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Holiday rentals in Windsor

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Top-rated holiday rentals in Windsor

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
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.
Flat in Walkerville
4.95 out of 5 average rating, 303 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.

Superhost
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.
Flat in Downtown Windsor
4.69 out of 5 average rating, 234 reviews

AKSUM- Location! Lovely Studio, Ensuite Shower, AC

We are in Windsor, Canada Enjoy a stylish experience at our centrally located unit of modern elegance and minimalism. Close to many of Windsor's key destinations Aksum is an independent unit with ensuite bathroom (shower) Walk to appointments at City Hall (2min), to the casino or Walkerville or scenic riverfront (5min), Downtown St. Clair and to restaurants You'll be at the Detroit tunnel in 1 min. Bus stop is just outside for easy access to train station and Univ of Windsor No visitors allowed.

Top guest favourite
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
4.98 out of 5 average rating, 131 reviews

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.

Guest favourite
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.
Flat in Windsor
4.87 out of 5 average rating, 205 reviews

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!

Superhost
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
4.83 out of 5 average rating, 117 reviews

Private 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!

Top guest favourite
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
4.97 out of 5 average rating, 145 reviews

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

Top guest favourite
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
4.94 out of 5 average rating, 122 reviews

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.

Guest favourite
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.
Flat in Walkerville
4.93 out of 5 average rating, 111 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.

Guest favourite
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
4.94 out of 5 average rating, 192 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.

Guest favourite
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
4.93 out of 5 average rating, 28 reviews

Serene Green 2BR Haven in Little Italy

Welcome to this luxurious 2-bedroom home featuring European designer furniture — family-friendly and work-from-home ready. Enjoy 5-star hotel beds, a renovated kitchen with stainless steel appliances, free laundry, Wifi, standing desks, a plush velvet sofa with a 50" TV, and convenient on-street free parking. Centrally located in Windsor, just a 5–10 min walk to Italian dining and shops, with easy access to Windsor downtown, Detroit border, Highway 401, and Windsor Regional Hospital.

Top guest favourite
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
4.99 out of 5 average rating, 122 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!

Top guest favourite
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.
Flat in Walkerville
4.95 out of 5 average rating, 40 reviews

Come and relax at the BlueByU!

Beautifully decorated, blue-themed upper one-bedroom Executive Apartment. Ideal for business travel or romantic getaways. Conveniently located in the heart of Walkersville, the bright unit has a queen-sized bed, a beautiful kitchen and bathroom, a spacious dining area, a stunning living room, and a small office. We are located only 15 minutes from downtown Detroit via the tunnel, 15 minutes from Windsor’s airport, and 5 minutes from the Via train station.

Popular amenities for Windsor holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Windsor's top sights

Little Caesars Arena

319 locals recommend

Ford Field

307 locals recommend

Hart Plaza

108 locals recommend

Detroit Institute of Arts

768 locals recommend

Belle Isle

188 locals recommend

Eastern Market

382 locals recommend

Other great holiday rentals in Windsor

Guest favourite
A modern kitchen features sleek white cabinets and quartz countertops. Stainless steel appliances are neatly arranged, with barstools positioned at a large island. Natural light streams through multiple windows, highlighting the clean lines and minimalist design of the space.
Private room in South Windsor
4.97 out of 5 average rating, 67 reviews

Near 401, restaurants, plazas, Walmart, US border

Flat in Windsor
4.67 out of 5 average rating, 39 reviews

Cozy, Clean & Bright 2Bd - Great for long stays

Home in Windsor
5 out of 5 average rating, 4 reviews

A stunning view, right on the Riverside.

Guest favourite
A cozy living area features a comfortable brown sofa alongside two yellow chairs. A rounded coffee table sits in front of the sofa, and natural light fills the space through large windows, which overlook a garden area. Neutral tones create a welcoming atmosphere.
Home in Walkerville
4.83 out of 5 average rating, 35 reviews

The Hipster House

Guest favourite
Private room in Windsor
4.82 out of 5 average rating, 227 reviews

Maryjoe's

Top guest favourite
The exterior of a two-story brick house is showcased, featuring a stately entrance with double doors and a wide staircase. Well-maintained shrubs and small trees frame the front, while a paved driveway leads up to the entrance. Neutral-colored walls and dark accents complement the inviting facade.
Private room in South Windsor
4.92 out of 5 average rating, 61 reviews

Quiet and comfortable room #2

Guest favourite
A comfortable bedroom features a soft-toned walls and a spacious bed with a checked duvet. A lamp beside the bed provides warm light, while a writing desk and chair add functionality. A decorative chair is placed in the corner, and a towel lies neatly on a bench at the foot of the bed.
Private room in Windsor
4.92 out of 5 average rating, 37 reviews

Travelhome in the basement 1

Guest favourite
A cozy room features a metal bed with a floral-patterned bedspread. Natural light enters through a window dressed with floral curtains. A small table with a glass top is paired with a chair, while a white dresser is positioned nearby, adorned with neatly folded items.
Private room in Downtown Windsor
4.86 out of 5 average rating, 50 reviews

#2 Comfy Room in Downtown near UoW/Tunnel

When is the best time to visit Windsor?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price₹7,527₹7,619₹7,986₹7,986₹8,629₹8,170₹7,986₹8,537₹7,894₹8,629₹8,261₹7,986
Avg. temp-3°C-2°C3°C9°C16°C21°C23°C22°C18°C12°C5°C0°C

Frequently Asked Questions

  • What are the best places to stay in Windsor?

