Vacation rentals in Windsor

The exterior of the two-story property features light blue siding and a decorative gabled roof. A covered porch with a white railing and steps leads to the entrance. A wooden gate is visible to the side, providing access to the backyard.

4.95 out of 5 average rating, 287 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.

4.9 out of 5 average rating, 268 reviews

A spacious wooden deck extends towards Lake Erie, featuring a grill and two outdoor chairs. The gentle waves can be seen lapping against the rocky shoreline. Lush greenery frames the scene, adding a natural touch to the outdoor space.

Cottage in Kingsville

Lakeview Inn

The Lakeview Inn sits on the North Shore of beautiful Lake Erie. This modern lakehouse is an 8 minute drive to the centre of kingsville where there is multiple breweries and restaurants, a public beach is a 1 minute drive down the road and is right in the centre of Southern Ontario's Wine Country. If you're coming down for a weekend to relax, taste wine or to enjoy the exceptional birding the area has to offer. At the end of your day relax to the sound of the waves brushing up against the shore.

4.98 out of 5 average rating, 121 reviews

A spacious open concept living area is presented, featuring a comfortable seating arrangement with leather couches and a glass coffee table. A modern kitchen showcases stainless steel appliances and dark cabinetry, while a rug adds warmth to the light-toned floor. Natural light fills the space.

Guest suite in Windsor

Serenity by the Woods- Elegance with Amenities

Welcome to our secluded and private lower level apartment backing onto a forest. A deer family frequently visits the backyard. We strive to make guests feel at home with tasteful decor & thoughtful amenities. The suite is especially suited to business travelers & small families. Location is central, with 3, 6 & 8 min drives to the grocery store, Walmart and Ambassador bridge. * We are in Canada. You have a fully private floor to yourself, but this is not the full house—we live upstairs.

4.89 out of 5 average rating, 177 reviews

A spacious living area features a comfortable gray sectional sofa adorned with decorative cushions. A wooden coffee table is centered on a soft area rug, while a wall-mounted television and a small dining table for two are visible. Natural light enters through large windows.

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!

4.98 out of 5 average rating, 708 reviews

A lake house is situated on the shoreline of Lake Erie, featuring a sloped path with steps leading down to it. Soft lights illuminate the exterior during twilight, creating a warm ambiance. The tranquil water extends to the horizon, inviting a peaceful retreat.

Guesthouse in Kingsville

Small lake house on Lake Erie shore

Private Bachelor apartment sized house directly on Lake Erie. ULTRA FAST WI-FI, Private deck, Kayaks. The Cottage is always toasty warm all winter long. Queen bed, bathroom with shower, kitchenette. Great swimming in shallow, sandy waters. Cottage is only a few minutes from many area wineries, breweries, distilleries and fantastic restaurants serving local food. Walking distance to Pelee Island ferry. Want something completely different? This is the place. It's almost like staying on a boat.

4.97 out of 5 average rating, 120 reviews

A private outdoor patio features a hot tub surrounded by wooden fencing and a pergola. Comfortable seating is provided by two chairs, with a BBQ grill situated nearby. Natural light filters in through the overhead structure, enhancing the relaxing atmosphere.

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

5 out of 5 average rating, 225 reviews

A bright living space is presented with large windows offering stunning lake views. Comfortable seating is arranged around a central coffee table. A dining table for four is positioned nearby, with decorative accents complementing the airy atmosphere. Light floods the room, enhancing its open feel.

Cottage in Essex

The Kiss nTell - Year round - Hot tub - Lake Views

If you “glamp” when you camp, then you’ll appreciate the finer amenities of this boutique style cottage on Lake Erie. Arguably the best views in this tiny cottage community, The Kiss n Tell graces a bluff overlooking the lake - stunning views from every room. Wake to the sound of waves crashing the shore, sunbathe in loungers, dine while the sun glistens on the water, star gaze from the hot tub or sit by a lakeside fire (firewood provided). Endless options w/out leaving this beautiful space.

A living area is presented with a dark, plush sofa and a low coffee table situated on a textured area rug. A round mirror decorates the wall, reflecting light. A doorway leads to a bedroom space, while a small dining area with bar stools is visible to the side.

4.94 out of 5 average rating, 104 reviews

Walkerville Loft (Main floor unit)

Welcome to our charming loft nestled in the heart of a Walkerville in Windsor. This thoughtfully designed space combines modern comfort with historical charm. Perfect for couples or solo travelers, our cozy loft features fire place, high ceilings, and large windows. Enjoy the convenience of being centrally located, with iconic landmarks, local shops, and vibrant cafes just steps away. Immerse yourself in the city's rich history during the day and unwind in this stylish retreat at night.

4.94 out of 5 average rating, 177 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.

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.

4.99 out of 5 average rating, 104 reviews

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

Welcome to our 2 year old, modern and bright 3-bedroom, 3-bathroom townhome in East Windsor! Our home features a spacious layout with a clean and contemporary design, making it the perfect spot for your next getaway. The king-sized bed in the master bedroom comes with an ensuite bathroom for added privacy and convenience. Great location, close to WFCU Centre. Perfect for family vacations, weekend getaways, or business trips. Experience the best of East Windsor from our cozy home!

