Cottage holiday rentals in Windsor

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Top-rated cottage rentals in Windsor

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Guest favourite
An aerial view captures the charming cottage situated along a rocky shore, surrounded by vibrant autumn foliage. The cottage features a red roof and a spacious outdoor area, with the serene water of Lake Erie creating a picturesque backdrop.
Cottage in Leamington
4.9 out of 5 average rating, 128 reviews

Waterfront - Hot Tub - 3Bed Cottage - Pet Friendly

Welcome to your private 3-bedroom waterfront retreat in Leamington. Enjoy stunning sunrises and sunsets with breathtaking water views from both the front and back of the cottage, visible from every room. Relax with your morning coffee or evening beverage, or unwind in the indoor hot tub with lake view. Nearby attractions include Point Pelee National Park, wineries, golf courses, and many more. Leamington’s vibrant food scene - its authentic Mexican cuisine adds a flavorful touch to your stay.

Top guest favourite
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
4.95 out of 5 average rating, 38 reviews

Moe’s on the Lake: 2 bedroom waterfront cottage

Moe’s place on the lake is the perfect sized space just far enough to feel the peace of nature’s escape, yet close enough to all of life’s conveniences. All seasons highlight a different slice of nature’s beauty. Summer brings picturesque sunsets, swimming, and listening to the glistening waves of Lake St.Clair. “Fall” in love with a crackling fire on the deck, sip some wine and let go. Explore a winter wonderland and warm up with a soak in the hot tub feeling the drops of sparkling snowfall.

Top guest favourite
Cottage in Leamington
5 out of 5 average rating, 35 reviews

Parkview Boho Cottage 4 - Birch Burrow

With a beautiful park sprawled outside your front door and a short walk to the beach, this elegant boho space is newly renovated, designed for comfort and relaxation. It is perfect for couples, solo travelers, or anyone seeking a quiet escape from the everyday hustle. Whether you're looking to unwind, explore Point Pelee National Park (FREE parkpass provided), catch the Ferry to Pelee Island, or visit the local wineries, this little cottage offers everything you need for a memorable escape.

Guest favourite
A view of Lake Erie is captured from the cottage's porch, showcasing vibrant greenery and a serene shoreline. Comfortable outdoor seating faces the water, while the sunset casts warm hues across the sky. A wooden dock extends into the lake, enhancing the tranquil setting.
Cottage in Amherstburg
4.87 out of 5 average rating, 45 reviews

Lakeside Living

Enjoy a relaxing getaway on Lake Erie, minutes away from downtown, Historic Amherstburg. Surrounded by beach and wildlife, our cozy cottage is equipped for all renters. In the heart of #Epicwinecountry, this spot is perfect for wine tours, breweries, bird watching, fishing, kayaking, boating etc. This cottage is located in a country club with access to baseball diamonds, beach volleyball, tennis, basketball a boat launch and more. Only a few minutes down from Holiday Beach and hiking trails.

Guest favourite
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 favourite
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, 155 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.

Guest favourite
A cozy bedroom features a spacious bed adorned with decorative pillows and a textured blanket. Natural light enters through the window, illuminating the soft grey walls. A bedside table holds a lamp, and a framed landscape image of water and clouds hangs above the bed.
Cottage in Leamington
4.94 out of 5 average rating, 108 reviews

Bird's Nest at Hillman Marsh - One Bedroom Cottage

Welcome to the Bird's Nest at Hillman Marsh in Leamington, Ontario! Available all year round you can enjoy this one bedroom cottage . Whether you are here to bird watch, enjoy the beach or just to relax, this cottage has it all. Located just 5 mins from Hillman Marsh, 10 mins from Wheatley Provincial Park, 15 mins from Point Pelee and downtown Leamington. Public boat launch and beach nearby. Large back deck has a covered gazebo and includes a BBQ and fire pit. Wifi is now available!

Guest favourite
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.
Cottage in Brownstown Charter Township
4.92 out of 5 average rating, 140 reviews

Waterfront home with amazing views & great fishing

Beautiful and private backyard looking out at picturesque water views. Has a private dock to pull your boat up to. There is a marina, as well as a public boat launch less than 5 minutes away and Lake Erie is only a 10-minute boat ride from the house. You can also access the Huron River using kayaks within 5 minutes from our dock. The backyard has a patio and a built-in fire pit with a hot tub to enjoy both summer and winter nights with gorgeous sunsets over the water as your backdrop.

Guest favourite
The modern kitchen features white cabinetry, stainless steel appliances, and a large island with seating for four. A unique light fixture hangs above the island, while natural light fills the space through the nearby window, enhancing the clean design.
Cottage in Spring Garden
4.95 out of 5 average rating, 22 reviews

Spring Garden Suite | Nature | Family | Comfort

★ “Life is better in the garden! “ Welcome to the Spring Garden Suite. This meticulously restored cozy home is nestled in the serenity woods of Spring Garden Natural Area. Has all the comforts of home ,full size kitchen and living area with unlimited fiber internet, spacious 3 bedrooms and a modern chic bathroom. In addition, enjoy your evening sitting on our backyard patio enjoying the tranquil views of the prairie and catching a glimpse of the many deers running through the woods.

Top guest favourite
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, 249 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 favourite
A lakeside deck features two black Adirondack chairs, positioned for unobstructed views of the tranquil water. The blue horizon meets a clear sky, while surrounding greenery and rocks enhance the natural setting.
Cottage in Amherstburg
4.99 out of 5 average rating, 72 reviews

The Stranded Paddle Getaway

Enjoy the winding drive through Big Creek Marsh and admire all the local wildlife leading to our lakefront cottage. Our cottage is a charming 2 bedroom 1 bath property with hot tub (new) available year-round. Sleeps five guests comfortably. Fully equipped kitchen and BBQ to prepare all your favourite recipes. Lakeside deck, hot tub and fire table to enjoy evening sunsets. A steel ladder on the break wall provides easy access into and out of the lake.

Top guest favourite
A private outdoor space is highlighted by a hot tub and seating areas, featuring contemporary furniture in neutral tones. Red lounge chairs are positioned on a sandy beach area, with a waterfront view stretching to the horizon, bordered by trees and a pier in the distance.
Cottage in Amherstburg
4.96 out of 5 average rating, 283 reviews

Year Round Hot Tub, The Beach House

Welcome to The Beach House! This home features a private hot tub plus your very own private beach. The house will accommodate 8 people. Mins from Windsor, Lasalle and downtown Amherstburg. Close to dining, shopping and Essex's beautiful wineries. Enjoy gorgeous sunsets, sipping your coffee on the back deck in the mornings, relaxing in the lounge chairs catching some rays, splashing your toes in the water! Come with your family and friends.

Popular amenities for cottage rentals in Windsor

Quick stats about cottage rentals in Windsor

  • Nightly prices starting at

    Windsor holiday rentals start at € 121 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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