Windsor Holiday Rentals from NZ$183: Search Short-Term Rentals

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Our top choices for Windsor holiday rentals

A modern living room with a grey sofa, a round coffee table, and a dining area with a table and chairs.

1. Windsor Manor

City Centre

Jacob

includes taxes & fees

18 Nov - 19 Nov

A living room with a glass table, a potted plant, a painting, a TV, and a window with curtains.

2. Affordable 1BHK close to Riverside, Casino, University & USA Border.

Bridgeview

Laurie

includes taxes & fees

2 Dec - 3 Dec

A modern living room with a blue sofa, grey armchairs, and a glass coffee table. There are framed pictures on the wall and a window with curtains.

3. Stylish 2bd DT Laundry and Parking

City Centre

A hallway with a marble floor, a bed in the background, and a wall with circular patterns.

4. Clean and spacious 3BR DT Windsor Laundry and parking

City Centre

A modern living room with a fireplace, a sofa, a coffee table, and a dining area.

5. Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel

City Centre

Stacy A.

includes taxes & fees

17 Nov - 18 Nov

A modern living room with a grey sofa, a white coffee table, and a flat-screen TV on a wooden stand.

6. Spacious Two Bedroom Suite Perfect For Longer Stays Sleeps 4

Walkerville

Mary M.

includes taxes & fees

17 Nov - 18 Nov

A modern kitchen with a large island, stainless steel sink, and white cabinetry.

7. Cozy Modern Walkerville Basement Apartment

Walkerville

Robin W.

includes taxes & fees

26 Nov - 27 Nov

A modern living room with a glass table and white chairs, a sofa with cushions, a brick accent wall, and artwork.

8. Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit

Bridgeview

John P.

includes taxes & fees

14 Dec - 15 Dec

A kitchen with a stainless steel refrigerator, a double sink, and a backsplash of gray tiles.

9. Windsor 1BR + Office | Business & Midterm Stays

Walkerville

harchetan

includes taxes & fees

16 Nov - 17 Nov

A kitchen with white cabinets, a black tiled backsplash, a window with a view of trees, and a stainless steel stove.

10. Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.

South Windsor

Mohamad C.

includes taxes & fees

15 Nov - 16 Nov

A single-story house with a front porch, a mailbox, and a number "627" on the wall.

11. 🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleep 10

Walkerville

Valerie C.

includes taxes & fees

15 Nov - 16 Nov

A couple in a hot tub with candles, wooden walls, and windows.

12. Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨

City Centre

Trent Y.

includes taxes & fees

14 Dec - 15 Dec

A narrow hallway with a refrigerator on the left, a door at the end, and a wall calendar on the right.

13. Cozy King Suite

Walkerville

includes taxes & fees

14 Nov - 15 Nov

A modern living room with a sofa, coffee table, and dining area.

14. 3 bdr upper, prime location

Remington Park

includes taxes & fees

15 Nov - 16 Nov

A modern living room with a glass table, grey sofas, and a staircase leading to a service area.

15. Windsor Perfect Stay

Remington Park

includes taxes & fees

15 Nov - 16 Nov

A modern living room with a flat-screen TV, a fireplace, a round mirror, and a sofa.

16. Beautiful gem with amazing view on the riverside

Bridgeview

Jenni T.

A hotel room with a large bed, two windows with curtains, a view of the city, and a small plant.

17. Walkerville 2BR Suite | Near Casino & Free Parking

Walkerville

Aidan

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with white cabinets, a microwave, stove, and two bar stools.

18. Walkerville 1BR Suite | Parking, Laundry & WiFi

Walkerville

A modern living room with a flat-screen TV mounted on the wall, a glass coffee table, and a grey sofa.

19. 6 Minutes to the Casino! Private Clean Suite Getaway | Work & Relax in Style

East Windsor

Kruz

includes taxes & fees

16 Nov - 17 Nov

20. Fully Furnished 2 bedroom basement in Windsor

Walkerville

"The home owner was incredibly nice and accommodating. They even picked us up from the train station nearby, and answered any msg quickly. I really appreciated that. Great neighborhood. The actual apartment wasn't quite what was advertised, the place wasn't as classy as the vrbo pictures. Also i thought vrbo was all about having a place to yourself? I was woken up a few times by footsteps upstairs where the owner lives. No laundry detergent, no bbq, 1 1/2 rolls of tp provided. Not worth the cost...