4.88 out of 5 average rating, 196 reviews

A serene view of the river is framed by trees with autumn foliage. The peaceful water reflects the clear sky, while tall grasses and reeds line the riverbank. A wooden fence and steps are visible in the foreground, leading to the water's edge.

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 dining area is highlighted by a wooden table accompanied by four blue upholstered chairs. A minimalist aesthetic is enhanced by a potted plant and wall art featuring colorful portraits. Natural light enters through a window covered by a blind.

4.96 out of 5 average rating, 139 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

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

Monthly stays

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Windsor's top sights

Little Caesars Arena303 locals recommend

Ford Field294 locals recommend

Detroit Institute of Arts746 locals recommend

Eastern Market369 locals recommend

Campus Martius Park District320 locals recommend

Motown Museum388 locals recommend

Windsor house rentals

4.83 out of 5 average rating, 153 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 living room is shown with light-colored walls and hardwood flooring. A beige sofa is positioned in the center, with two patterned yellow chairs flanking a simple wooden coffee table. A framed artwork with a floral design hangs above the sofa, and greenery is visible from a nearby window.

5 out of 5 average rating, 16 reviews

Spacious 3-Bed Home in S windsor

4.95 out of 5 average rating, 21 reviews

A spacious living room features a large sectional couch and a coffee table, with a television displaying a beach scene. Bright natural light enters through the window, which is complemented by light curtains. The polished wooden floor adds warmth to the space.

Home in Riverside

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

A bright living room features two modern sofas facing a coffee table, with a large window dressed in sheer curtains allowing natural light. A functional bar area with stools is visible in the background, connecting to the kitchen, while light wood flooring enhances the space.

4.95 out of 5 average rating, 111 reviews

3BR Home Near Downtown w/ 5 Beds & Finished Basmnt

A modern living area features a gray sectional sofa positioned in front of a low black table. The wall is adorned with a piece of abstract art. Light-colored walls and a doorway leading to another room enhance the spacious feel, complemented by plush carpeting.

4.76 out of 5 average rating, 46 reviews

Brand new basement- Entire place

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.

4.87 out of 5 average rating, 149 reviews

Full house - 5 bed, 2 bath

4.91 out of 5 average rating, 115 reviews

The exterior of a two-story brick home features large windows framed by wooden shutters. A stone pathway leads to the entrance steps, which are flanked by neatly landscaped flower beds and ornamental plants in decorative pots. The entrance is inviting, with a warm color palette.

Home in LaSalle

The Ambassador Estate Inn

4.95 out of 5 average rating, 100 reviews

A comfortable living room area is shown, featuring a gray sectional sofa and a blue armchair. A round wooden coffee table sits on a decorative rug, while a flat-screen TV is mounted on the wall. Soft lighting enhances the inviting atmosphere.

Home in Belle River

little cozy house 2 bedroom

Other great vacation rentals in Windsor

The kitchen features light blue cabinetry, a stainless steel stove, and a spacious fridge. A glass dining table with wooden chairs is positioned in the center. Natural light enters through a large window, brightening the tiled floor and enhancing the area.

4.76 out of 5 average rating, 71 reviews

Gusii- Main Floor, Central Spot, Full 1BR APT, AC

5 out of 5 average rating, 38 reviews

A modern kitchen features light wood cabinetry and a spacious island with seating for four. Pendant lights hang above the counter, illuminating the area. Stainless steel appliances, including a refrigerator and oven, are visible, while the open layout extends into a bright living space with large windows.

Home in South Windsor

South Windsor Luxury Home - Private Gym/Sauna

4.84 out of 5 average rating, 58 reviews

A modern living area features a plush orange sofa facing a wall-mounted television. Natural light enters through large windows, which are framed by light grey curtains. A neutral-toned area rug lies beneath a coffee table, enhancing the spacious feel of the room.

Apartment in Windsor

Rare find by the Riverside

5 out of 5 average rating, 4 reviews

Adorable 2 Bedrooms Unit Near Riverside

5 out of 5 average rating, 36 reviews

A modern two-story home displays a light grey façade with a distinct peaked roof. A large central entrance is framed by elegant stone accents. A vehicle is parked in the driveway, while the surrounding area features unlandscaped grounds and nearby homes, enhancing the neighborhood feel.

Home in Riverside

Happy Trails Inn

4.9 out of 5 average rating, 81 reviews

A private guest suite features a spacious bed with a dark blue coverlet, a cozy sofa, and a TV mounted on the wall. Natural light enters through large sliding doors, complemented by dark blue curtains. A small round table stands nearby, adding to the inviting atmosphere.

Guest suite in Windsor

Private/Quiet Perfect for professionals!

4.97 out of 5 average rating, 76 reviews

A cozy living area features a light-colored sectional sofa adorned with patterned pillows. A modern glass coffee table sits in the center, complemented by a decorative plant on the side. Exposed brick walls add texture, while a window with an arch design enhances natural light.

Townhouse in The Core

Cozy Downtown Walkerville Home