Vacation rentals in Windsor

The entryway features a decorative staircase leading to the upper unit. A stained glass window adds a splash of color, complemented by a blue vase containing dried branches. A candle on a slender stand enhances the welcoming atmosphere, while a textured rug lies at the base of the steps.

4.95 out of 5 average rating, 269 reviews

OLDE WALKERVILLE, Windsor, Ontario

Do you need a nice quite, non-shared clean place to stay ? This cute one bedroom, living room /sleeper sofa, kitchen, full bath (washer/dryer 6 nights + ) Located on the second floor, above our family home, is ready for you to enjoy your stay. In Olde Walkerville, walking distance to restaurants, pubs, boutiques and, the river with walking and bike paths along with summer activities. Short drive to the Casino, Chrysler Theatre / St. Clair Arts, U.S.A Boarder, down town Train Station.

5 out of 5 average rating, 114 reviews

Guest suite in Riverside

Ray's iNN Olde Riverside (all private)

PRIVATE GUEST SUITE with OWN ENTRANCE. Boutique Hotel Suite inspired,offering amenities,privacy & charm.50”Samsung TV+Netflix.This Suite has a KITCHENETTE with SINK also mini-fridge,microwave,toaster-oven,slow-cooker, cooktop,coffee maker,kettle.PRIVATE BATHROOM with stand up shower.Includes dishes, glassware,utensils, towels,linens,coffee.Seasonal PATIO & lovely landscaping. Within Olde Riverside,close to shops,restaurants,grocery,parks, WFCU Centre.Short walk to a beautiful riverfront & trail.

4.89 out of 5 average rating, 158 reviews

The exterior of a spacious one-story house is featured, showcasing a brick façade and a prominent entrance with large windows. A driveway leads to a garage, with a parked car positioned comfortably in front. The surrounding lawn is well-maintained and offers a clear view of neighboring homes.

Apartment in Windsor

Private Luxury 1BR Retreat in Prime Location

Luxurious 1BR Retreat Prime Location, Perfect for Your Getaway! Escape to this stunning one-bedroom haven in LaSalle, where comfort and convenience meet! Whether you're here for a romantic getaway, a solo retreat, or a business trip, this modern sanctuary has everything you need for a perfect stay. Whether you're here for business or leisure, this luxurious one-bedroom retreat is the perfect home base for your LaSalle getaway. Book now and experience all the comfort and convenience you deserve!

4.97 out of 5 average rating, 108 reviews

Home in Riverside

Perfect hideaway with a hot tub and a fireplace

Find your sanctuary at Little River Retreat. Bordering parks, with luxe vibes, a crackling fireplace, and a dreamy hot tub. Enjoy a walk or bike ride through beautiful parks and beaches, including the 10 km+ Ganatchio Trail and Sandpoint Beach (both 5 minutes away). In under 45 min, find yourself in wine country, or for nature lovers, Point Pelee National Park. WFCU Centre 3 min away. Caesars Windsor, tunnel & bridge to USA 10-15 min away. Detroit airport approx 45 min, new battery plant 9 min

4.94 out of 5 average rating, 388 reviews

A chiminea is positioned on a grassy area overlooking the lake, providing a unique focal point against the backdrop of clear blue waters. Gentle waves can be seen in the distance, and leafy trees frame the scene, contributing to a sense of tranquility.

Cottage in Essex

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! ♥️

4.8 out of 5 average rating, 182 reviews

Home in Riverside

Beautiful Oasis w/Heated Private Pool & Sunroom!

*HEATED POOL IS OPEN APRIL 1 - OCT 31* Welcome to Windsor’s largest and coziest stay! This gorgeous home blends modern design with comfort, featuring an inviting sunroom with soaring ceilings and natural light, perfect for morning coffee or quiet evenings. The chic decor creates a stylish, yet homey feel :) Unwind in a private backyard oasis with a 15x30, 8’ deep, in-ground oval pool with a brand NEW heater and BBQ lounge! Our backyard designed for a unique and relaxing family experience!