Kirk

includes taxes & fees

14 Nov - 15 Nov

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Top Windsor Hotel Reviews

Holiday Inn Express Windsor Waterfront by IHG

8/10 Good

"Could do more to accommodate a request. I booked two rooms under one name, when I when there we were totally separated and they were not accommodating to get us in the same floor. Was disappointed because the kids wanted to be together with the friends. Reception was not helpful at all. I was told it has to be under one name to accommodate my request. The breakfast was ok compared other holiday inns."

Super 8 by Wyndham Ambassador Bridge Windsor ON

10/10 Excellent

"Front desk staff were very helpful. Room was clean and well maintained. Parking was free and easy. Note - there is construction on Huron-Church in that area, so use the back street entrance. Breakfast was less than what comparable hotels offer. Cereal choices had no sugar free option. Only Frosted Flakes or Fruit Loops. More for kids."

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as NZ$183 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there holiday rentals in Windsor?

Yes, there are holiday rentals in Windsor close to Adventure Bay Family Water Park, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Windsor speak positively about the scenic riverfront and top-notch restaurants in this destination. While you're in the area, you can also enjoy the lively bars and live music.

What are some of the best holiday rentals that Windsor has to offer?

Premium Windsor Retreat |Perfect for Families, Groups & Long Stays+ Free Parking: This highly rated holiday home rental in Windsor offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden. Some other homes for rent in Windsor include 🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9 and Paradise Home - Your Home Away From Home.

How many holiday rentals will I find in Windsor?

With 111 Expedia holiday rentals, you're guaranteed to find just the right place for your Windsor stay.

What’s there to see and do in Windsor?

Family-friendly attractions include Adventure Bay Family Water Park and Olde Walkerville Neighborhood, whereas Windsor Riverfront and East Riverside Park are a couple of great spots to enjoy the outdoors. You’ll find favourite places to visit such as Ford Field and Little Caesars Arena in the wider area.

What’s a holiday rental in Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windsor. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive option for family trips.

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Check prices for these dates

Our top choices for Windsor holiday rentals

1. Windsor Manor

2. Affordable 1BHK close to Riverside, Casino, University & USA Border.

3. Stylish 2bd DT Laundry and Parking

4. Clean and spacious 3BR DT Windsor Laundry and parking

5. Bright and Cozy Nest in the City 1BR near River, Swim Park, Casino & Tunnel

6. Spacious Two Bedroom Suite Perfect For Longer Stays Sleeps 4

7. Cozy Modern Walkerville Basement Apartment

8. Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit

9. Windsor 1BR + Office | Business & Midterm Stays

10. Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.

11. 🎰🚶‍♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleep 10

12. Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨

13. Cozy King Suite

14. 3 bdr upper, prime location

15. Windsor Perfect Stay

16. Beautiful gem with amazing view on the riverside

17. Walkerville 2BR Suite | Near Casino & Free Parking

18. Walkerville 1BR Suite | Parking, Laundry & WiFi

19. 6 Minutes to the Casino! Private Clean Suite Getaway | Work & Relax in Style

20. Fully Furnished 2 bedroom basement in Windsor

Find holiday rentals that suit your style

Top Windsor Hotel Reviews

Holiday Inn Express Windsor Waterfront by IHG

Comfort Inn & Suites Ambassador Bridge

DoubleTree by Hilton Windsor Hotel & Suites

Four Points by Sheraton Windsor Downtown

Comfort Inn South Windsor

TownePlace Suites by Marriott Windsor

Super 8 by Wyndham Ambassador Bridge Windsor ON

Quality Inn & Suites Downtown Windsor

Super 8 by Wyndham Windsor/Dougall

Find out more about Windsor

Frequently asked questions

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