Vacation rentals in Windsor

4.9 out of 5 average rating, 287 reviews

Cottage in Essex

Year Round Hot Tub & Beautiful Views Cottage

Welcome to the Cozy Lakeside Cottage! Located within the village of Colchester, right on Lake Erie, nestled in the middle of Essex Wine Country. This cottage features 4 beds (A queen bed in the primary bedroom, one bunk bed with a queen base and a full upper bunk in the 2nd bedroom, plus an additional murphy bed on the main floor) Full kitchen, indoor dining, outdoor dining, 4 person hot tub & stunning views! Colchester Beach, Restaurants, Park & Marina just steps away! A truly relaxing escape.

4.99 out of 5 average rating, 105 reviews

An outdoor seating area features gray Adirondack chairs arranged around a fire pit on the sandy beach. In the background, the cottage is visible with large windows and a spacious deck, equipped with lounge chairs and a dining area shaded by an umbrella.

Cottage in Kingsville

"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.

4.93 out of 5 average rating, 103 reviews

Home in Essex

Wine Down by the Lake

Hot tub, Lake views, wineries and golf? Sound perfect? It is and you have picked the perfect spot! A beautiful piece of heaven steps from Lake Erie. Whether you choose to relax in this amazing home, or enjoy the many wineries in walking distance, you have picked a real gem!! You can enjoy lake views from the rear deck or hot tub while sipping your wine. This home is perfect for a small bridal party, girls weekend or for couples looking to get away and explore what the area has to offer!

4.89 out of 5 average rating, 186 reviews

A serene view of Lake Erie is captured from a wooden deck, showing soft sandy beach and gentle waves lapping at the shore. Sunlight reflects on the water's surface, creating a shimmering effect. A boat dock is visible nearby, enhancing the tranquil atmosphere.

Cottage in Essex

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!

4.89 out of 5 average rating, 211 reviews

Apartment in Leamington

Park Bungalow #4 - Seacliff Beach Suites

Welcome to the Park Bungalow in Leamington, Ontario. Beautifully renovated flat in Leamington's best location! Welcoming pets and nestled beside Seacliff Park and Beach, and abundant restaurants, this listing has everything you need. A fully equipped kitchen and large living area make this an ideal place for your visit. Front and back yard for your use with large private paved area (fires and loud noises not allowed - please respect our neighbors). Two cars maximum. Tv's in all rooms.

4.93 out of 5 average rating, 155 reviews

A spacious patio area is visible, featuring a comfortable lounge set with gray cushions. Large glass doors provide access to the interior, while a neatly landscaped lawn surrounds the wooden deck. Potted plants are placed strategically for added greenery.

Cottage in Essex

Bright, Peaceful Lakefront ~Sunporch, BBQ, firepit

Welcome to A Day at the Lake! Relaxation, a cozy space and comfortable beds located here. Enjoy the light and airy feel of this lakefront cottage with plenty of natural light and cool breezes off Lake Erie. Located on Clark Beach in Harrow; near wineries, beaches, conservation areas, cycling and paddling routes. Welcome birders, beach goers, winery/brewing enthusiasts, cyclists and runners. Spring and summer dates book fast so be sure to reserve early to avoid disappointment.

4.95 out of 5 average rating, 147 reviews

A spacious wooden deck features a dining table with six chairs, a lounge area with sectional seating, and an outdoor grill. A large umbrella offers shade, while surrounding trees provide a natural backdrop, creating an inviting space for relaxation and family gatherings.

Home in Essex

*KID & FAMILY FRIENDLY* Shores of Erie Guest House

Welcome to our family-friendly vacation home in the charming village of Colchester, Ontario! Nestled in the heart of wine country, our spacious two-story house is perfect for families. Our property is renowned for its welcoming atmosphere, complete with a sandbox, an extensive collection of board games, books, BBQ, firepit, ping pong, fooseball, and even a crib for your littlest ones. We're excited to provide a memorable stay for your family, where adventure and relaxation await!

4.99 out of 5 average rating, 239 reviews

Home in Kingsville

La Perla - Lakefront Retreat in Wine Country!

Indulge in the stunning views of Lake Erie while relaxing at a one-of-a-kind vacation property. Experience the perfect harmony of contemporary comfort and vintage allure in every corner of our space. Nestled in Canada's most southern wine region, we're minutes from craft breweries, golf, dining, and Point Pelee National Park. Enjoy zero-contact check-in, pristine cleaning, luxurious linens and a chefs kitchen! Contact us today to begin planning your unforgettable getaway!

