Holiday houses in Windsor

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Top-rated holiday rentals in Windsor

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Guest favourite

Apartment in Windsor

4.94 out of 5 average rating, 185 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.

1 – 8 Oct

$962 AUD total

Guest favourite

Home in Windsor

4.89 out of 5 average rating, 179 reviews

Stunning Top Tier Modern Home Is Ready To Host You

Enjoy the luxurious feel of a modern home while you sit back and relax in Windsor’s hidden gem! Beautifully decorated and featuring a MASSIVE 1500 sq.ft living room with chic furniture, a pool table, state-of-the-art kitchen, and a high-ceiling 4 piece bathroom. Lots of nearby attractions! Spend a night out enjoying the views of the Detroit skyline after Game Night at Caesars! Head over to the University of Windsor to meet friends! Come home and nestle in the warmth of your clean & comfy bed!

13 – 20 Nov

$1,850 AUD total

Guest favourite

Guesthouse in Kingsville

4.96 out of 5 average rating, 213 reviews

Cozy Kingsville Country Guest House

Enjoy your stay in this cozy guest house on the main strip of the charming village of Cottam, within the town of Kingsville. This attached suite will be all for you. Separated from the main house with your own private entrance in the front and rear. Relax on the spacious deck overlooking the lush green mature treed backyard, roast marshmallows at the fire pit or take a nice nap on the hammock. Located a short drive to downtown Kingsville, beaches, wineries, restaurants, craft breweries and more!

10 – 17 Oct

$1,015 AUD total

Guest favourite

Guesthouse in Kingsville

4.98 out of 5 average rating, 593 reviews

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.

21 – 28 Mar

$1,368 AUD total

Guest favourite

Home in Windsor

4.94 out of 5 average rating, 103 reviews

Waterfront Home in Central City -KING BED 4 guests

Unwind in the newly renovated stylish WATERFRONT Home on Riverside Drive St of Windsor. Central City is full of Casino, restaurants, bars, shops, historic landmarks, and attractions. Adventure through Windsor and the region easily from this prime location. Once you are ready to relax, retreat to our comfy Home. ✔ 1.5 Rooms with King - 1 Twin size Beds ✔ Scenic Living room ✔ 2 Full washrooms ✔ Open Concept Living Area ✔ Office Space ✔ High-Speed Wi-Fi ✔ Central AC/HEAT ✔ Parking for 4 cars

15 – 22 Mar

$2,409 AUD total

Guest favourite

Cottage in Essex

4.92 out of 5 average rating, 319 reviews

Your Soulstice Studio

Become one with nature in this cozy cottage with an expansive view of the lake. Let yourself be absorbed by the sound of waves, birds and silence in the early morning hours. Sudden urge to do some yoga? No problem you have mats, blocks and bolsters to fulfill you ever stretching need! Your Soulstice is an up and coming yoga and massage studio that has been 2 years in the making. Now that it’s ready to open it’s doors, it needs a wee income to repay the “bank of mom” to show my appreciation! ♥️

20 – 27 June

$1,890 AUD total

Guest favourite

Guesthouse in Essex

4.99 out of 5 average rating, 293 reviews

Private Wine Route Getaway with Hot Tub

The heart behind The Vineyard Retreat is to help our guests relax, restore, and reconnect. Located on County Road 50 we're conveniently placed on the wine route between Kingsville, Colchester, and Harrow. Our guest house is steps away from Lake Erie and close by to wineries, breweries, restaurants, tours, fruit stands, national parks, conservation areas, beaches, orchards, golf courses, bike paths, and more. Read more about what our guest house has to offer in the detailed description below.

2 – 9 Sept

$1,779 AUD total

Guest favourite

Home in Kingsville

4.95 out of 5 average rating, 152 reviews

Heritage Lakehouse

Unwind at this modern lake house situated right on Lake Erie. The house was built with high ceilings and exposed raw steel accents throughout. Enjoy a stunning view of lake Erie from both bedrooms or through the 14 ft glass wall in the living room. The kitchen boasts all new appliances, quartz countertops and all of the cooking supplies needed. The house is located in between two public beaches and offers its own access into the lake. Wineries, Pelee Island, restaurants and golf courses.

