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.

4.93 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.

Top guest favorite

A wooden deck features swings overlooking the lake, with colorful chairs positioned nearby. A stone fire pit sits surrounded by outdoor seating, complemented by the serene lake view and grassy area that extends towards the water.

4.99 out of 5 average rating, 305 reviews

It's a 'Shore' thing - Executive Retreat

Year round beautiful upscale 3 bedroom modern, chic cottage. sleeps 6. Outstanding views of lake. Relax in the Hot tub, Gas fireplace for cool nights. Outdoor gas fire table. Fabulous for romantic getaways, GIRLS 'just wanna have fun' weekends, or friends gathering .Beach/boat launch in walking distance. Gas BBQ, central A/C, wifi. Even swings overlooking the lake!! Great area for Wineries, Birding, Fishing, sightseeing, Pelee Island, Conservation areas. EV outlet on property.

Top guest favorite

Home in Kingsville

4.99 out of 5 average rating, 239 reviews

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.

A serene outdoor space overlooking the lake features a concrete patio with a fire pit at the center. Wooden chairs are positioned nearby, complemented by large rocks along the water's edge. A staircase leads to a deck, providing access to the stunning lakeside view.

4.95 out of 5 average rating, 150 reviews

Sunrise Retreat - Lakefront Cottage w/ Hot Tub

This beautiful tranquil cottage is the perfect escape from your everyday frenzied life. Perfect for a couple's getaway, girls’ weekend or just a space to be on your own. Located on a quiet road, close to beaches, walking trails, fishing harbour, restaurants, wineries & breweries. Well behaved dogs are welcomed. Renters must be over the age of 30. Annual Family Pass to Point Peele National Park is available for all guests to use.

4.94 out of 5 average rating, 151 reviews

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

Aerial view of a lakeside property features multiple beach homes along the water's edge. Green kayaks rest near the shoreline, alongside lounge chairs arranged on the beach. The surrounding trees provide shade, while a pathway leads to the welcoming facades of the houses.

4.9 out of 5 average rating, 106 reviews

Hot Tub, Sunsets and Moon lit Lakehouse!

On the pristine waters of Lake Erie, you will find this stunning lakefront escape and pure perfection!! Casa del Lago provides serenity on the shores of one of Ontario's Great lakes... Lake Erie. This contemporary home with its coastal décor, is one of Leamington's most premiere private beachfront home with very spacious living area over two floors, Accommodates 8, has 3 Bedrooms, 2 full Bathrooms and a HOT TUB!

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Popular amenities for Windsor vacation rentals

Laptop-friendly workspace

Stay near Windsor's top sights

Little Caesars Arena159 locals recommend

Ford Field164 locals recommend

Detroit Institute of Arts532 locals recommend

Belle Isle380 locals recommend

Belle Isle Beach388 locals recommend

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

4.86 out of 5 average rating, 137 reviews

The exterior of the home features a welcoming front porch shaded by mature trees. A small table and chairs are placed on the porch, surrounded by greenery. The façade includes light-colored siding with dark trim, enhancing the property's charm.

Home in Ferndale

Welcome home! Short walk to downtown Ferndale

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

4.85 out of 5 average rating, 20 reviews

A spacious bedroom features a king mattress dressed in a white coverlet and decorative pillows. Natural light filters through a window with light-colored blinds. A small wooden side table is positioned nearby, and a patterned area rug covers the hardwood floor.

Home in Ferndale

Upstairs townhouse; king bed, comfortable space.

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

4.89 out of 5 average rating, 122 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

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

4.79 out of 5 average rating, 38 reviews

A circular gravel setting features red Adirondack chairs arranged around a fire pit, facing the serene waters of the lake. Scenic views of the lake's surface and sky are visible in the background, with landscaped stones and minimal greenery enhancing the space.

Home in Leamington

Lakehouse Getaway. Point Pelee

4.78 out of 5 average rating, 9 reviews

The modern kitchen features white cabinetry and a sleek gray countertop. Stainless steel appliances, including a refrigerator and oven, provide functionality. Recessed lighting highlights the open layout, while a doorway leads to the entrance, allowing natural light to flow into the space.

Home in Windsor

"Your Home Away from Home"

5 out of 5 average rating, 3 reviews

A well-lit living area features tiled flooring and smooth walls painted in warm tones. A console table is positioned near the entrance, accompanied by decorative plants. A staircase is visible, leading to an upper level, while a cozy seating area is arranged with a couch.

Home in Detroit

My home, your home

Top guest favorite

A cozy living space features a large television mounted on the wall, framed by soft lighting. Two plush sofas are positioned to face the TV, with a stylish coffee table in the center. A dining area with a light-colored table and chairs is visible in the background, complemented by decorative artwork.

Home in Allen Park

5 out of 5 average rating, 32 reviews

This is your comfortable "home away from home"!

4.93 out of 5 average rating, 69 reviews

An open living area features a cozy chair and a matching ottoman beside a small wooden table. The kitchen, with dark cabinetry, is visible in the background, while a bar area with high stools invites casual dining. Natural light floods through the large windows.

Cottage in Lakeshore

Cottage in Lighthouse Cove with Canal Docking