4.96 out of 5 average rating, 111 reviews

Home in Amherstburg

The Lake House Ontario

Located at the start of the award winning EPIC Wine Trail, modern home 2 sides open to beautiful Lake Erie. Amazing sunset views from the hot tub. Sleeps 6 w 2 bdrms both w super comfy beds & 1 dbl pull out sofa bed, 1.5 baths, hardwood, gourmet kitchen, cozy gas fireplace, jacuzzi tub, gas BBQ, gas fire table - perfect for fun, romance or celebrating friendships. Beach just steps away. Canada's southernmost tip Point Pelee National Park, golf, museums, all just minutes away!

4.84 out of 5 average rating, 124 reviews

A spacious living area is highlighted by an arched entryway and hardwood flooring. Two comfortable recliners are arranged towards the window, allowing for natural light to enter. A dining area with modern bar stools can be seen in the background, complementing the overall inviting space.

Home in The Core

Couple's Romantic Retreat with hot tub, fire pit.

Romantic and soothing discreet hideaway. Come to relax, reunite and enjoy the night. This beautiful unit features: -private backyard Oasis with Hot tub, cedar Gazebo, outdoor Tv and sound bar, accent lighting, bbq and fire pit. -king size bed; -couple's spa shower; -massage table -fully stocked chef's kitchen; -private garage parking; -nearby parks and trails; -plus all of the comforts of being in the city. Everything you need to enjoy a restful and relaxing weekend away.

4.89 out of 5 average rating, 146 reviews

A waterfront deck features a shaded table and chairs under an umbrella, overlooking Lake Erie. Wooden benches, a fire pit, and a pebble-covered area are visible, complemented by lush green grass and surrounding trees.

Cottage in Leamington

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.

4.94 out of 5 average rating, 151 reviews

Cottage in Leamington

Beachfront, Hot tub, Sunsets, Moonlight, Romance,

Check out this magnificent cottage on the Shores of Lake Erie. This cozy, 2 bedroom waterfront property is sparkling clean and extremely comfortable. It's the perfect getaway for any nature lover! It's nestled in a quiet lakefront area with a beach when water levels are not high, and a relaxing hot tub with a view of the stunning sunsets over Lake Erie. A stones throw from Point Pelee National Park & Hillman Marsh

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What guests are saying

Lakefront cottage in heart of wine country

5 out of 5 average rating, 27 reviews7 months ago

Love this little gem! Great location to bike ride to wineries. View is priceless! Lakehouse is beautiful! Elie (owner) is so pleasant, quick to respond and very accommodating. Such a quick drive from Detroit. This is my 3rd time renting and planning to be back soon!

Cottage in Essex

What guests are saying

Lakeside Beach Loft

5 out of 5 average rating, 9 reviews6 months ago

Clean, lovely, comfort cozy loft. Laurie was responsive, answering questions and checking in on us, if there was anything we needed. We booked this loft to do some biking riding around the area, including Pelee Island. The loft is close to Kingsville terminal, departure to Pelee Island (certain times of the year), but due to weather conditions, the boats departure and return was changed to Leamington. Ontario Ferries did notify us in advance of the change the night before departure. I would book Laurie’s loft again. Thanks Laurie

Loft in Kingsville

What guests are saying

Southpoint Retreat - King Size Bed

4.92 out of 5 average rating, 26 reviews3 days ago

We had an amazing four night stay celebrating my mother-in-laws 86th birthday! She loved the peacefulness of the place and the kitchen impressed her with how well it was stocked. The outdoor chiminea and wood that was provided was also fantastic for my husband and his father!

Home in Leamington

What guests are saying

Shore To Please-Tranquil Getaway

4.83 out of 5 average rating, 36 reviews1 week ago

We stayed here for our wedding and it was a great find! Lots of rentals on the street for family but we had the best setup for the grooms getting ready photos. A huge yard on the water and lots of natural light. Place also has A newer hot tub that was easy to use and could hold up to 6 easily. Everything was clean and exactly as pictured. Beds were comfy and the bathroom was gorgeously renovated. The kitchen had everything we needed. Would definitely stay here again!

Home in Amherstburg

What guests are saying

Luxurious Lakeside Oasis NEW

5 out of 5 average rating, 7 reviews5 months ago

An absolute beautiful place for your getaway. Clean and spacious with every item you can ask for without having to pack it all and bring it with you. The view is absolutely beautiful with amazing sunsets. There is lots to do without ever leaving the house; however, it is in the middle of wine country and a few little towns that are lovely to see and visit. The host was easy to reach, kind and accommodating. We will definitely be back!!

Home in Essex

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Popular amenities for Windsor vacation rentals

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Stay near Windsor's top sights

Little Caesars Arena159 locals recommend

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Eastern Market294 locals recommend

House rentals in Windsor

4.85 out of 5 average rating, 133 reviews

Home in The Core

3 Bed Bright Modern Home in Heart of Walkerville

4.97 out of 5 average rating, 189 reviews

A spacious living area features a sectional sofa and a coffee table, with soft lighting provided by a pendant light. A dining table with white chairs sits nearby, and an image of a bridge adorns the wall, contributing to a modern and inviting atmosphere.

