Holiday rentals in Windsor

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Top-rated holiday rentals in Windsor

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Guest favourite

Rental unit in The Core

4.94 out of 5 average rating, 223 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

Home in The Core

4.89 out of 5 average rating, 140 reviews

Stylish South Walkerville Home w Hot-Tub & Firepit

Welcome to this Stylish Home Away From Home! 1 King Bed & Ensuite on the 2nd Floor. 2 Bedrooms (2 Queens+1 Top Twin Bunk) & Full Bath on the Main Floor + 1 Queen Bed in the Basement. Bring Together 1 or 2 Families of up to 9 people for your next visit to Windsor ON. Located in the Very Desirable Neighbourhood of South Walkerville. Enjoy an evening Soak in the Hot-Tub & a Relaxing Experience by the Gas Fire-Pit in the Backyard. Please note the basement has a kitchenette not currently functional.

Superhost

Home in The Core

4.85 out of 5 average rating, 219 reviews

Year Round Hot Tub, Walkerville Charm Home

This stunning 4 bedroom, 6 bed home is dressed to impress! We have spared no detail to ensure your comfort, including: * a private 6 person hot tub; *4 Casper queen beds; * 2 Casper full beds; * a Weber gas BBQ; * lightning fast WIFI connection; * a 50-inch smart Samsung TV in the living room; * a 55-inch smart Samsung TV on the upper floor; * a large formal dining room; * an open concept dining/living/sitting space which can comfortably seat 14 people; * a kids' korner for playtime; * and+++

Guest favourite

Guest house in Kingsville

4.98 out of 5 average rating, 639 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.

Guest favourite

Home in Riverside

4.89 out of 5 average rating, 118 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

Guest favourite

Cottage in Essex

4.93 out of 5 average rating, 361 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! ♥️

Guest favourite

Guest house in Essex

4.99 out of 5 average rating, 326 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.

Guest favourite

Home in Kingsville

4.95 out of 5 average rating, 191 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.

Guest favourite

Home in The Core

4.94 out of 5 average rating, 125 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

Guest suite in Riverside

4.98 out of 5 average rating, 192 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.

Superhost

Villa in Windsor

4.9 out of 5 average rating, 156 reviews

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.

Guest favourite

Guest suite in Windsor

4.92 out of 5 average rating, 354 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.