Windsor Holiday Rentals

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Holiday Rentals in Windsor

Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C
9.4 out of 10, Exceptional, (271)
"Great time! Perfect location"
The price is NZ$1,099
per night
20 Jun - 21 Jun
Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C
3Cottages on Strip, Lakefront, AC, WiFi, Fire pit, Deck over Lake, Pet Friendly
9.8 out of 10, Exceptional, (91)
"Very nice places with a great price"
3Cottages on Strip, Lakefront, AC, WiFi, Fire pit, Deck over Lake, Pet Friendly
East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly
9.6 out of 10, Exceptional, (51)
"My mom and I came from TN for a wedding in Madison. This place was a great place and just about 20 minutes from the wedding and family. There is a park across the road with great views of the lake. The house is clean and stocked with everything needed for a get away. The only downfalls were the stair case is steep so it might be difficult for some and the parking has signs but some are missing so parking might be tight during the busy season. Overall, great place and I would stay there again."
East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly
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Great Strip Location | Walk to Lake| Wine Country | A/C | Grill & Firepit
9.2 out of 10, Wonderful, (54)
"Nice little house, but it was a little smaller than what I expected. We had just enough space."
Great Strip Location | Walk to Lake| Wine Country | A/C | Grill & Firepit
Great Strip Location|Walk to Lake|Wine Country|A/C| Grill & Firepit|Family.
9.6 out of 10, Exceptional, (47)
"Perfect for a couple wanting to get away and walk to everything. We also love visiting the wineries so the cottage was the ideal location for all our destinations. We would stay here again!"
The price is NZ$265
per night
31 May - 1 Jun
Great Strip Location|Walk to Lake|Wine Country|A/C| Grill & Firepit|Family.
Endless Summer - Sleeps 6 Condo
10.0 out of 10, Exceptional, (60)
"The units location is the perfect place to enjoy GOTL… not in the middle of the strip, yet very close. It is one of the few rentals that provides beach access. The unit is beautiful, spacious and clean. We had everything needed to enjoy a wonderful vacation!"
Endless Summer - Sleeps 6 Condo
Main Strip Location | Pet Friendly | Wi-Fi & Cable | A/C | Steps from Winery
9.6 out of 10, Exceptional, (203)
"Came up for our anniversary and had a nice stay. Several restaurants close within walking distance"
The price is NZ$329
per night
19 Jun - 20 Jun
Main Strip Location | Pet Friendly | Wi-Fi & Cable | A/C | Steps from Winery
GOTL Coastal Cottage- Sunset Vacation Rentals
9.2 out of 10, Wonderful, (66)
"We stayed two nights while attending a wedding. The location worked great for GOTL, with a view of Lake Erie from the living room. The house was clean and neat inside, though musty. The exterior decks were dangerous with a hole through the floor in one and a bottom step missing from the other."
GOTL Coastal Cottage- Sunset Vacation Rentals
Family Fun And Beautiful Views On Lake Erie. Perfect Luxury Condo/Indoor Pool
10.0 out of 10, Exceptional, (280)
"We booked this location on a whim for my husband’s birthday & it didn’t disappoint. The view of the lake was breathtaking! We loved having private access to the little beach and the condo was very quiet which made for a relaxing trip! We can’t wait to book again next year!"
Family Fun And Beautiful Views On Lake Erie. Perfect Luxury Condo/Indoor Pool
Strip Location | Pet Friendly | A/C | Wi-Fi & Cable | Fire Pit | Wine Country
9.6 out of 10, Exceptional, (185)
"This house is exactly what we wanted for our weekend away!! Great location! Will definitely stay again!"
Strip Location | Pet Friendly | A/C | Wi-Fi & Cable | Fire Pit | Wine Country
Great Strip Location |WalktoLake|Wine Country|Brewing Company|A/C|Grill&Firepit
9.2 out of 10, Wonderful, (48)
"This location was great! Lots of parking. The location was near the end of the strip, but still close enough that you were able to walk to everything. Right next to East End, so you got to enjoy the live music while hanging out by the fire pits. The place was very clean. While small, the pictures don’t do the space justice and we found it to be rather roomy. The only complaint is the heater. We made sure it was unplugged and turned off, but every three hours or so it kept heating up, which made...
Great Strip Location |WalktoLake|Wine Country|Brewing Company|A/C|Grill&Firepit
DewDrop Cottage: Walk to the strip! 2 bed 1 bath, sleeps 5
10.0 out of 10, Exceptional, (169)
