Vacation rentals in Windsor

4.95 out of 5 average rating, 265 reviews

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.

Apartment in The Core

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.

A living room is displayed with a large television featuring a colorful graphic promoting an IPTV service. A remote control rests on a coffee table. Soft lighting from lamps enhances the warm atmosphere, while a cozy seating arrangement invites relaxation.

4.86 out of 5 average rating, 140 reviews

Hot Tub, TV & Sound bar with fire pit to enjoy.

Adults enjoy a shared hot tub outdoor TV, sound bar & fire pit, while the kids enjoy PAC-MAN, popcorn maker & assortment of game boards. Refreshed 2 bedroom with custom kitchen. Upstairs bedrooms offer individual climate control, queen beds. Island kitchen with attached living room. 2 Smart TV’s & unlimited fiber Internet. Ice maker, washer dryer. UNIT B parking in front of right garage off Shepherd, street parking free. BBQ. This is a multi unit home. Hot Tub & backyard are shared with Unit C.

4.97 out of 5 average rating, 106 reviews

A private outdoor patio is enclosed by wooden fencing, featuring a hot tub surrounded by a stone deck. Comfortable seating is provided by minimalist furniture, including a pair of lounge chairs and a small table. Decorative elements, such as a potted plant, enhance the inviting space.

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

4.81 out of 5 average rating, 181 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!

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.

4.94 out of 5 average rating, 158 reviews

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, 106 reviews

A jet ski is parked on a trailer, showcasing sleek black and white design elements with green accents. The vehicle is positioned on a paved drive, with vibrant flowers and greenery visible in the background. Large windows of the residence provide a glimpse of the indoor space.

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.

4.98 out of 5 average rating, 214 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.

4.9 out of 5 average rating, 185 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.

4.92 out of 5 average rating, 374 reviews

Guest suite in Windsor

Lakeshore Hidden Oasis (heated pool / jacuzzi)

Located in Lakeshore, minutes from Windsor / Detroit, a perfect oasis for the couple looking for a quiet escape. The suite's private jacuzzi tub makes it the ideal place in any season! The suite is fully equipped, including a complete kitchenette, Smart TV, etc. A private BBQ is at your door. During your stay you will have access, day and night, to our heated salt water pool. It is open from mid March to early November at 32°C (90°F). The hot tub is open year round.

A modern kitchen features white cabinetry and stainless steel appliances, including an oven and refrigerator. A dining area with a grey table is set with plates and glasses. A hallway leads to the bedrooms, while natural light brightens the space through a nearby window.

4.91 out of 5 average rating, 183 reviews

Downtown 2 Bed 1 Bath Unit w/ Free Parking

Welcome to our updated 2 bed 1 bath upper unit in downtown Windsor! With a fully equipped kitchen including stainless steel appliances & quartz countertops and a 65in TV with Netflix in the living room, this apartment has everything you need for a comfortable stay. Located near transit, shopping, and restaurants. This location is on a quiet block just minutes walk to the heart of downtown. Book now for a cozy and convenient home-away-from-home experience!

4.99 out of 5 average rating, 175 reviews

A modern kitchen features quartz countertops and stainless steel appliances, including a spacious refrigerator and gas stove. An island with seating is situated in the center, while an open design connects to the cozy living area, creating a welcoming and functional space.

Farm stay in Essex

Luxury Farm Stay - Hot tub - Allow pets - Firepits

-Breathe in the presence of nature- You will quickly fall in love with the quiet pace, beautiful nature, and fabulous food and wine on County Road 50. This luxurious cottage hideaway is surrounded by wildlife and farmland. Private access to idyllic grounds that span over 225 acres of farmland, creeks, and with frontage onto majestic Lake Erie. Bathe in our farm and forests' healing power. Town of Essex License #STR-2022-28

A well-lit staircase features wooden steps leading up, flanked by a black railing with decorative spindles. A potted plant sits on a ledge at the top, and natural light filters in through a window, enhancing the clean and inviting space.