4.94 out of 5 average rating, 163 reviews

A modern living area is featured, furnished with a soft gray sofa and a stylish coffee table. A wooden sideboard is placed against the wall, complemented by decorative items. Light walls enhance the spacious feel, while a chandelier adds subtle brightness to the room.

Home in The Core

Charming Old Walkerville 2-Bedroom Luxury Suite

Located in the heart of Old Walkerville. Steps from restaurants, bars, shops, parks and the waterfront. A bright and comfortable main level suite that's part of a large duplex home. Perfect for relaxing visitors or working professionals. There are two spacious bedrooms with queen beds, closet and drawer storage. The grand room and kitchen are fully equipped just like home. The deck and yard space are available for fresh air fun and entertainment. There are 2 parking spots on site.

4.92 out of 5 average rating, 107 reviews

A landscaped outdoor area showcases a serene pool surrounded by lush greenery and decorative rocks. A pathway of stone pavers leads to a shaded seating area with an outdoor gazebo. Vibrant fall foliage frames the scene, adding warm color to the tranquil setting.

Home in LaSalle

The Ambassador Estate Inn

A warm “welcome back” to all our previous guests and “greetings” to our new friends! A luxurious executive 7 bedroom estate property located on Windsor’s finest golf course and minutes from the Ambassador Bridge to Detroit Michigan. A beautifully appointed home nestled among rare Carolinian Forest. All the amenities of a 5 star resort with the privacy and serenity of a country estate. If you are looking for quality and relaxing luxury, then look no further than the Ambassador Estate.

4.78 out of 5 average rating, 155 reviews

A shaded outdoor seating area is shown, featuring a green cushioned loveseat, a small dark table, and two additional chairs. Potted plants add greenery to the wooden deck space, while a privacy screen of wooden slats surrounds the area.

Cottage in Essex

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

4.98 out of 5 average rating, 215 reviews

An outdoor seating area is presented, featuring two light-colored armchairs positioned around a small black table with a decorative top. The entrance is framed by double doors with glass panes, and a brick wall enhances the rustic charm of the space.

Guest suite in Riverside

Glenn & Deb’s Place

1100 sq. ft guest suite attached to main residence but completely separate space on quiet residential street. Upper level with two bedrooms, washer/dryer and 1 bathroom with custom shower. Lower level has full kitchen, living room with gas fireplace, 42'' television and high speed internet. Independent heating and cooling. Owners are on site for quick response to all your needs. Close to WFCU, Caesars Windsor and all major arteries. We regret we are unable to accommodate pets.

4.89 out of 5 average rating, 186 reviews

A serene backyard is presented, featuring lush green grass and shade from large trees. Two vibrant lounge chairs are positioned near a gently flowing river, visible in the background. Additional seating areas and a patio umbrella are also included, enhancing the outdoor space.

Villa in Windsor

4 Bedroom Waterfront Oasis Getaway with Hot Tub

Located by the river, a 5 minute drive from the shopping center. This 4-bedroom home is equipped with fully furnished living and dining areas, as well as a backyard spot perfect for fishing, boating, canoeing, and winter ice skating. The yard, among the river, features a fire pit, a tree swing, and multiple sitting areas. You will enjoy traveling downstream by boat into the Detroit River bay, or taking a short drive to nearby attractions, shopping areas, and local restaurants.

A modern bathroom sink area features a sleek white countertop paired with a black towel bar. A circular mirror reflects light above the sink. A potted plant adds a touch of greenery, while a colorful wall art piece enhances the overall visual appeal.

4.96 out of 5 average rating, 131 reviews

"The Modern Loft" in Walkerville / 2Bed - 1 Bath

Enjoy a luxury modern experience in the heart of Old Walkerville. This modern 2 bedroom loft is newly renovated with luxury finishes while keeping century old details. Restaurants, pubs, cafes, retail all within a minute walk from this superb location. Stay here and get a taste of what Old Walkerville has to offer. DISTANCES TO: Casino - 2 minutes Downtown - 2 minutes Hospital - 5 minutes Detroit - 10 minutes Ford Field - 12 minutes Little Ceasers Arena - 12 minutes

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

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Windsor's top sights

Little Caesars Arena140 locals recommend

Ford Field124 locals recommend

Detroit Institute of Arts203 locals recommend

Eastern Market72 locals recommend

Campus Martius Park District133 locals recommend

Motown Museum140 locals recommend

House rentals in Windsor

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, 196 reviews

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

4.85 out of 5 average rating, 263 reviews

A covered porch features a smooth concrete floor and brick walls. Two comfortable chairs are arranged near the entry, along with a small wooden table. Natural light filters through the nearby windows, and a gently sloped ceiling adds architectural interest.