Home in Windsor

Shalom - Modern Spacious Home, 4BR + 4Beds + 3BA

4.87 out of 5 average rating, 118 reviews

The open living space features a sectional sofa, a round accent chair, and a coffee table. Natural light fills the room, highlighting the gray walls and decorative circular mirrors. A dining area is visible through an archway, showcasing a table with seating for four.

Home in Detroit

3 Bedroom Private Home Minutes from Downtown

4.86 out of 5 average rating, 153 reviews

The upstairs bedroom features two double beds, each dressed in white linens with soft, fur throws draped on top. Light fills the space through large sliding glass doors leading to a balcony, with nature-themed wall art accentuating the neutral decor.

Home in LaSalle

Quiet LaSalle Newly Renovated Entire Country Home

4.87 out of 5 average rating, 125 reviews

A well-lit entryway is presented, featuring a staircase with a black railing and wooden paneling. A painting is displayed on the wall, complementing the modern design. A laundry area is visible to the right, equipped with stacked washing machine and dryer.

Home in The Core

Beautiful 3Bedroom 2Bath Home free parking&laundry

4.9 out of 5 average rating, 103 reviews

A spacious living area is furnished with a modern gray sofa and a sleek coffee table, situated near large windows that offer views of Lake Erie. A stone fireplace serves as a focal point, while a dining area is visible in the background.

Home in Amherstburg

That place by the Lake

4.89 out of 5 average rating, 76 reviews

A fenced yard surrounds the house, providing privacy and a sense of security. A large tree casts a gentle shadow across the grassy area. The building features a simple design with multiple windows, allowing natural light to fill the interior.

Home in Melvindale

A lovely home with a big yard

4.9 out of 5 average rating, 121 reviews

The exterior of a single-story brick house is presented, featuring a small front porch with steps leading to a black railing. A fenced area is visible, with a grassy yard and a paved driveway extending towards the front. Nearby, trash bins are placed along the curb.

Home in Windsor

Full house - 5 bed, 2 bath

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Other great vacation rentals in Windsor

4.98 out of 5 average rating, 103 reviews

A spacious waterfront patio is shown, featuring comfortable lounge chairs oriented towards serene lake views. Vibrant floral arrangements are visible in planters, complementing the natural scenery. Cloudy skies create a calm atmosphere above the tranquil waters of Lake Erie.

Cottage in Kingsville

Relaxing lakefront cottage near wineries and beach

4.96 out of 5 average rating, 77 reviews

A well-maintained outdoor area features a lush green lawn leading to a wooden dock extending into the tranquil lake. A firepit, surrounded by stone, is situated near the edge of the lawn, with decorative landscaping elements adding charm to the space.

Home in Amherstburg

Erie View Lakehouse - Serene and Spacious

4.98 out of 5 average rating, 40 reviews

A sandy beach area is framed by a large tree, providing shade over deck chairs in bright colors. A wooden picnic table is positioned nearby, with a clear view of the lake and a distant sailboat. Sunlight filters through the leaves, creating a serene atmosphere.

Cottage in Leamington

Sunsets by the Bay - Your Waterfront Oasis

5 out of 5 average rating, 5 reviews

A serene rooftop pool is framed by modern lounge cabanas. The clear blue water reflects sunlight, while city views are visible in the background. Sleek tile flooring surrounds the pool area, providing a spacious environment for relaxation and leisure.

Loft in Wyandotte

Loft, Open Concept, Balcony 2 Bed, Pool Gym, Wifi

5 out of 5 average rating, 8 reviews

A spacious living area features a large gray sectional sofa adorned with patterned pillows. A marble coffee table sits in the center on a light rug, while natural light floods the room through multiple windows. The open layout leads to a dining area in the background.

Home in Kingsville

Large luxury home, beach access, backyard, quiet

Apartment in Grosse Pointe Park

Aerial view showcasing a tranquil neighborhood with a mix of residential homes and tree-lined streets. The expanse of Lake St. Clair is visible in the background, providing a serene backdrop to the well-maintained properties and greenery below.

4.86 out of 5 average rating, 14 reviews

Villa del Lago Grosse Pointe Park King with 2 Queens

5 out of 5 average rating, 4 reviews

An above-ground pool is centered in a private backyard, surrounded by lush greenery and wooden decking. The clear blue water reflects the sky, providing a refreshing space for relaxation. Nearby seating can be seen within the fenced area, enhancing the outdoor atmosphere.

Home in Riverside

Spacious Family Getaway w/ Pool -Sleeps 12 - 2 TVs