22 – 29 Jan

$1,931 AUD total

Guest favourite

Guest suite in Windsor

4.97 out of 5 average rating, 158 reviews

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.

20 – 27 Apr

$1,551 AUD total

Superhost

Villa in Windsor

4.89 out of 5 average rating, 130 reviews

Cheerful 4-bedroom home by the river.

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.

23 – 30 Oct

$2,098 AUD total

Guest favourite

Guest suite in Windsor

4.92 out of 5 average rating, 309 reviews

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 late March to early November at 32°C (90°F). The hot tub is open year round.

24 June – 1 July

$1,344 AUD total

Guest favourite

Apartment in Windsor

4.95 out of 5 average rating, 55 reviews

The Boho Oasis: Studio Apartment

Welcome to The Boho Oasis!🪴 Our studio apartment is fully stocked with luxurious furniture, a fully-equipped kitchen, and features farmhouse, industrial, and bohemian themes. Enjoy high-speed wifi, and space for one car on the driveway with private back entrance. Located in a quiet neighborhood with easy access to local restaurants, grocery stores, parks, and the Detroit River just 10-minute walk away. Ideal for anyone seeking a trendy and comfortable stay!

28 Oct – 4 Nov

$1,054 AUD total

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Windsor holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near Windsor's top sights

Little Caesars Arena159 locals recommend

Comerica Park212 locals recommend

Ford Field164 locals recommend

Caesars Windsor102 locals recommend

Fox Theatre75 locals recommend

Hart Plaza66 locals recommend

Other great holiday rentals in Windsor

Guest favourite

Home in The Core

4.97 out of 5 average rating, 32 reviews

Boutique Suite on the River

7 – 14 May

$983 AUD total

Guest favourite

Apartment in The Core

4.94 out of 5 average rating, 62 reviews

Walkerville Loft (Main floor unit)

12 – 19 May

$1,033 AUD total

Guest favourite

Apartment in Windsor

5.0 out of 5 average rating, 20 reviews

Stylish luxury apartment

23 – 30 Mar

$945 AUD total

Superhost

Apartment in West Side

5.0 out of 5 average rating, 3 reviews

Cozy 2-bedrooms Apartment Unit for 4 Steps to UoW

3 – 10 Oct

$1,051 AUD total

Guest favourite

Home in Windsor

5.0 out of 5 average rating, 30 reviews

Perfect hideaway with a hot tub and a fireplace

30 Oct – 6 Nov

$1,816 AUD total

Guest favourite

Home in Windsor

4.92 out of 5 average rating, 84 reviews

"The Oasis" a Walkerville dream / 2 Bed - 1 Bath

30 May – 6 June

$1,200 AUD total

Guest favourite

Home in Windsor

5.0 out of 5 average rating, 24 reviews

The Spot - Luxury Living

2 – 9 Nov

$920 AUD total

Guest favourite

Apartment in The Core

4.9 out of 5 average rating, 20 reviews

Sun-filled bright 1BR by tunnel & casino

5 – 12 July

$1,524 AUD total

Show all

Quick stats about holiday rentals in Windsor

Total rentals	1.4K properties
Rentals with dedicated workspaces	830 properties have a dedicated workspace
Rentals with a pool	110 properties have a pool
Pet-friendly rentals	350 properties allow pets
Family-friendly rentals	570 properties are a good fit for families
Total number of reviews	65K reviews

Holiday houses in Windsor

Top-rated holiday rentals in Windsor

Apartment in Windsor

Home in Windsor

Guesthouse in Kingsville

Guesthouse in Kingsville

Home in Windsor

Cottage in Essex

Guesthouse in Essex

Home in Kingsville

Guest suite in Windsor

Villa in Windsor

Guest suite in Windsor

Apartment in Windsor

Holiday rentals for every style

Apartments

Houses

Hotels

Popular amenities for Windsor holiday rentals

Stay near Windsor's top sights

Other great holiday rentals in Windsor

Home in The Core

Apartment in The Core

Apartment in Windsor

Apartment in West Side

Home in Windsor

Home in Windsor

Home in Windsor

Apartment in The Core

Quick stats about holiday rentals in Windsor

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Destinations to explore