Holiday rentals in Windsor

4.95 out of 5 average rating, 267 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.

5 out of 5 average rating, 113 reviews

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.

4.9 out of 5 average rating, 155 reviews

Flat 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!

4.89 out of 5 average rating, 53 reviews

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, 108 reviews

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

4.8 out of 5 average rating, 182 reviews

Home in Riverside

Beautiful Oasis w/Heated Private Pool & Sunroom!

*HEATED POOL IS OPEN APRIL 1 - OCT 31* Welcome to Windsor’s largest and coziest stay! This gorgeous home blends modern design with comfort, featuring an inviting sunroom with soaring ceilings and natural light, perfect for morning coffee or quiet evenings. The chic decor creates a stylish, yet homey feel :) Unwind in a private backyard oasis with a 15x30, 8’ deep, in-ground oval pool with a brand NEW heater and BBQ lounge! Our backyard designed for a unique and relaxing family experience!

4.94 out of 5 average rating, 161 reviews

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.

4.98 out of 5 average rating, 214 reviews

Guest suite in Riverside

Glenn & Deb’s Place

1100 sq. ft guest suite attached to main residence but completely separate space on quiet residential street. Upper level with two bedrooms, washer/dryer and 1 bathroom with custom shower. Lower level has full kitchen, living room with gas fireplace, 42'' television and high speed internet. Independent heating and cooling. Owners are on site for quick response to all your needs. Close to WFCU, Caesars Windsor and all major arteries. We regret we are unable to accommodate pets.

4.89 out of 5 average rating, 186 reviews

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.

4.92 out of 5 average rating, 377 reviews

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.

4.75 out of 5 average rating, 114 reviews

Home in Windsor

stylish house in south windsor-2 bedrooms

Cozy 2BR Upper Unit – Prime Location Near Bridges & Top Retailers Welcome to your charming and fully renovated 2-bedroom upper unit in South Windsor, perfect for small groups or families. Thoughtfully designed for comfort, this inviting space is ideal for travelers seeking convenience and style. Whether you're here for business, leisure, or exploring Windsor and Detroit, this cozy retreat has everything you need. Book now for a convenient and comfortable stay!

4.91 out of 5 average rating, 185 reviews

Home in The Core

Downtown 2 Bed 1 Bath Unit w/ Free Parking

Welcome to our updated 2 bed 1 bath upper unit in downtown Windsor! With a fully equipped kitchen including stainless steel appliances & quartz countertops and a 65in TV with Netflix in the living room, this apartment has everything you need for a comfortable stay. Located near transit, shopping, and restaurants. This location is on a quiet block just minutes walk to the heart of downtown. Book now for a cozy and convenient home-away-from-home experience!

Holiday rentals for every style

Get the amount of space that is right for you

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Convenient locations with everyday essentials

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A space that's all yours, with room for everyone

Popular amenities for Windsor holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Windsor's top sights

Little Caesars Arena140 locals recommend

Ford Field124 locals recommend

Detroit Institute of Arts203 locals recommend

Eastern Market72 locals recommend

Campus Martius Park District133 locals recommend

Motown Museum140 locals recommend

Other great holiday rentals in Windsor

4.77 out of 5 average rating, 97 reviews

luxury 2-Bedroom Apartment In Downtown Windsor

DianeRating, 5 stars2 weeks ago

It was a pleasure staying in Windsor at the Airbnb. The place was pretty spacious for a basement. The rooms were a good size, which was a bonus. It was VERY clean and I highly recommend. They respond very fast and are very easy to communicate with. If you need a place to stay in Windsor, I would suggest this place, it was perfect for a family of 4.

5 out of 5 average rating, 30 reviews

Home in South Windsor

South Windsor Luxury Home - Private Gym/Sauna

CathrynRating, 5 stars1 week ago

Thank you for making us feel welcome! We thoroughly enjoyed our stay in your beautifully decorated space. The flowers, snacks, water and slippers were a personal touch. Lots of room to spread out and celebrate with family. The location was perfect for getting around Windsor easily. A peaceful oasis close by everywhere you wanted to go.

4.98 out of 5 average rating, 63 reviews

Guest house in The Core

Modern guest suite downtown

JaniceRating, 5 stars6 days ago

We have stayed at Heidi’s place twice- great location, great space, highly recommend!

5 out of 5 average rating, 93 reviews

Home in Windsor

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

ToshaRating, 5 stars1 week ago

In the beginning we had a small issue, Olivia was responsive and quickly resolved it. I was apprehensive about renting a town home, however I was pleasantly surprised. The home is elegant, spacious and well maintained. The neighborhood is really peaceful, and is in a great location. Olivia and her staff were professional and very friendly. We highly recommend and would stay there again for our future visits.

4.89 out of 5 average rating, 45 reviews

Flat in Windsor

Rare find by the Riverside

SheritaRating, 5 stars1 week ago

Very affordable very clean , balcony you can see ambassador bridge loved the home decor everything looked exactly as pictured would recommend and stay again !!!

4.94 out of 5 average rating, 31 reviews

Come and relax at the BlueByU!

WillRating, 5 stars2 weeks ago

Truly a wonderful experience staying at BlueByU, the cleanliness and hospitality made it feel like a home away from home. Very peaceful atmosphere as well as the neighbourhood. 10/10!

4.97 out of 5 average rating, 70 reviews

Home in South Windsor

Luxury 2BR home with high ceilings and BBQ w/patio

MichelleRating, 5 stars4 days ago

Wow! I am tempted to go back to Windsor just to stay at Ebrahim's Labelle Lodge! Everything, and I mean everything, was perfect and impeccably attended to. Ebrahim is an amazing host, going to the nth degree to ensure you are made to feel pampered. He makes all the difference while staying at his gem of a retreat. Thank you Ebrahim for going above and beyond!