Vacation rentals in Windsor

4.95 out of 5 average rating, 266 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 Walkerville

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.

4.89 out of 5 average rating, 151 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, 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, 159 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 Malden

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, 376 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.

4.91 out of 5 average rating, 184 reviews

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.

Home in Downtown Windsor

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!

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, 148 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

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

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

5 out of 5 average rating, 30 reviews

A contemporary living area showcases an open concept design with high ceilings and ample lighting. A dark sofa and beige armchairs are arranged around a wooden coffee table, complemented by decorative accents. A neutral area rug adds warmth to the polished hardwood floor.

Home in South Windsor

South Windsor Luxury Home - Private Gym/Sauna

CathrynRating, 5 stars6 days ago

Thank you for making us feel welcome! We thoroughly enjoyed our stay in your beautifully decorated space. The flowers, snacks, water and slippers were a personal touch. Lots of room to spread out and celebrate with family. The location was perfect for getting around Windsor easily. A peaceful oasis close by everywhere you wanted to go.

An entrance area features original woodwork and stained glass details, contributing to the historical character of the space. Glass block walls allow natural light to enter, while a spacious doorway leads to the bathroom. A glimpse of a cozy living area with a TV is visible beyond.

4.96 out of 5 average rating, 46 reviews

Boutique Suite on the River

SuzanneRating, 5 stars2 weeks ago

We really enjoyed our stay in this home, which has a great location near the waterfront. The house itself is cozy and beautifully decorated, perfectly blending charm with modern amenities. I particularly appreciated the comfortable bed, which ensured restful nights after long walks exploring the waterfront and the town of Walkerville. The host is very attentive and friendly, making us feel welcome. Thank you, Michele! If we come back to Windsor, we would look forward to staying here again! Suzanne & Dave

5 out of 5 average rating, 92 reviews

A modern kitchen features sleek white cabinetry and stainless steel appliances. A quartz island is complemented by a decorative tray with coffee essentials. A wall clock adds a touch of functionality, while a bowl of green apples offers a fresh accent.

Home in Windsor

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

ToshaRating, 5 stars2 days ago

In the beginning we had a small issue, Olivia was responsive and quickly resolved it. I was apprehensive about renting a town home, however I was pleasantly surprised. The home is elegant, spacious and well maintained. The neighborhood is really peaceful, and is in a great location. Olivia and her staff were professional and very friendly. We highly recommend and would stay there again for our future visits.

4.97 out of 5 average rating, 68 reviews

An outdoor dining area is set with a red table and chairs under a retractable awning. The grey exterior of the lodge is framed by a manicured lawn and wooden fencing, creating a secluded and private atmosphere. Natural light enhances the inviting space.

Home in South Windsor

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

MichaelaRating, 5 stars2 days ago

I can’t say enough good thing about this space! From the moment you walk in, the high privacy fence makes you feel right at home. The house itself is flooded with natural light and has high lofty ceilings. Both beds were extremely comfortable—which made the trip all the more better! Oh and our dogs loved being able to travel with us! Highly recommend his space as it was clean, pristine and beautiful.

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

LuisRating, 5 stars2 weeks ago

A perfect stay to relax

5 out of 5 average rating, 8 reviews

Home in Devonshire

Modern & Cozy Home Retreat

RachnaRating, 5 stars1 week ago

We had really great experience. Alin is a great host we got response in 5 to 10mins. Place was clean and had everything we needed. Felt like home.

5 out of 5 average rating, 3 reviews

A spacious living area features two large sofas facing a wooden coffee table, set on a soft rug. High ceilings allow natural light to fill the room. A stone fireplace adds character, while a dining area with multiple chairs is visible in the background.

Home in Tecumseh

S - Stylish 4BR Retreat – Comfort Meets Elegance

TalarishaRating, 5 stars1 week ago

This home is completely beautiful, my family felt right at home! Definitely saved the address for future trips we loved it 😊

5 out of 5 average rating, 7 reviews

A welcoming exterior view of a single-story brick home is presented. The entrance features a set of steps leading to a covered porch, complemented by decorative railings and a tall evergreen shrub nearby. Light flows through the large front window, enhancing the inviting facade.

Home in Riverside

Perfect stay! 4 BDR in East End

JennaRating, 5 stars4 months ago

We had a great stay and the host was very helpful and accommodating! There are many helpful items in the kitchen (blender, Keurig etc) and there were even ice cubes ready in the freezer. Two living spaces to sit (one upstairs and one downstairs) which is nice. There was some construction materials in the back/side yard but we weren’t intending to use the yard anyway, just a visual thing we noticed upon checking in. There was also some drywall opened up around a new electrical panel in the basement which was a bit of an eye sore but didn’t affect our stay at all. I assume that will be re-dry walled soon as it appears like it may be related to the construction happening in the back yard. Overall a cozy stay and would recommend to friends.

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Other great vacation rentals in Windsor

Apartment in Downtown Windsor

A modern open-concept living space is showcased, featuring a sleek kitchen with dark cabinetry and stainless-steel appliances. A glass dining table with beige chairs is positioned adjacent. A spacious light gray couch occupies the corner, while warm wood flooring adds comfort to the area.

4.77 out of 5 average rating, 95 reviews

luxury 2-Bedroom Apartment In Downtown Windsor

NkemRating, 5 stars2 weeks ago

Unfortunately we couldn't find the dishwasher, but everything else was great.

Apartment in Downtown Windsor

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.

4.97 out of 5 average rating, 33 reviews

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

MagRating, 5 stars1 day ago

I recently visited Windsor for a work trip and had a wonderful stay at the Bitcoin Building. Our unit was not only tastefully decorated but also equipped with all the essential items we needed. One of the highlights was the lovely balcony, which added a nice touch to our experience. The location couldn't have been better—just a short distance from Riverside, a variety of restaurants, and the casino. Additionally, Ray's communication was outstanding, making our stay even more enjoyable.

4.84 out of 5 average rating, 31 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

NicoleRating, 5 stars1 week ago

very friendly and accommodating host, her professionalism really stupid very quick to respond had a peaceful stay here would definitely book again 10/10

4.98 out of 5 average rating, 60 reviews

A spacious living area features a comfortable sectional sofa and a decorative coffee bar. Brightly colored artwork and a large light fixture enhance the atmosphere. A vintage popcorn machine and dining table are visible, alongside a view into the kitchen area.

Home in Windsor

The Whimsical Inn

ShawnRating, 5 stars1 month ago

Super responsive, super nice host. Will stay again the next time I'm in town.

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)

MohamedRating, 5 stars2 months ago

Great host, great home! The process was very smooth and we felt right at home.

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

AndrewRating, 5 stars3 weeks ago

The skylight in the kitchen is very cozy, the bed is comfortable, and the bathroom is clean and spacious. The living room is a bit bland though, so I stayed in the kitchen until bed time.

4.94 out of 5 average rating, 31 reviews

Apartment in Walkerville

Come and relax at the BlueByU!

WillRating, 5 stars1 week ago

Truly a wonderful experience staying at BlueByU, the cleanliness and hospitality made it feel like a home away from home. Very peaceful atmosphere as well as the neighbourhood. 10/10!