Vacation rentals in Windsor

4.95 out of 5 average rating, 296 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.

4.91 out of 5 average rating, 275 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.

5 out of 5 average rating, 123 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, 189 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

The Ambassador’s Stay • Bright 1BR Family Retreat

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!

4.85 out of 5 average rating, 101 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!

Discover comfort in this private guest suite w/ self-check-in and a separate entrance, located in the tranquil Southwood Lakes neighborhood. Close to golf courses and Devonshire Mall, it’s perfect for relaxation or exploring nearby amenities. Enjoy a swivel mount TV with Netflix and Amazon Prime from the cozy sofa or bed. Step into the spacious backyard with a stunning gazebo and elegant seating, ideal for unwinding. Luxury bathroom w/ supplies. Coffee bar! Book your peaceful escape today!

4.97 out of 5 average rating, 130 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, 106 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, 240 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.

4.93 out of 5 average rating, 109 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.

4.94 out of 5 average rating, 187 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, 116 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!

4.93 out of 5 average rating, 403 reviews

A serene outdoor space features a salt-water pool surrounded by lush greenery, lounge chairs, and shaded seating areas. Natural stone accents are present near the water's edge, with steps leading up to a covered patio area. Tree silhouettes frame the background, enhancing the tranquil setting.

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.

Popular amenities for Windsor vacation rentals

Monthly stays

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Windsor house rentals

5 out of 5 average rating, 28 reviews

JP's Dream House

4.95 out of 5 average rating, 171 reviews

The two-story green house features a generous front porch with seating and is surrounded by a grassy lawn. A detached garage is visible to the right, framed by landscaping. The overall setting is tranquil, with trees lining the background under an overcast sky.

Home in Essex

Shores of Erie Guest House

4.87 out of 5 average rating, 60 reviews

Spacious 1BD Apartment | Prime Location | Parking

4.83 out of 5 average rating, 279 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, 237 reviews

A Spacious Escape: Pool Table, Patio & Big Kitchen

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.

4.88 out of 5 average rating, 152 reviews

Beautiful 3Bedroom 2Bath Home free parking&laundry

5 out of 5 average rating, 12 reviews

Modern 1 Bedroom Loft in Sandwich Town - Windsor

4.98 out of 5 average rating, 192 reviews

A year-round hot tub is positioned under a wooden pergola, with views of a sunset reflecting on the calm waters of Lake Erie. Adirondack chairs are visible nearby, providing a relaxing spot to enjoy the surrounding natural beauty.

Home in Amherstburg

Lake Erie retreat-unwind & explore local wineries

Other great vacation rentals in Windsor

5 out of 5 average rating, 46 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

Luxury South Windsor Home with Private Gym/Sauna

Apartment in Downtown Windsor

A bright living area features a dark sectional couch adorned with patterned cushions. A glass coffee table sits in front, while a flat-screen TV is mounted on the wall opposite. Large windows offer views of the surroundings and allow natural light to illuminate the space.

4.71 out of 5 average rating, 201 reviews

BORNU-2nd Flr Spacious, Location, Clean, 1BDr, A/C

Guest suite in Downtown Windsor

A cozy bedroom is presented with a wooden headboard and crisp white linens on the spacious bed. A bedside table with a warm lamp offers soft lighting, while white walls create a serene atmosphere.

4.99 out of 5 average rating, 79 reviews

Modern guest suite downtown

4.93 out of 5 average rating, 14 reviews

A stylish living area features a green velvet sofa complemented by a wooden coffee table with intricate detailing. Large windows are draped with green curtains, allowing natural light to enhance the space. A decorative mirror and a floor lamp add character to the room.

Home in Walkerville

Serene Green 2BR Haven in Little Italy

4.96 out of 5 average rating, 28 reviews

A modern living space is showcased, featuring a comfortable sectional sofa and a large ottoman. The open kitchen, equipped with pendant lighting and bar seating, is visible in the background. Natural light floods the room through the windows, enhancing the airy atmosphere.

Townhouse in Windsor

Executive Home Rental

4.95 out of 5 average rating, 38 reviews

A comfortable living area features a navy blue sofa positioned near a glass coffee table. A television is displayed on an elegant metal stand. Bright natural light filters through sheer curtains, illuminating the soft gray carpeting.

Apartment in Walkerville

Come and relax at the BlueByU!

4.72 out of 5 average rating, 160 reviews

Apartment in Windsor

Affordable Urban Bachelor