Windsor Vacation Rentals

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Vacation Rentals in Windsor

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
Great Strip Location|Walk to Lake|Wine Country|A/C| Grill & Firepit|Family.
9.6 out of 10, Exceptional, (48)
"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!"
Great Strip Location|Walk to Lake|Wine Country|A/C| Grill & Firepit|Family.
Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C
9.4 out of 10, Exceptional, (271)
"It was a great location for relaxing with an incredible lake view or to explore GOTL. We hired a local private wine tour company ( Next Flight) and visited multiple local wineries. The only “ negative” regarding the property was that we didn’t know in advance it contains zero closets. If we book it again we will pack accordingly with clothes that aren’t intended to be hung on hangers. The streaming TV service was not very reliable, but we didn’t try to use it much at all anyway, and that seems...
The price is CA $540
CA $854 total
includes taxes & fees
Jun 27 - Jun 28
Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C
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East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly
9.4 out of 10, Exceptional, (52)
"The location was great, communication with owners was easy . Very few complaints"
The price is CA $169
CA $338 total
includes taxes & fees
Jun 16 - Jun 17
East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly
A great stay, close to Spire, GOTL, & Wineries....King Bed!
10.0 out of 10, Exceptional, (5)
"We had a great stay. Very clean and a cute place. Five minutes from strip and within ten miles of all surrounding wineries if not closer. "
The price is CA $135
CA $277 total
includes taxes & fees
Jun 11 - Jun 12
A great stay, close to Spire, GOTL, & Wineries....King Bed!
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."
The price is CA $67
CA $154 total
includes taxes & fees
Jun 16 - Jun 17
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, (168)
"This little cottage served all of our needs during our stay in Geneva on the Lake! It is located just steps away from the strip! Very convenient!"
The price is CA $67
CA $208 total
includes taxes & fees
Jun 9 - Jun 10
Center Strip Location|Pet Friendly|Wi-Fi|A/C|Steps from Winery & Golf Course
Lakefront Luxury 2Br/2Ba Lake View /Beach/Indoor Pool/Private balcony
10.0 out of 10, Exceptional, (240)
"Nice clean beautiful lake view"
Lakefront Luxury 2Br/2Ba Lake View /Beach/Indoor Pool/Private balcony
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 CA $238
CA $448 total
includes taxes & fees
Jun 5 - Jun 6
DewDrop Cottage: Walk to the strip! 2 bed 1 bath, sleeps 5
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
New Remodel |Close Lake&Park|Wine Country|Family/Pet Friendly|A/C|Wi-FiCable
8.8 out of 10, Excellent, (67)
"My wife and I stayed Here for her birthday weekend. Despite the amazing view of the lake right across the street, the atmosphere alone was stunning. The bar next door play country music live. I love Country music and my wife loves live bands regardless of what they are singing! The place in general was amazing. I am a Minimalist so walking into a place very clean, fully equipped and spacious is all I ask for in a place. THIS MAN PLACE IS IT! I was able to still work (paper/job computer work) in...
New Remodel |Close Lake&Park|Wine Country|Family/Pet Friendly|A/C|Wi-FiCable
Modern 2B Family Home Near Wine Country- 6m Walk to Lake +Pet Friendly
10.0 out of 10, Exceptional, (15)
"Property as listed and very comfortable. We had an extra person potentially staying that was not in our original booking and they gave us no issue and never even tried to charge extra. We ended up not having an extra person, but it was nice to have the option without the looming extra fee."
Modern 2B Family Home Near Wine Country- 6m Walk to Lake +Pet Friendly
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
Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries
9.4 out of 10, Exceptional, (209)
"Always love our stay at Edgewater. Great accommodations for a crowd, good commutation with Matt, and the village is a blast. A thousand stars."
Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries
walk to the strip, close to SPIRE. Private lot, 2bdr 3rd guestroom detached.
10.0 out of 10, Exceptional, (60)
"Keys Cottage has definate vacation vibes. Cozy, relaxing and fun. This is our second time staying at Keys Cottage and will stay again. Great family memories!"
The price is CA $307
CA $496 total
includes taxes & fees
Jun 17 - Jun 18
walk to the strip, close to SPIRE. Private lot, 2bdr 3rd guestroom detached.
Pet Friendly | A/C | Wi-Fi & Cable | Grill |Walk to Lake| Firepit | Wine Country
9.6 out of 10, Exceptional, (161)
"The place was exactly as advertised, extremely clean. Price was reasonable."
Pet Friendly | A/C | Wi-Fi & Cable | Grill |Walk to Lake| Firepit | Wine Country
beautiful newly remodeled cottage - Walk to strip close to spire
10.0 out of 10, Exceptional, (37)
"Everything was perfect. I would recommend to anyone."
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, (204)
"Came up for our anniversary and had a nice stay. Several restaurants close within walking distance"
The price is CA $117
CA $267 total
includes taxes & fees
Jun 19 - Jun 20
Main Strip Location | Pet Friendly | Wi-Fi & Cable | A/C | Steps from Winery
Mid Century Guest House on Wooded Lot
10.0 out of 10, Exceptional, (25)
"This property is absolutely wonderful. Beautiful and quiet."
Mid Century Guest House on Wooded Lot
Glamorous Camping - Hot Tub - GOTL - Sunset Vacation Rentals
9.6 out of 10, Exceptional, (54)
"We had a nice relaxing weekend getaway over Memorial Day. It is close enough to everything. AC worked great! The hot tub was a welcome addition and everything was very clean. Our ONLY issue was the small amount of hot water. Other than that, will stay again."
Glamorous Camping - Hot Tub - GOTL - Sunset Vacation Rentals
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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, (495)
"Beautiful lodge! Loved the room and the balcony. Fantastic pool and lots of things to do like hiking and wine tours. "
The price is CA $280
CA $342 total
includes taxes & fees
Jun 5 - Jun 6
The Lodge at Geneva
Red Roof Inn Cleveland - Mentor/ Willoughby
2.0 star property
7.6 out of 10, Good, (1010)
"Always a nice stay!"
The price is CA $102
CA $118 total
includes taxes & fees
Jun 10 - Jun 11
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, (675)
"nice clean hotel. Indoor pool and exercise room were nice (no hot tub though). good breakfast."
The price is CA $207
CA $239 total
includes taxes & fees
Jun 24 - Jun 25
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.

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor vacation rentals we have selected for you start as low as CA $67 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 vacation 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 vacation.

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 vacation rentals in Windsor?

Yes, we have vacation rentals near top local attractions in Windsor, or you can select a secluded option if you're looking for relaxation.

What are some of the best vacation home rentals in Windsor?

East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly: This vacation home rental outside of Windsor is located on a lake and has a patio, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and an oven, so you can cook with friends or family.

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 larger area.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned accommodations you can reserve for a short or long stay in Windsor. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family getaway.

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