Holiday Rentals in Windsor

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Holiday Rentals in Windsor

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

8.8 out of 10, Excellent, (101)
"Fantastic, loved our cabin! "
The price is €101
includes taxes & fees
16 Oct - 17 Oct
Great Strip Location | Walk to Lake| Wine Country | A/C | Grill & Firepit

Great Strip Location|WalktoLake|Wine Country|AC|Grill&Firepit|FamilyFriendly

9.4 out of 10, Exceptional, (101)
"What a great 2 night stay we had at the Eagle Cliff Inn suite 6. Matt, the host was great at communicating. Suite was lovely, very large, clean,with that Geneva feel. Well stocked with plenty of towels and everything you need in the kitchen! Also there were outside firepits and Matt kept plenty of firewood. Highly recommend!"
The price is €135
includes taxes & fees
15 Oct - 16 Oct
Great Strip Location|WalktoLake|Wine Country|AC|Grill&Firepit|FamilyFriendly

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

9.4 out of 10, Exceptional, (257)
"We had a great time staying here, with all my grown siblings - thank you!"
Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries

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

9.4 out of 10, Exceptional, (218)
"It was located in a nice area! Firepit was an added bonus! Will stay again if ever in the area!"
The price is €131
includes taxes & fees
12 Oct - 13 Oct
Center Strip Location|Pet Friendly|Wi-Fi|A/C|Steps from Winery & Golf Course

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

9.2 out of 10, Wonderful, (77)
"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

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

9.6 out of 10, Exceptional, (253)
"Great location and clean. The stay was perfect."
Main Strip Location | Pet Friendly | Wi-Fi & Cable | A/C | Steps from Winery

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

9.6 out of 10, Exceptional, (202)
"Wonderful host and stay!"
Pet Friendly | A/C | Wi-Fi & Cable | Grill |Walk to Lake| Firepit | Wine Country

Great Strip Location | Lake View | Pet Friendly | A/C | Sauna| Wine Country|WiFi

9.8 out of 10, Exceptional, (203)
"Great location and plenty of space. Everything was clean and operational. Host was great communicator. Would consider staying here again!"
Great Strip Location | Lake View | Pet Friendly | A/C | Sauna| Wine Country|WiFi

Cabin 1 The Sunrise Patio

9.4 out of 10, Exceptional, (6)
"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
13 Oct - 14 Oct
Cabin 1 The Sunrise Patio

Lakefront Home Water Front Pet Friendly Steps from Winery Wi-Fi & Cable

9.4 out of 10, Exceptional, (324)
"Perfect for a family!"
Lakefront Home Water Front Pet Friendly Steps from Winery Wi-Fi & Cable

Strip Location | Pet Friendly | A/C | Wi-Fi & Cable | Fire Pit | Wine Country

9.6 out of 10, Exceptional, (229)
"Very clean and neat , perfect for 6 people "
Strip Location | Pet Friendly | A/C | Wi-Fi & Cable | Fire Pit | Wine Country

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

9.6 out of 10, Exceptional, (126)
"Great location. 11 of us stayed in the 3 cottages, with dogs and all went well! Highly recommend!"
3Cottages on Strip, Lakefront, AC, WiFi, Fire pit, Deck over Lake, Pet Friendly

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

9.2 out of 10, Wonderful, (84)
"Had everything we needed and very close location to walk to everything. "
Great Strip Location|Walk to Lake|Wine Country|A/C| Grill & Firepit|Family.

East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly

9.4 out of 10, Exceptional, (91)
"It was a perfect place for our group of 6! Not a bad walk to the shops/bars, unless it is raining (speaking from experience lol). Very clean and easy to access. The area around it was nice and quiet. Would definitely stay again!"
East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly

Charming 1-bedroom cabin in Geneva

9.8 out of 10, Exceptional, (7)
"Friendly and generous hoste"
The price is €125
includes taxes & fees
13 Oct - 14 Oct
Charming 1-bedroom cabin in Geneva

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

9.8 out of 10, Exceptional, (77)
"Came in for a weekend stay had a good time"
Modern 2B Family Home Near Wine Country- 6m Walk to Lake +Pet Friendly

DewDrop Cottage: Walk to the strip! 2 bed 1 bath, sleeps 5

10.0 out of 10, Exceptional, (202)
"We looked to get away from cleveland for a few days. Wanted to enjoy a different area within the state. Great location! Cute little house, very clean. Everything is very close either walking or driving."
The price is €349
includes taxes & fees
13 Oct - 14 Oct
DewDrop Cottage: Walk to the strip! 2 bed 1 bath, sleeps 5

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. "
The price is €269
includes taxes & fees
12 Oct - 13 Oct
Lovely GOTL 2 Bedroom Cottage -Pet Friendly

Quaint cottage a short walk from the GTOL strip!

9.8 out of 10, Exceptional, (55)
"This was the perfect cottage!!! Absolutely perfect"
The price is €182
includes taxes & fees
11 Nov - 12 Nov
Quaint cottage a short walk from the GTOL strip!

Center of Strip |Pet Friendly|A/C|Wi-fi & Cable|Stately Home|Steps from Winery

9.4 out of 10, Exceptional, (244)
"We take our family every year for a staycation close to Erie. This was a great place to stay. Everyone enjoyed the location!!"
Center of Strip |Pet Friendly|A/C|Wi-fi & Cable|Stately Home|Steps from Winery
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, 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 €101 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?

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.