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Our top choices for Windsor holiday homes
1. Affordable 1BHK close to Riverside, Casino, University & USA Border.
Affordable 1BHK close to Riverside, Casino, University & USA Border.Bridgeview
9.6 out of 10, Exceptional, (4 reviews)
"Great location, spacious."
Laurie
The price is £83
includes taxes & fees
16 Nov - 17 Nov
2. Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.
Luxury 2BR home with high ceilings with BBQ/ patio in beautiful South Windsor.South Windsor
10.0 out of 10, Exceptional, (22 reviews)
"Beautiful stay "
Mohamad C.
The price is £128
includes taxes & fees
13 Nov - 14 Nov
3. 🎰🚶♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9
🎰🚶♂️ Steps to Caesars 🌊 Riverfront 🍽️ Dining 💦 Hot Tub Add-On 🛏️ Sleeps 9Walkerville
8.8 out of 10, Excellent, (20 reviews)
"Great communication with host, clean, convenient parking and excellent location for events at Caesars!"
Valerie C.
The price is £178
includes taxes & fees
12 Nov - 13 Nov
4. 3 bdr upper, prime location
3 bdr upper, prime locationRemington Park
The price is £141
includes taxes & fees
16 Nov - 17 Nov
5. Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨
Hot Tub Retreat Near Downtown & Casino | Sleeps 8 | Cozy Luxury Stay for family✨City Centre
9.0 out of 10, Wonderful, (2 reviews)
"Great stay! Walking distance to all the things in the area."
Trent Y.
The price is £179
includes taxes & fees
25 Nov - 26 Nov
6. Cozy Modern Walkerville Basement Apartment
Cozy Modern Walkerville Basement ApartmentWalkerville
10.0 out of 10, Exceptional, (2 reviews)
"It was a nice clean place to spend the weekend."
Robin W.
The price is £82
includes taxes & fees
1 Dec - 2 Dec
7. Modern cozy home on the riverfront close to casino,downtown, Uof W and detroit
Modern cozy home on the riverfront close to casino,downtown, Uof W and detroitBridgeview
10.0 out of 10, Exceptional, (1 review)
"Nicely decorated with all the required items. Great location on the river with awesome views and great sunsets "
John P.
The price is £98
includes taxes & fees
16 Nov - 17 Nov
8. Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.
Elegant home 10mins drive to Detroit/Windsor border & 5 mins to Windsor airport.Devonshire
10.0 out of 10, Exceptional, (2 reviews)
"We had a great stay. The host was very responsive and addressed any issues quickly. The property was very clean, and the location was very convenient. Would definitely stay again."
Junwu
The price is £124
includes taxes & fees
12 Nov - 13 Nov
9. Unique 2-BDR Historic Warehouse Loft with Terrace and Fireplace ! ! !
Unique 2-BDR Historic Warehouse Loft with Terrace and Fireplace ! ! !Walkerville
10.0 out of 10, Exceptional, (9 reviews)
"Wonderful place to stay. Great location....perfect for two couples. Nice space indoors and outdoors."
Nicole C.
The price is £238
includes taxes & fees
12 Nov - 13 Nov
10. Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit border
Cozy home, 4 mins drive to Windsor airport & 10 mins drive to Detroit borderDevonshire
9.0 out of 10, Wonderful, (12 reviews)
"Home was very clean, good location close to major amenities, Devonshire mall, Costco. Easy access via key pad, ample parking. "
Tony
The price is £124
includes taxes & fees
12 Nov - 13 Nov
11. 7BR house 19 ppl DT Windsor Free Parking
7BR house 19 ppl DT Windsor Free ParkingCity Centre
4.0 out of 10, (1 review)
"The main floor refrigerator didn’t work and the roof leaked when it rained all over the master bed through the ceiling fan."
Mark D.
The price is £433
includes taxes & fees
15 Nov - 16 Nov
12. Fully Furnished 2 bedroom basement in Windsor
Fully Furnished 2 bedroom basement in WindsorWalkerville
4.8 out of 10, (3 reviews)
"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
The price is £105
includes taxes & fees
16 Nov - 17 Nov
13. Spacious 5-Bedroom Home in Central Windsor,ON – Near USA Border,
Spacious 5-Bedroom Home in Central Windsor,ON – Near USA Border,East Windsor
The price is £164
includes taxes & fees
16 Nov - 17 Nov
14. Premium Stay Near Windsor Employers & Hospital
Premium Stay Near Windsor Employers & HospitalFord City
9.0 out of 10, Wonderful, (11 reviews)
"Nice stay overall."
Adam Y.
The price is £160
includes taxes & fees
15 Nov - 16 Nov
15. The Windsor Mainstay
The Windsor MainstayBridgeview
10.0 out of 10, Exceptional, (1 review)
"Overall happy with the unitClose to activities we rented for water Park.Being close to train and moving of cars around at 2 am was disruptive."
rose h.
The price is £192
includes taxes & fees
15 Nov - 16 Nov
16. Modern Spacious 1 bedroom and a den home (Lower Unit)
Modern Spacious 1 bedroom and a den home (Lower Unit)Roseland
8.0 out of 10, Very good, (9 reviews)
"Very clean and everything that we thought it would be from the pictures"
Dannavan C.
The price is £164
includes taxes & fees
20 Nov - 21 Nov
17. Luxury getaway with pool and hot tub - family retreat
Luxury getaway with pool and hot tub - family retreatRoseland
7.2 out of 10, Good, (5 reviews)
"Clean and gorgeous backyard with heated pool and jacuzzi"
Mohammed M.
The price is £390
includes taxes & fees
12 Dec - 13 Dec
18. Luxury Home 10mins drive to Windsor/Detroit border, sleeps 11 guest
Luxury Home 10mins drive to Windsor/Detroit border, sleeps 11 guestDevonshire
10.0 out of 10, Exceptional, (2 reviews)
"Spacious, clean, and thoughtful amenities provided. Appreciated the closeness to the border as we were coming back from the US late in the evening."
Pauline
The price is £246
includes taxes & fees
12 Nov - 13 Nov
19. Executive One-Bedroom Upper Unit
Executive One-Bedroom Upper UnitWindsor
9.0 out of 10, Wonderful, (7 reviews)
"Property was as described. Very comfortable and in good condition. Excellent value."
Mary
The price is £99
includes taxes & fees
29 Nov - 30 Nov
20. 14th Coffee Co. Homestead Farmhouse
14th Coffee Co. Homestead FarmhouseEssex
9.6 out of 10, Exceptional, (9 reviews)
"House was excellent!!!
The only issue we experienced was the hot tub, it was so so strong with chlorine we couldn’t stay in it, ever our swim clothes got bleached."
Pete
The price is £160
includes taxes & fees
16 Nov - 17 Nov
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Windsor and related destinations
Directly across from Detroit, this riverside city offers stunning waterfront parks and the historic Walkerville district with local distilleries. Visitors can explore the colourful sculptures at Odette Sculpture Park or catch performances at the magnificent Capitol Theatre when they're not sampling poutine at local eateries.
Top reviews in Windsor
Stonecroft Inn
Stonecroft InnSouth Windsor
10/10 Excellent
Room was clean and newly refurbished. Beautiful.
HELEN
