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Apartment holiday rentals in Windsor

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Windsor

Guests agree: these apartments 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, 308 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.

Guest favourite
The living area features a dark geometric-patterned floor, complemented by exposed brick walls and wooden beams. A dartboard is mounted on a wall near a cozy seating arrangement, while a TV is placed above a fireplace. Decorative accents include warm-colored throw pillows.
Flat in Midtown
4.88 out of 5 average rating, 1,083 reviews

1890's Stone and Brick Garden Loft

Hello! Our home is an 1890 Victorian mansion that we purchased in 2016 and lovingly renovated over three years using a team of local craftspeople and myself. This space is a quirky 1 bedroom, 1 bath garden level loft with much of its original character preserved. Located in the heart of Midtown just one block from 15+ bars and restaurants, DMC, Shinola and way more. The space is designed with leisure stays in mind but also capable of accommodating business travelers comfortably. Parking included

Top guest favourite
A cozy living area features a black futon and a stylish armchair, both accompanied by table lamps on wooden side tables. A patterned rug lies on the hardwood floor, while light filters through a large window adorned with patterned curtains.
Flat in Hamtramck
4.93 out of 5 average rating, 194 reviews

Stylish 2 Bedroom w/ Dreamy Balcony

Our stylish and bright two bedroom flat with dreamy balcony is the perfect place to explore the hip underdog city of Detroit! The apartment is bright, stylish with all the modern amenities. Check out the rich culture, architecture and grittiness that is solely Detroit. BonVoyage :) We also have two other options: Charming Classic Apt in Arts & Culture Neighborhood https://www.airbnb.com/rooms/25067993?s=51 or Beautiful Apartment In Unique Hamtramck https://www.airbnb.com/rooms/6335682?s=51

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 LaSalle
4.87 out of 5 average rating, 220 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!

Top guest favourite
The living room features a comfortable sofa adorned with soft pillows, complemented by a contemporary coffee table. A cozy throw blanket rests on the seating. Natural light enters through a window, illuminating the artwork of a city skyline above the couch. An accent chair and lamps add to the inviting space.
Flat in Downtown Detroit
4.96 out of 5 average rating, 699 reviews

Stay downtown and walk everywhere!

Step out of your door and into the energy of downtown..This professionally maintained space offers the perfect home base for fans and theatre goers alike. Catch Tigers, Red Wings or Pistons this month , or secure your stay for the upcoming run of Hamilton. Coming up: Bruno Mars at Ford Field. After the final Whistle or the standing ovation, explore the culinary scene, featuring everything from world class restaurants to cozy hidden gem bars! Finally, retreat to a space designed for comfort.

Guest favourite
An inviting dining area features a long wooden table centered among charming accents. A variety of seating options, including stools and a wooden chair, complement exposed brick walls adorned with decorative wall art. Natural light softly illuminates the space, enhancing the rustic decor.
Flat in Corktown
4.9 out of 5 average rating, 509 reviews

Design-centric Corktown Apartment

A beautiful second-story apartment on Michigan Avenue with incredible views of the newly renovated train station, which is absolutely stunning all lit up out the big front windows. Situated on the same block as Alba, Sugar House, Ima, and Slows and across the street from Grandma Bob’s, this two-bedroom neighborhood flat provides an immersive, welcoming travel experience in the heart Corktown, Detroit's oldest neighborhood. Walk everywhere—15 minutes along Michigan Avenue will get you Downtown.

Superhost
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
4.91 out of 5 average rating, 113 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
The exterior of Little Caesars Arena is visible, featuring a well-lit roof and prominent signage. Bright beams of light radiate from the structure, illuminating the surrounding area. The skyline of the city is seen in the background, showcasing tall buildings against a twilight sky.
Flat in Brush Park
4.94 out of 5 average rating, 107 reviews

Downtown Detroit Getaway

With CITY VIEWS enjoy easy access to all VENUES and GAMES this Historically Vintage building is more than 90 years old. My apartment is located on the 6 floor with a gated elevator which sometimes does not work so if you can not walk to the sixth floor, this might not be for you. with only a block walk to little Caesars Areana and free parking. This is a diamond in the rough. Once in my Apt it’s cozy with all the comforts of home. I encourage week stays . Enjoy the Views!!

Guest favourite
A living area features exposed brick accents, with a cozy fireplace as a centerpiece. A light-colored sofa faces a low coffee table, enhanced by a colorful rug. A television is mounted on a unit displaying books and decorative items, while a rattan chair adds seating.
Flat in Brush Park
4.95 out of 5 average rating, 543 reviews

Little Paris of the Midwest - Walk to LCA, Ford

Nestled in historic Brush Park, known as Little Paris in the 19th century, this beautiful walk-up will immerse you in the city’s past while keeping you just steps from its future. Centrally located between Downtown, Midtown and Eastern Market, you'll be in the heart of the city with amazing bars, restaurants, cafes and venues just outside your door. The design-focused space is curated with goods made by local artisans and combines centuries old character with modern amenities.

Top guest favourite
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.
Flat in Walkerville
4.97 out of 5 average rating, 157 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

Guest favourite
A spacious living area features light wood flooring and ample natural light from large windows. Two comfortable chairs are positioned beside a modern coffee table. A gray sofa with colorful accent pillows sits in front of the TV, complemented by a decorative plant on the table.
Flat in Downtown Detroit
4.91 out of 5 average rating, 154 reviews

Downtown Large 1 BDRM, Walk Everywhere!

Located within a secure and recently renovated building walking distance to all the stadiums, theaters, dozens of restaurants and the Detroit Riverfront. It is a spacious one bedroom with a queen size bed and a pullout couch. Parking available on the street, or nearby lots. SPECIAL DISCOUNTS FOR CAST MEMBERS OF TOURING SHOWS- Inquire directly for more info We are 2 blocks from the Opera House and Fox Theater, and 2 miles from the Fisher Theater.

Guest favourite
A sectional sofa in a neutral tone occupies the living area, complemented by natural light filtering through bamboo blinds. A small throw blanket is draped over one section, and a soft area rug lies beneath, enhancing the comfort of the space.
Flat in Midtown
4.87 out of 5 average rating, 156 reviews

New Midtown listing, includes parking!

Tucked into the heart of the city, this spacious apartment provides a comfortable landing after a night out, or a day wandering through the nearby museums and cultural offerings of Detroit. Should you choose not to dine out at one of the award winning restaurants, or dive bars located within walking distance, this unit has a fully equipped kitchen. The off street parking is gated.

Popular amenities for Windsor apartment rentals

When is the best time to visit Windsor?

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Avg. price$112 SGD$107 SGD$113 SGD$120 SGD$132 SGD$124 SGD$122 SGD$127 SGD$120 SGD$121 SGD$116 SGD$113 SGD
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Quick stats about flat rentals in Windsor

  • Total holiday rentals

    Explore 540 holiday rentals in Windsor

  • Nightly prices starting at

    Windsor holiday rentals start at $25 SGD per night before taxes and fees

  • Verified guest reviews

    Over 36,420 verified reviews to help you choose

  • Family-friendly holiday rentals

    190 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 180 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    330 properties have a dedicated workspace

  • Wifi availability

    520 of Windsor holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool 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

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