Cottage vacation rentals in Windsor

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Top-rated cottage rentals in Windsor

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Guest favorite
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.
Cottage in Kingsville
4.9 out of 5 average rating, 273 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.

Top guest favorite
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.
Cottage in Kingsville
4.99 out of 5 average rating, 118 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.

Guest favorite
A cozy interior space features floor-to-ceiling windows overlooking the lake, offering stunning views at sunset. A soft, inviting mat is placed on the floor, surrounded by various plants and decorative pillows. Warm light emanates from a lamp, creating a serene ambiance.
Cottage in Essex
4.93 out of 5 average rating, 410 reviews

Your Soulstice Studio

Become one with nature in this cozy cottage with an expansive view of the lake. Let yourself be absorbed by the sound of waves, birds and silence in the early morning hours. Sudden urge to do some yoga? No problem you have mats, blocks and bolsters to fulfill you ever stretching need! Your Soulstice is an up and coming yoga and massage studio that has been 2 years in the making. Now that it’s ready to open it’s doors, it needs a wee income to repay the “bank of mom” to show my appreciation! ♥️

Top guest favorite
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.
Cottage in Essex
5 out of 5 average rating, 236 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.

Guest favorite
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
4.91 out of 5 average rating, 161 reviews

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.

Guest favorite
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
4.94 out of 5 average rating, 154 reviews

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.

Top guest favorite
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.
Cottage in Essex
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.

Top guest favorite
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.
Cottage in Essex
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.

Top guest favorite
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.
Cottage in Essex
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!

Guest favorite
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.
Cottage in Essex
4.79 out of 5 average rating, 172 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

Top guest favorite
An inviting interior showcases a cozy sleeping area with a spacious bed, complemented by light-colored wood paneling. The kitchen features vibrant blue cabinets and modern appliances, while a clean bathroom is equipped with essential toiletries and stylish fixtures. Natural light enhances the overall ambiance.
Cottage in Kingsville
5 out of 5 average rating, 244 reviews

PELICAN PLACE Cottage ❤ Kingsville WALK EVERYWHERE

WALK EVERYWHERE! Kingsville's famous eateries, bakeries, coffee houses, trendy shops, breweries, Estate of health spa, Lakeside park, Pelee Ferry(Aug - Dec) accessible from the greenway. GATEWAY to all Wineries, Golf courses, Point Pelee park & surrounding communities. Enjoy our cozy 2 Queen bd cottage inside & out. BBQ, covered patio dining area. Ample parking, quiet street. Special Coupons & discounts incl'd for our guests. We look forward to hosting you STR25-022 STR

Top guest favorite
Two wooden Adirondack chairs are positioned on a wooden deck, facing Lake Erie's calm waters. A simple wooden bench is situated nearby, all set against a clear blue sky, creating a peaceful environment for relaxation.
Cottage in Leamington
4.89 out of 5 average rating, 148 reviews

Erie Shores Cottages

Welcome to the Cottage Located on the waterfront of Lake Erie in beautiful Leamington Ontario and only a few minutes from Point Pelee National Park. Point Pelee National Park is world renowned for it's bird watching and monarch butterfly migration. Also enjoy canoeing, kayaking, hiking, biking, endless beaches, picnic areas/pavillions and boardwalks. Three restaurants within walking distance and wine tours available from local wineries No Smoking.

Popular amenities for Windsor cottage rentals

Quick stats about cottage rentals in Windsor

  • Nightly prices starting at

    Windsor vacation rentals start at G$29,249 GYD per night before taxes and fees

  • Verified guest reviews

    Over 20 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor rentals

  • 4.6 Average rating

    Windsor stays receive an average rating of 4.6 out of 5 from guests

  • Nearby attractions

    Windsor's top spots, include Little Caesars Arena, Comerica Park, and Ford Field

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