for sunset views. The sky is painted in shades of pink and orange, with the calming water in the distance. Steps lead down from the patio to the shoreline, framed by lush greenery.

4.89 out of 5 average rating, 110 reviews

Erie Shores Lakehouse! · Sunsets & Hot Tub

A charming cottage is situated on a landscaped lawn, flanked by well-maintained shrubbery. Two Adirondack chairs are placed in front of the home, inviting relaxation. A gravel driveway leads alongside the cottage, while trees and greenery create a serene atmosphere.

4.81 out of 5 average rating, 86 reviews

Yellow Cardinal Lake Cottage

A waterfront view showcases the Casa del Lago, highlighting its spacious deck and outdoor sitting area. Two kayaks are securely mounted on the wall, while the sandy beach leads to the tranquil waters of Lake Erie, offering a scenic backdrop of nearby homes and greenery.

4.88 out of 5 average rating, 121 reviews

Hot Tub, Sunsets and Moon lit Lakehouse!

Pet-friendly cottage rentals

A serene outdoor deck with comfortable seating is shown, framed by a large tree. The sun rises over the calm waters of Lake Erie, casting a warm glow. Lush greenery and flowers enhance the tranquil atmosphere, inviting moments of relaxation.

5 out of 5 average rating, 87 reviews

Reveries on the Lake- Kingsville cottage

A cozy stone cabin is set amid lush greenery, showcasing a blend of natural stone and wood siding. The structure features a gently sloping roof and multiple windows, providing a warm and welcoming appearance against the blue sky.

4.93 out of 5 average rating, 136 reviews

The Coziest Cottage in Essex County's Wine Country

4.98 out of 5 average rating, 53 reviews

A view of Lake Erie is framed by a lush tree, with a wooden deck visible in the foreground. A table with black chairs is positioned by the water, inviting relaxation with a serene backdrop of the lake's calm surface.

Cottage in Amherstburg

A Lakeside View

4.98 out of 5 average rating, 44 reviews

Cozy Cottage on Cedar Creek with Game Room

An outdoor fire pit area is surrounded by five red Adirondack chairs, arranged around a circular stone base. Two wooden benches provide additional seating. In the background, the cottage’s exterior is visible with warm lighting, and a cedar sauna can be seen to the left.

4.9 out of 5 average rating, 90 reviews

Sauna, stunning Lake Erie view, lakefront retreat

The exterior of the cottage features a welcoming entrance with a subtle decorative wheel design beside the door. Soft lighting illuminates the walkways and surrounding garden areas, highlighted by plants in decorative pots. Windows frame the entrance, offering glimpses of the interior.

4.94 out of 5 average rating, 98 reviews

Lake Erie Escape Cottage - escape and explore

5 out of 5 average rating, 54 reviews

The outdoor area features a smooth stone patio surrounded by trees and grass. A brick wall provides privacy, while a wooden bench and two chairs offer seating options. A sliding glass door leads to the interior, enhancing the connection between indoor and outdoor spaces.

Cottage in Belle River

Urban Cottage Adorable Shabby Chic Getaway for 2

The exterior of the cottage is softly illuminated in the evening light, highlighting a welcoming front porch with multiple seating areas. A pathway is lined with solar lights, leading up to the entrance. Surrounding greenery adds to the tranquil outdoor setting.

4.92 out of 5 average rating, 38 reviews

Crabapple Cottage

Private cottage rentals

An outdoor view features two cottages set against a backdrop of trees and green grass. A stone pathway leads to red chairs arranged on a patio area, inviting relaxation. The cottages display a contemporary design, and Lake Erie's shoreline is indicated in the distance.

5 out of 5 average rating, 15 reviews

Hideaway on the Lake, 2nd Cottage Available!

An expansive wooden deck overlooks the lake, with multiple adirondack chairs arranged for relaxation. A grill is positioned nearby, and an umbrella offers shade. The scene is illuminated by a warm sunset, casting soft light across the surface of the water.

4.96 out of 5 average rating, 91 reviews

Southern Exposure on Lake Erie

Superhost

4.67 out of 5 average rating, 12 reviews

Serene Cottage, 1km from Point Pelee National Park

A charming exterior of a cottage is displayed, showcasing a large wrap-around deck with comfortable seating. Two front-facing windows allow natural light to enter, while a decorative stone accent wall adds texture. Lush green landscaping is present in the foreground, enhancing the inviting atmosphere.

5 out of 5 average rating, 82 reviews

Unique A-Frame Cottage Steps away from the Beach!

A charming lake house is positioned along the shore, framed by lush trees and bordered by large rocks. A spacious outdoor patio is furnished with seating and a red umbrella, complemented by a vibrant sunset sky casting warm tones over the scene.

4.87 out of 5 average rating, 53 reviews

On The Rocks

5 out of 5 average rating, 15 reviews

A wooden dock extends towards Lake Erie, flanked by two black Adirondack chairs. The dock is surrounded by green grass and plants, with a large tree providing shade. The serene lake view is visible in the background under a clear sky.

Cottage in Amherstburg

Blue Break Cottage

A serene sunset casts vibrant hues across the sky, reflecting on the calm waters of Lake Erie. The shoreline is bordered by sandy beach, with gentle waves lapping at the shore. A silhouetted tree stands to the right, enhancing the tranquil atmosphere.

4.85 out of 5 average rating, 84 reviews

Sunset View Bunky Retreat -Beach/Explore/Relax :)

Two red Adirondack chairs are positioned on a wooden deck, facing the calm waters of Lake Erie. A small round table stands between the chairs, complementing the tranquil lakeside setting against a clear blue sky.