4.94 out of 5 average rating, 147 reviews

"The Oasis" a Walkerville dream / 2 Bed - 1 Bath

Kick back and relax in this calm, stylish space. This uniquely renovated century home is located in the heart of Old Walkerville and is just a few steps from all the beauty this area 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 Arts200 locals recommend

Eastern Market72 locals recommend

Campus Martius Park District132 locals recommend

Motown Museum139 locals recommend

House rentals in Windsor

4.97 out of 5 average rating, 194 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

4.95 out of 5 average rating, 127 reviews

The kitchen features a large island with modern seating, complemented by sleek cabinetry and stainless steel appliances. A brick accent wall adds texture, while natural light floods the space through a nearby window overlooking the quiet neighborhood.

Home in Riverside

Windsor Castle is Waiting for You

A well-lit sleeping area features a spacious bed with crisp white linens and decorative pillows. Two soft-lit lamps illuminate the bedside, and green plants add a natural touch. A serene artwork hangs above the bed, depicting a boat against a tranquil background.

4.93 out of 5 average rating, 67 reviews

Cheerful & cozy downtown 2-bedroom home

5 out of 5 average rating, 58 reviews

A spacious backyard is surrounded by greenery and trees, featuring a cozy seating area under a gazebo. A fire pit is situated next to a wooden bench, inviting outdoor gatherings. The house's exterior displays a combination of wood and modern finishes, creating an inviting atmosphere.

Home in LaSalle

Turkey Creek Hideaway

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.

4.87 out of 5 average rating, 133 reviews

Beautiful 3Bedroom 2Bath Home free parking&laundry

5 out of 5 average rating, 100 reviews

A well-maintained putting green is showcased in a spacious backyard, surrounded by lush greenery and decorative string lights illuminating the area. A cozy fire pit area is visible, along with a wooden shed, creating a relaxed outdoor atmosphere ideal for gatherings.

Home in Kingsville

Stylish Getaway steps to DT Kingsville, Spa & Lake

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.

4.88 out of 5 average rating, 40 reviews

Stylish Apt Near Downtown- Ideal for Long Stays!

4.75 out of 5 average rating, 111 reviews

A modern living area features a light gray sectional sofa paired with decorative pillows. A round wooden coffee table is positioned in front, while a wall-mounted TV and shelving with plants add visual interest. Natural light enters through stylish window treatments.

Home in Windsor

stylish house in south windsor-2 bedrooms

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Other great vacation rentals in Windsor

4.97 out of 5 average rating, 32 reviews

A vibrant neon sign displaying 'The Bitcoin Building' is prominently featured above the entrance. The signage is illuminated in orange, contrasting with the cool blue tones of the building’s windows, highlighting the modern architecture of the property.

Apartment in The Core

Farmer's Market, Balcony, 24/7 Gym, IPTV

A view into a spacious bedroom showcases a handcrafted built-in queen bed framed by large windows, allowing natural light to illuminate the room. Decorative antique-style lighting fixtures hang above, complemented by intricate glass details on the door. Polished hardwood floors reflect the warm tones of the interior.

4.96 out of 5 average rating, 46 reviews

Boutique Suite on the River

5 out of 5 average rating, 29 reviews

An open game room features a ping pong table centrally located on a light wood floor. Soft lighting enhances the space, which includes a casual seating area with two armchairs and a small table. A staircase leads to other levels of the home.

Home in South Windsor

South Windsor Luxury Home - Private Gym/Sauna

5 out of 5 average rating, 91 reviews

A modern lower-level space features an open dining area with a dark wooden table surrounded by light chairs. A writing desk with a chair is positioned nearby. Recessed lighting brightens the area, with muted wall art adding a subtle touch to the neutral surroundings.

Home in Windsor

Luxurious 3BR, King Bed, Ensuite. Perfect Stay!

4.88 out of 5 average rating, 16 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)

4.76 out of 5 average rating, 42 reviews

A contemporary kitchen features dark cabinetry and a spacious wooden countertop. Appliances include a microwave, oven, stovetop, and coffee maker. A wooden dining chair is positioned at the counter, while gray tiles cover the floor, providing a clean and functional cooking space.

Bungalow in Windsor

One bed room house with one Qween bed

4.88 out of 5 average rating, 43 reviews

A narrow hallway is depicted, featuring three small mirrors on a white wall. At the end of the hallway, a dining area is highlighted with a round table and two chairs, accompanied by a modern artwork and a tall indoor plant.

Apartment in Windsor

Rare find by the Riverside