Holiday Rentals in Windsor

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Windsor

Our top choices for Windsor holiday rentals

Great Strip Location |WalktoLake|Wine Country|Brewing Company|A/C|Grill&Firepit

9.2 out of 10, Wonderful, (72)
"The place was very clean and well stocked. Communication was excellent check in was very easy with a code lock. Would definitely rent from him again. "
Great Strip Location |WalktoLake|Wine Country|Brewing Company|A/C|Grill&Firepit

Charming 1-bedroom cabin in Geneva

10.0 out of 10, Exceptional, (5)
"Friendly and generous hoste"
The price is €125
includes taxes & fees
4 Sept - 5 Sept
Charming 1-bedroom cabin in Geneva

Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries

9.4 out of 10, Exceptional, (252)
"This place was perfect! 16 ladies who needed to 'bug out of Dodge'; the location, space, fire pit, and bands hit thd spot! Will be back next year! And kudos to Matt the host, very accomodating."
Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries

Great Strip Location|Walk to Lake|Wine Country|A/C| Grill & Firepit|Family.

9.2 out of 10, Wonderful, (77)
"Nice location and close to town. The cottage was very clean. Really enjoyed the porch swing. The kitchen had everything we needed. We would stay again."
The price is €133
includes taxes & fees
11 Sept - 12 Sept
Great Strip Location|Walk to Lake|Wine Country|A/C| Grill & Firepit|Family.

Great Strip Location | Walk to Lake | Wine Country | A/C | Grill & Firepit

8.6 out of 10, Excellent, (66)
"It was a perfect little house for me an my 9 year old to stay in for the weekend of her dance competition!"
The price is €104
includes taxes & fees
28 Aug - 29 Aug
Great Strip Location | Walk to Lake | Wine Country | A/C | Grill & Firepit

LAKEFRONT LOFT-PERFECT COUPLES GETAWAY--rent 3 get 4th free 10/1-12/20-just ask!

10.0 out of 10, Exceptional, (348)
"Clean, nice updated shower and quiet but quick trip to many bars and restaurants."
The price is €141
includes taxes & fees
14 Sept - 15 Sept
LAKEFRONT LOFT-PERFECT COUPLES GETAWAY--rent 3 get 4th free 10/1-12/20-just ask!

Linny's GOTL Cottages "Lazy Days" Charming 2-bedroom bungalow with AC, GOTL.

10.0 out of 10, Exceptional, (14)
"It was very clean and cozy. Linney was great to deal with."
The price is €214
includes taxes & fees
19 Sept - 20 Sept
Linny's GOTL Cottages "Lazy Days" Charming 2-bedroom bungalow with AC, GOTL.

Lakefront condo --2BR/2Bath Sleeps 4 Private beach and lake front balcony

9.8 out of 10, Exceptional, (50)
"Awesome to watch sunset on the lake"
Lakefront condo --2BR/2Bath Sleeps 4 Private beach and lake front balcony

Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C

9.4 out of 10, Exceptional, (316)
"Do not miss out on this if your in the area it will not disappoint and is in the heart of GOTL. Feels like home,itll make you wish it was your home"
The price is €457
includes taxes & fees
14 Sept - 15 Sept
Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C

Pet Friendly | A/C | Wi-Fi & Cable | Grill |Walk to Lake| Firepit | Wine Country

9.6 out of 10, Exceptional, (196)
"It was a convenient location to the strip and the parks. "
The price is €191
includes taxes & fees
29 Aug - 30 Aug
Pet Friendly | A/C | Wi-Fi & Cable | Grill |Walk to Lake| Firepit | Wine Country

Cabin 1 The Sunrise Patio

9.0 out of 10, Wonderful, (4)
"Atmosphere cabin property and hosts where exceptional!Recommend contacting host before booking they are off grid (no electric, running water or sewer) "
The price is €136
includes taxes & fees
30 Aug - 31 Aug
Cabin 1 The Sunrise Patio

3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.

10.0 out of 10, Exceptional, (12)
"Wonderful cabin and owners. Easily a 5/5 with lots of things to do near by"
The price is €196
includes taxes & fees
8 Sept - 9 Sept
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.

Clean & Cozy Cottage - Lake Views + Private Hot Tub

9.8 out of 10, Exceptional, (21)
"Nice and helpful owners"
Clean & Cozy Cottage - Lake Views + Private Hot Tub

3Cottages on Strip, Lakefront, AC, WiFi, Fire pit, Deck over Lake, Pet Friendly

9.6 out of 10, Exceptional, (122)
"Great location and nice view. Perfect for our girls weekend. "
3Cottages on Strip, Lakefront, AC, WiFi, Fire pit, Deck over Lake, Pet Friendly

LAKE ERIE-SISTIBLE CONDO DIRECT WALK OUT to BEAUTIFUL LAKE ERIE

10.0 out of 10, Exceptional, (197)
"We had a wonderful stay on Lake Erie in this comfy and clean home. "
LAKE ERIE-SISTIBLE CONDO DIRECT WALK OUT to BEAUTIFUL LAKE ERIE

Modern 2B Family Home Near Wine Country- 6m Walk to Lake +Pet Friendly

9.8 out of 10, Exceptional, (71)
"Came in for a weekend stay had a good time"
The price is €168
includes taxes & fees
3 Sept - 4 Sept
Modern 2B Family Home Near Wine Country- 6m Walk to Lake +Pet Friendly

Beautiful newly remodeled cottage - Walk to strip, close to spire

10.0 out of 10, Exceptional, (95)
"Our stay couldn’t have been better. The place was amazing. The host was awesome and everything we needed was there! very clean comfortable and perfect for our weekend getaway."
The price is €240
includes taxes & fees
8 Sept - 9 Sept
Beautiful newly remodeled cottage - Walk to strip, close to spire

Main Strip Location | Pet Friendly | Wi-Fi & Cable | A/C | Steps from Winery

9.6 out of 10, Exceptional, (246)
"Great location and clean. The stay was perfect."
The price is €147
includes taxes & fees
1 Sept - 2 Sept
Main Strip Location | Pet Friendly | Wi-Fi & Cable | A/C | Steps from Winery

Great Strip Location | Walk to Lake| Wine Country | A/C | Grill & Firepit

9.0 out of 10, Wonderful, (97)
"Cute little cottage, very comfortable. Owner is very accommodating and returns text messages promptly. The BBQ grill and porch swing made us feel at home. Would definitely stay again. "
The price is €120
includes taxes & fees
7 Sept - 8 Sept
Great Strip Location | Walk to Lake| Wine Country | A/C | Grill & Firepit

Center Strip Location|Pet Friendly|Wi-Fi|A/C|Steps from Winery & Golf Course

9.4 out of 10, Exceptional, (214)
"It was located in a nice area! Firepit was an added bonus! Will stay again if ever in the area!"
Center Strip Location|Pet Friendly|Wi-Fi|A/C|Steps from Winery & Golf Course
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Windsor Hotel Reviews

Find out more about Windsor

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, apart-hotels, 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 €104 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 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?

Linny's GOTL Cottages "Lazy Days" Charming 2-bedroom bungalow with AC, GOTL.: This holiday home rental outside of Windsor is located on a lake, and offers a BBQ, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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.