Windsor Holiday Rentals

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Holiday Rentals in Windsor

Conveniently located 2 bedroom home only minutes from hiking and state park fun!
10.0 out of 10, Exceptional, (120)
"the host was very noce. check in was easy & the place was clean. nice & cozy. i would highly stay there again. "
United States
Duane C.
The price is AU$266
includes taxes & fees
21 Oct - 22 Oct
Conveniently located 2 bedroom home only minutes from hiking and state park fun!
No.1 Pinot Modern Cottage Heart of the Geneva Vineyards
2.0 star property
10.0 out of 10, Exceptional, (11)
"Everything was wonderful during our stay they had everything you needed and might need. The check in and out process was seamless and they are close to a ton of wineries."
United States
Laura C.
The price is AU$565
includes taxes & fees
27 Oct - 28 Oct
No.1 Pinot Modern Cottage Heart of the Geneva Vineyards
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
10.0 out of 10, Exceptional, (20)
"Wonderful cabin and owners. Easily a 5/5 with lots of things to do near by"
United States
Connor
The price is AU$316
includes taxes & fees
22 Oct - 23 Oct
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
Cabin 1 The Sunrise Patio
9.6 out of 10, Exceptional, (7)
"Atmosphere cabin property and hosts where exceptional!Recommend contacting host before booking they are off grid (no electric, running water or sewer) "
United States
Lora S.
The price is AU$240
includes taxes & fees
22 Oct - 23 Oct
Cabin 1 The Sunrise Patio
Ledgestone Farms-Rustic Western Getaway
8.6 out of 10, Excellent, (29)
"Great place to stay for a trip into nelson ledges. Clean and comfortable with WiFi access and a mini fridge. The property it's on is quite large and there are even some farm animals adding to the rustic ambiance. "
United States
Connor P.
The price is AU$266
includes taxes & fees
21 Oct - 22 Oct
Ledgestone Farms-Rustic Western Getaway
Lovely GOTL 2 Bedroom Cottage -Pet Friendly
10.0 out of 10, Exceptional, (38)
"The cottage is in a prime location. Close to the lake, many local shops, great restaurants. We had a great stay. Kelly is kind and responsive. The cottage was very clean and well stocked. I will stay at this cottage in the future. "
United States
Mandy
The price is AU$365
includes taxes & fees
21 Oct - 22 Oct
Lovely GOTL 2 Bedroom Cottage -Pet Friendly
Super Cute GOTL Two Bedroom Lake Erie Cottage
9.8 out of 10, Exceptional, (27)
"The property was wonderful and the host was fantastic! We will definitely stay here again in the future. "
United States
Angie B.
The price is AU$365
includes taxes & fees
21 Oct - 22 Oct
Super Cute GOTL Two Bedroom Lake Erie Cottage
1st Floor Beach Access 2-Bedroom Condo in Geneva U1
8.0 out of 10, Very good, (3)
"The property was in a great location. Nice an quiet, yet walkable to all attractions!"
United States
Vicky C.
The price is AU$344
includes taxes & fees
21 Oct - 22 Oct
1st Floor Beach Access 2-Bedroom Condo in Geneva U1
Cozy Shed-Teau in Geneva
8.0 out of 10, Very good, (2)
"Your place was beautiful. Unfortunately we did not get to spend the night as planned. Thank you."
United States
Lori S.
The price is AU$186
includes taxes & fees
21 Oct - 22 Oct
Cozy Shed-Teau in Geneva
Ledgestone Farms-Cozy Farm Apartment
9.4 out of 10, Exceptional, (50)
"Visiting family in the area- 3rd time we have stayed here, and clean, cozy, and convenient every time! "
United States
Alaina W.
The price is AU$266
includes taxes & fees
21 Oct - 22 Oct
Ledgestone Farms-Cozy Farm Apartment
Beautiful cabin situated on wooded land with nice yard clearing and small stream
9.8 out of 10, Exceptional, (10)
"The location was very peaceful and relaxing. We felt at home with nature and enjoyed our time very much!"
United States
Steven B.
The price is AU$255
includes taxes & fees
1 Nov - 2 Nov
Beautiful cabin situated on wooded land with nice yard clearing and small stream
