
Cottage vacation rentals in Windsor
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Top-rated cottage rentals in Windsor
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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.

"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.

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! ♥️

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.

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.

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.

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.

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.

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!

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

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

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
Cottage rentals with a hot tub

Lakeside Hydeaway Cottage on Lake Erie w/ Hot Tub

Waterfront - Hot Tub - 3Bed Cottage - Pet Friendly

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

Waterfront home with amazing views & great fishing

Moe’s on the Lake: 2 bedroom waterfront cottage

Sunrise Retreat - Lakefront Cottage w/ Hot Tub

Chardonnay Bay- Pet Friendly, beach, hot tub!

Casa Azul : Your Lake Erie Cottage Oasis
Pet-friendly cottage rentals

Reveries on the Lake- Kingsville cottage

A Lakeside View

"That 70's Cottage" (on Lake Erie!) Free Firewood!

Cozy Cottage

Cozy waterfront | kayaks, fishing, fire-pit, games

Sauna, stunning Lake Erie view, lakefront retreat

Pura Vida Beach House-100 ft. of Beachfront

Lake Erie Escape Cottage - escape and explore
Private cottage rentals

Lakefront cottage in heart of wine country

Hideaway on the Lake, 2nd Cottage Available!

Southern Exposure on Lake Erie

On The Rocks Lakehouse - Point Pelee, Leamington

Hickory Lakehouse Retreat

Blue Break Cottage

The Canadian Dream

Biggest Beach on Point Pelee Dr - The Parker House
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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- Ford Field
- Little Caesars Arena
- Point Pelee National Park
- Comerica Park
- Michigan Stadium
- Detroit Zoo
- Detroit Golf Club
- University of Michigan Museum of Art
- Motown Museum
- Indianwood Golf & Country Club
- Warren Community Center
- Seven Lakes State Park
- Rolling Hills Water Park
- Bloomfield Hills Country Club
- Seymour Lake Township Park
- Oakland Hills Country Club
- Maumee Bay State Park
- Wesburn Golf & Country Club
- Seven Lakes Championship Golf & Estates
- Mt. Brighton Ski Resort
- Grosse Ile Golf & Country Club
- Country Club of Detroit
- Ambassador Golf Club
- South Bass Island State Park