Vacation rentals in Windsor

4.9 out of 5 average rating, 292 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, 106 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, 105 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, 213 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, 149 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, 241 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, 112 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, 125 reviews

An outdoor space is sheltered by a cedar gazebo, featuring a hot tub and a compact seating area with two chairs. A barbecue grill is positioned nearby, surrounded by wooden fencing with potted plants adding greenery to the setting.

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.

Condo in Grosse Pointe Park

A three-story building is presented with a white brick facade and prominent archways. Large arched windows frame the entrance, leading to a set of steps. Flanking the entrance, potted plants enhance the welcoming aspect of the property, complemented by well-maintained landscaping.

4.84 out of 5 average rating, 101 reviews

★★Grosse Pointe Retreat★ ★Downtown Detroit Close★

•10-15 mins (7 miles to downtown Detroit) • Great neighborhood specialty market kiddy corner from entrance! • 55" TV w Netflix + Roku • Onsite dedicated parking • Onsite washer + dryer • Central air and furnace • Business Desk • Fully equipped + stocked kitchen • Extremely safe neighborhood • Digital Keys • High Speed Internet • High End Décor • Close to Hill, Village, and Park Grosse Pointe downtowns • 9ft Ceilings • Outdoor Porch • New Everything! • High End Mattresses

4.94 out of 5 average rating, 152 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

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Windsor vacation rentals

Laptop-friendly workspace

Stay near Windsor's top sights

Little Caesars Arena136 locals recommend

Ford Field120 locals recommend

Detroit Institute of Arts195 locals recommend

Belle Isle150 locals recommend

Belle Isle Beach388 locals recommend

Eastern Market66 locals recommend

House rentals in Windsor

4.85 out of 5 average rating, 135 reviews

A modern kitchen space features a large island with wooden stool seating and a light-colored countertop. A designated dining area with a wooden table and chairs is visible in the background, complemented by decorative vase arrangements and soft natural lighting from nearby windows.

Home in The Core

3 Bed Bright Modern Home in Heart of Walkerville

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.

4.97 out of 5 average rating, 191 reviews

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

4.88 out of 5 average rating, 120 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

4.88 out of 5 average rating, 128 reviews

An open living area is featured, showcasing a dining table with black chairs and a modern design. A corner sectional sofa and large wall-mounted TV are visible. Light-colored walls and a wood-like floor create a seamless flow between the spaces.

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

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.

4.9 out of 5 average rating, 125 reviews

Full house - 5 bed, 2 bath

A well-appointed bedroom features a wooden sleigh bed adorned with decorative cushions. Two bedside lamps provide soft illumination on matching nightstands. A patterned area rug lies on the warm-toned wooden floor, adding comfort and style to the space.

4.88 out of 5 average rating, 41 reviews

Full house, 3 BDR, 2WR, free Parking , extra beds

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Other great vacation rentals in Windsor

4.98 out of 5 average rating, 104 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, 80 reviews

A spacious lakefront house features a large patio with bright green chairs and a deck above overlooking the water. A wooden walkway extends from the house to the shoreline, where gentle waves lap against the rocks. Trees provide a natural backdrop, enhancing the private setting.

Home in Amherstburg

Erie View Lakehouse - Serene and Spacious

4.98 out of 5 average rating, 41 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, 9 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

A cozy basement living area features two upholstered chairs positioned around a small black table. The walls are painted in a soft tone, creating a relaxing environment, while a doorway leads to a spacious bedroom with a large bed and modern decor.

Home in Riverside

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

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.