Vacation rentals in Windsor

4.95 out of 5 average rating, 289 reviews

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.

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.

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, 125 reviews

A well-lit bedroom features a queen-sized bed adorned with a textured blanket and decorative pillows. Soft wall colors complement the modern lighting fixture. A window offers a view of the outdoors, while a piece of wall art adds a touch of color.

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.

5 out of 5 average rating, 120 reviews

A spacious bed is adorned with a floral-patterned comforter in shades of yellow and gray. A small decorative pillow adds a touch of comfort. Natural light filters through two windows, illuminating the cozy seating area nearby, which features a chair with dark stripes.

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.

4.87 out of 5 average rating, 181 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, 716 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, 124 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

4.93 out of 5 average rating, 103 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

Labelle Lodge invites you to this bright home with 2 spacious bedrooms and a living area with high ceilings and tons of natural light. Nestled amongst majestic trees, the serene getaway is just 7 minutes away from the US border. Conveniently located near EC Row, you’re minutes away from the Riverside and the entertainment district. Enjoy high speed internet and two smart TVs with all your streaming apps. Indulge in the outdoor dining area and experience the tranquility of South Windsor.

5 out of 5 average rating, 232 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.

4.94 out of 5 average rating, 106 reviews

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.

Apartment in Walkerville

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.

4.93 out of 5 average rating, 181 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 Walkerville

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, 108 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!

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, 276 reviews

A bright living area features a blue sectional sofa positioned beside a modern, round coffee table. Natural light enters through large windows, illuminating the space. A sleek fireplace and a mounted television are visible along the white brick wall, creating a cozy gathering spot.

Home in Walkerville

Walkerville Charm Home

4.89 out of 5 average rating, 232 reviews

A Spacious Escape: Pool Table, Patio & Big Kitchen

4.86 out of 5 average rating, 159 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

4.95 out of 5 average rating, 140 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 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.

4.99 out of 5 average rating, 72 reviews

The Whimsical Inn

5 out of 5 average rating, 5 reviews

Adorable 2 Bedrooms Unit Near Riverside

4.85 out of 5 average rating, 149 reviews

An outdoor space is defined by a wooden gazebo containing a hot tub, surrounded by greenery from hanging ferns. A small table and adirondack chairs are positioned nearby on a paved area, providing a comfortable spot for relaxation.

Home in Walkerville

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

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, 153 reviews

Full house - 5 bed, 2 bath

Other great vacation rentals in Windsor

4.85 out of 5 average rating, 52 reviews

Apartment in Windsor

Spacious 1BD Apartment | Prime Location | Parking

5 out of 5 average rating, 41 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

4.94 out of 5 average rating, 104 reviews

The loft showcases an open living space with warm wooden floors and a cozy sofa. A stylish chandelier hangs above the kitchen area, which features wooden cabinetry and colorful tile accents. A kitchen island is positioned near the seating area, providing an inviting space for dining or working.

Loft in Walkerville

OldeWalkerville Loft Gem on the River

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, 20 reviews

Spacious 3-Bed Home in S windsor

Apartment in Downtown Windsor

The studio unit features a clean, comfortable queen bed with light-colored bedding. A cozy seating area includes a dark chaise lounge and a wooden table with a chair. The kitchenette displays a sink, stove, and microwave, while large windows provide natural light, framed by sheer and decorative curtains.

4.68 out of 5 average rating, 216 reviews

AKSUM- Location! Lovely Studio, Ensuite Shower, AC

4.86 out of 5 average rating, 86 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!

4.96 out of 5 average rating, 80 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 Walkerville

Cozy Downtown Walkerville Home