Beautiful newly remodeled cottage - Walk to strip, close to spire
10.0 out of 10, Exceptional, (104)
"The poroperty was perfect. Quality renovation. Private. Just like home"
United States
Tina
The price is AU$333
includes taxes & fees
2 Nov - 3 Nov
Beautiful newly remodeled cottage - Walk to strip, close to spire
Little house on the farm
10.0 out of 10, Exceptional, (94)
"It is perfect. Jim the owner communicated very quickly with any questions I had. The house was extremely clean. We had a great stay and highly recommend this home. You won’t be disappointed. "
United States
Anthony
The price is AU$352
includes taxes & fees
21 Oct - 22 Oct
Little house on the farm
Keys cottage -walk to the strip,Private lot, 2bdr 3rd guestroom detached.Spire
10.0 out of 10, Exceptional, (103)
"Beautiful little cottage, tucked not too far from the strip. Neighbors were all very nice and friendly. 10/10 will come back! "
United States
Krysta F.
The price is AU$320
includes taxes & fees
3 Nov - 4 Nov
Keys cottage -walk to the strip,Private lot, 2bdr 3rd guestroom detached.Spire
3 Little Cottages - #1 Sundance Cottage
9.8 out of 10, Exceptional, (39)
"The cottage was cute and clean. It was nice to be such a short walk to the strip- yet it was very quiet so you can sleep. We had a wonderful time! "
United States
Linda C.
The price is AU$445
includes taxes & fees
1 Nov - 2 Nov
3 Little Cottages - #1 Sundance Cottage
LEMON DROP LAKE FRONT COTTAGE
10.0 out of 10, Exceptional, (13)
"Great little place on the lake. We lived our stay."
United States
robin c.
The price is AU$374
includes taxes & fees
26 Oct - 27 Oct
LEMON DROP LAKE FRONT COTTAGE
A great stay, close to Spire, GOTL, & Wineries....King Bed!
10.0 out of 10, Exceptional, (37)
"This property was perfect for our one night stay in Geneva. Very pleased with the cleanliness."
United States
Kathleen M.
The price is AU$280
includes taxes & fees
23 Oct - 24 Oct
A great stay, close to Spire, GOTL, & Wineries....King Bed!
Sleeps 8-Cozy 3-Bedroom Cottage, 2 Blocks from the Strip, 10 Minutes from Spire
10.0 out of 10, Exceptional, (17)
"The property was nice and great location. "
United States
Michelle S.
Sleeps 8-Cozy 3-Bedroom Cottage, 2 Blocks from the Strip, 10 Minutes from Spire
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
10.0 out of 10, Exceptional, (7)
"Loved this property. Was so clean and nice. "
United States
Allyson C.
The price is AU$307
includes taxes & fees
23 Oct - 24 Oct
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
Little oasis a short walk from GOTL strip
10.0 out of 10, Exceptional, (89)
"Enjoyed the stay"
United States
Mike C.
The price is AU$309
includes taxes & fees
26 Oct - 27 Oct
Little oasis a short walk from GOTL strip
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.
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Top Windsor Hotel Reviews

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 favourite 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 depend 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 AU$240 per night. Entering your travel dates in the search wizard might find you 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 close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay.

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

Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries: This holiday home rental outside of Windsor is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 10 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.

What can I see and do in Windsor?

While exploring the area, visit family-friendly sights like Pioneer Waterland & Dry Fun Park, or get outside and enjoy nature at Punderson Lake. Windsor Mills Covered Bridge and Riverdale Road Covered Bridge are a couple of places you'll find in the wider area.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family trips.