"The place was great. Would certainly stay here again"
The price is NZ$534
per night
4 Jun - 5 Jun
DewDrop Cottage: Walk to the strip! 2 bed 1 bath, sleeps 5
Great Strip Location | Walk to Lake|Wine Country|A/C|Fireplace|Family Friendly
9.6 out of 10, Exceptional, (67)
"Everything was cool it was nice good area right on the strip i enjoy my stay it was awesome everything was there u need"
Great Strip Location | Walk to Lake|Wine Country|A/C|Fireplace|Family Friendly
beautiful newly remodeled cottage - Walk to strip close to spire
10.0 out of 10, Exceptional, (36)
"Well equipped, comfy home"
The price is NZ$469
per night
25 Jun - 26 Jun
beautiful newly remodeled cottage - Walk to strip close to spire
Center Strip Location|Pet Friendly|Wi-Fi|A/C|Steps from Winery & Golf Course
9.4 out of 10, Exceptional, (168)
"This was the second time staying at this location. Great walking distance to strip and plenty of parking. Plenty of space for my fiancé and our dog. Would highly recommend."
Center Strip Location|Pet Friendly|Wi-Fi|A/C|Steps from Winery & Golf Course
GOTL - Hot Tub - Wine Tours - Sunset Vacation Rentals
9.8 out of 10, Exceptional, (6)
"Great place!"
GOTL - Hot Tub - Wine Tours - Sunset Vacation Rentals
Lakefront Luxury 2Br/2Ba Lake View /Beach/Indoor Pool/Private balcony
10.0 out of 10, Exceptional, (239)
"The location and the vie are wonderful. The property was very clean and accommodating. Close to town and several very nice restaurants. We enjoyed Alessandro's, the Loft and Martini's while we were there. They had a wonderful pool, and it has a small beach where you could grill out have a campfire right on the water. entire property very well kept. We may get back this way some day and if so will enjoy staying here again."
Lakefront Luxury 2Br/2Ba Lake View /Beach/Indoor Pool/Private balcony
Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries
9.4 out of 10, Exceptional, (209)
"Thank you so much for allowing us to stay here for our Nationals dance competition weekend! Super close to the venue for us. Beautiful view of the lake! Great property to stay. Plan to use again for next dance season!"
Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries
Pet Friendly | A/C | Wi-Fi & Cable | Grill |Walk to Lake| Firepit | Wine Country
9.6 out of 10, Exceptional, (160)
"The place was exactly as advertised, extremely clean. Price was reasonable."
The price is NZ$288
per night
11 Jun - 12 Jun
Pet Friendly | A/C | Wi-Fi & Cable | Grill |Walk to Lake| Firepit | Wine Country
Ezmeralda's ~ Classic 1920's Renovated Bungalow ~ "A Hidden Gem of Geneva"
10.0 out of 10, Exceptional, (164)
"I've been to Ezmerelda's 3 times now and love it more each time! It's my "go to" place for time away with my best friend or boyfriend. A fire at the wine shack soothes my soul. I love watching the birds at the feeders and seeing all the wonderful plants bloom. Jan, the hostess, is a steward of wildlife and plant propagation and the gardens are simply beautiful. Lots of little restaurants, wineries, and antique shops nearby."
Ezmeralda's ~ Classic 1920's Renovated Bungalow ~ "A Hidden Gem of Geneva"
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See all available properties in Windsor
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.

Other types of properties in Windsor you may be interested in

The Lodge at Geneva
3.5 star property
9.2 out of 10, Wonderful, (491)
"Beautiful area with hiking"
The price is NZ$372
per night
4 Jun - 5 Jun
The Lodge at Geneva
Red Roof Inn Cleveland - Mentor/ Willoughby
2.0 star property
7.6 out of 10, Good, (1001)
"The beds were comfortable and the room was clean. The price affordable "
The price is NZ$139
per night
30 May - 31 May
Red Roof Inn Cleveland - Mentor/ Willoughby
Holiday Inn Express And Suites Painesville - Concord, an IHG Hotel
2.5 star property
9.4 out of 10, Exceptional, (673)
"Hotel was very new and very clean. Bed was super comfortable. Breakfast was nice."
The price is NZ$280
per night
4 Jun - 5 Jun
Holiday Inn Express And Suites Painesville - Concord, an IHG Hotel
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Windsor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Windsor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Windsor. Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Windsor short-term rentals, that won’t be hard to do.

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 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 Nelson-Kennedy Ledges State Park. Windsor Mills Covered Bridge and Grand River Cellars Winery 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.

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