Cottage holiday rentals in Windsor

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Top-rated cottage rentals in Windsor

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Cottage in Essex
4.93 out of 5 average rating, 110 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.

Guest favourite
Cottage in Kingsville
4.9 out of 5 average rating, 268 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 favourite
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 favourite
Cottage in Essex
4.93 out of 5 average rating, 409 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! ♥️

Guest favourite
Cottage in Essex
4.95 out of 5 average rating, 125 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.

Top Guest favourite
Cottage in Essex
5 out of 5 average rating, 234 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 favourite
Cottage in Essex
4.89 out of 5 average rating, 190 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!

Top Guest favourite
Cottage in Essex
4.93 out of 5 average rating, 143 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 favourite
Cottage in Essex
5 out of 5 average rating, 121 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 favourite
Cottage in Essex
4.79 out of 5 average rating, 170 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

Guest favourite
Cottage in Amherstburg
4.96 out of 5 average rating, 276 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.

Guest favourite
Cottage in Kingsville
4.86 out of 5 average rating, 115 reviews

Erie Haven Cottage

Our cozy Erie Haven Cottage in Kingsville Ontario, right on the beautiful shores of Lake Erie is a charming retreat that offers the perfect getaway for those seeking tranquility and relaxation. Our cottage features a warm, inviting atmosphere, providing a comfortable space to unwind and enjoy the stunning lake views. With its prime location, you'll have direct access to a sandy beach just steps away from your doorstep.

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