Home in The Core

Walkerville Charm Home

4.86 out of 5 average rating, 154 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

4.99 out of 5 average rating, 215 reviews

A comfortable living area features a stylish orange sofa and gray armchair, centered around a round area rug with a modern pattern. Natural light enters through two windows, highlighting a wooden coffee table decorated with a small plant and decorative items. A floor lamp stands nearby.

Home in Ferndale

Little Yellow House in Ferndale! Quiet, Cozy 3BR

4.88 out of 5 average rating, 41 reviews

A cozy living room is presented, featuring a modern leather sofa and a minimalist coffee table on a natural fiber rug. A floor lamp and potted plant add warmth, while light filters through sheer curtains, enhancing the inviting space.

Home in The Core

Stylish Apt Near Downtown- Ideal for Long Stays!

A living area showcases a modern design with a blue accent wall featuring geometric gold lines. A large smart TV is positioned on a wooden entertainment unit. A glass coffee table is centered in front of the TV, while a tall plant adds a touch of greenery.

4.93 out of 5 average rating, 29 reviews

Comfy dream • 2 beds • Netflix • work desk

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.

4.88 out of 5 average rating, 129 reviews

Full house - 5 bed, 2 bath

A modern kitchen is equipped with sleek white cabinetry and a stainless steel refrigerator. A wooden dining table is set with plates and glasses, with a microwave and coffee maker in the background. The backsplash features a mosaic design adding a contemporary touch.

4.83 out of 5 average rating, 12 reviews

Greetings to all.Specially Battery Plant workers.

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Other great vacation rentals in Windsor

4.84 out of 5 average rating, 32 reviews

A hallway is shown, featuring wooden paneling and a well-lit space. Two doors lead to adjoining rooms, while a view of a bathroom vanity is visible in the background. Hooks are mounted on the wall for convenience, adding to the functional layout.

Guest suite in Windsor

Spacious 1BD Apartment | Prime Location

4.93 out of 5 average rating, 14 reviews

Cottage in Windsor

Spring Garden Suite | Nature | Family | Comfort

4.98 out of 5 average rating, 64 reviews

A wooden ramp leads up to a white door framed by a brick wall. The space is well-lit, showcasing a welcoming entrance. Handrails are present on either side of the steps, offering support. Potted plants are positioned nearby, adding a touch of greenery.

Guesthouse in The Core

Modern guest suite downtown

4.88 out of 5 average rating, 17 reviews

A modern kitchen is featured, showcasing sleek white cabinets and contrasting black countertops. Stainless steel appliances are visible, including a refrigerator and oven. Four high-backed chairs are arranged at the kitchen island, creating a functional space for dining or meal preparation.

Apartment in Windsor

Luxury Unit Windsor (4-plex)

4.97 out of 5 average rating, 72 reviews

A modern kitchen features sleek white cabinetry contrasted by a black tile backsplash. Natural light filters through a window above the stainless steel sink, illuminating the granite countertops. Kitchen appliances, including a refrigerator and stove, are positioned neatly, with organized utensils nearby.

Home in South Windsor

Luxury 2BR home with high ceilings and BBQ w/patio

4.94 out of 5 average rating, 31 reviews

Come and relax at the BlueByU!

The modern bathroom features a glass-enclosed shower and a bathtub. Dark cabinetry complements the light marble walls. A mirror above the sink reflects soft lighting, while towels hang neatly on a rack. Subtle decor accents enhance the minimalist aesthetic.

5 out of 5 average rating, 7 reviews

The Urban Nest - Windsor