    Windsor has a mix of centrally located neighborhoods near the waterfront, Walkerville for its historic vibe, and Riverside for quieter stays close to parks. Consider areas around downtown if you enjoy easy access to restaurants and cultural sites.

  • What are the best things to do in Windsor with kids?

    Windsor has hands-on exhibits at the Chimczuk Museum, outdoor artwork along the Windsor Sculpture Park, and green spaces for picnics or play along the riverfront. Families also spend time exploring local playgrounds and community events throughout the year.

  • What are some of the best things to do in Windsor?

    Explore the Windsor Sculpture Park, stroll the scenic waterfront, and experience the art galleries around downtown. The city also has historical sites rooted in diverse communities and vibrant food markets.

  • How is the weather in Windsor?

    Windsor has cold winters with temperatures from 19–37°F (-7–3°C), and warm summers ranging 63–84°F (17–29°C). Spring and autumn bring milder weather; packing a mix of layers and a rain jacket is often suggested.

  • When is the best time to visit Windsor?

    Late spring through early autumn is often recommended for comfortable temperatures and outdoor festivals. Visitors frequently enjoy riverfront activities and gardens during these months.

  • What are the best places to visit in Windsor?

    Many explore the Windsor Sculpture Park, Jackson Park's seasonal gardens, and the Art Gallery of Windsor. History enthusiasts may appreciate heritage sites in Walkerville and the local museum.

  • What are some hiking trails in Windsor?

    Windsor has nature trails in Ojibway Prairie Complex, scenic riverfront paths, and wooded routes through Malden Park. These are frequently suggested for walking, birdwatching, and enjoying local plants.

  • What are some family activities we can do in Windsor?

    Families in Windsor explore interactive displays at the Chimczuk Museum, stroll through the Windsor Sculpture Park, and gather at riverside parks for outdoor fun. Seasonal community events and local markets also welcome visitors of all ages.

  • What are some of the best day trip ideas from Windsor?

    Consider exploring Point Pelee National Park for nature walks, venturing to local wineries for tastings, or visiting neighboring towns with distinct cultural and culinary experiences. Outdoor enthusiasts also enjoy regional conservation areas and sandy beaches around the region.

  • Are there any pet friendly accommodations available in Windsor?

    Many Windsor vacation rentals and stays are pet-friendly, especially in neighborhoods like Riverside, Walkerville, and near green spaces. Check specific listings for details, as rules may vary by property.

  • What are some local tips for visiting Windsor?

    Locals suggest strolling the waterfront trail at sunset, exploring historic Walkerville for its cafes and shops, and sampling locally made pastries. Packing comfortable walking shoes is helpful, as many highlights are best on foot.

  • What is Windsor known for?

    Windsor is known for its multicultural heritage, automotive history, and vibrant riverfront stretching along the Detroit River. The city has a strong connection to Canadian whisky traditions and is often recognized for its public art installations.

  • What are the best hidden gems to explore in Windsor?

    Seek out street art and indie shops in Ford City, local bakeries with longstanding recipes, and small heritage museums tucked into neighborhood corners. Ojibway Prairie Complex is often recommended for those interested in native plants and quiet walking trails.

  • What are the best foods to try in Windsor?

    Windsor is frequently suggested for its locally made pizza known for signature shredded pepperoni, Lebanese grilled dishes, and classic Canadian butter tarts. Polish, Italian, and Middle Eastern bakeries also feature beloved pastries and breads.

  • What should I bring for a trip to Windsor?

    Pack layers to suit changing seasons, a rain jacket, and comfortable shoes for exploring parks and city strolls. Bringing a reusable water bottle and sun protection is often handy if you plan to spend time outdoors.

  • What is the nightlife in Windsor like?

    Windsor's nightlife has a variety of laid-back pubs, music venues, and cocktail bars, especially around downtown and Ouellette Avenue. Some neighborhoods also have lounges with live bands and dance floors for a mix of experiences.

  • What are the most popular events or festivals in Windsor?

    Windsor hosts a popular summer waterfront fireworks display, the Windsor International Film Festival in autumn, and seasonal multicultural festivals celebrating local communities. Outdoor concerts and food events are frequently suggested during warmer months.

  • Are there family friendly vacation rentals in Windsor?

    Many Windsor vacation rentals are suited to families, with larger spaces available near parks or in Walkerville and Riverside neighborhoods. Check for listings with amenities like kitchens and extra bedrooms for added comfort.

Quick stats about holiday rentals in Windsor

  • Total holiday rentals

    Explore 1,660 holiday rentals in Windsor

  • Nightly prices starting at

    Windsor holiday rentals start at ₹918 per night before taxes and fees

  • Verified guest reviews

    Over 88,400 verified reviews to help you choose

  • Family-friendly holiday rentals

    690 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 420 rentals that welcome pets

  • Holiday rentals with a pool

    50 properties feature pools

  • Rentals with dedicated workspaces

    990 properties have a dedicated workspace

  • Wifi availability

    1,610 of Windsor holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Windsor rentals

  • 4.7 Average rating

    Windsor stays receive an average rating of 4.7 out of 5 from guests

  • Nearby attractions

    Windsor’s top spots include Little Caesars Arena, Comerica Park and Ford Field

Destinations to explore

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