Windsor Holiday Rentals

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Check prices for these dates

Holiday Rentals in Windsor

Charming centrally located 3-bedroom cottage in Geneva with WiFi and AC

10.0 out of 10, Exceptional, (1)
"Wonderful place, they were super accommodating and quick to respond! Made our Valentine’s Day super special!! Thank uou so much for the awesome amenities!! We will be back!"
The price is AU$465
includes taxes & fees
23 Feb - 24 Feb
Charming centrally located 3-bedroom cottage in Geneva with WiFi and AC

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

9.4 out of 10, Exceptional, (299)
"This was our second time staying at this property. Once again it was a great time. The house is super clean and comfortable. Matt is always responsive to my questions. We would definitely stay here again. "
Lakefront Home|Water Access| Pet Friendly| Steps from Winery|Wi-Fi & Cable|A/C

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

9.4 out of 10, Exceptional, (232)
"Took a trip with family and friends for my birthday. Location was perfect. Best part of this location was that everyone was able to have their own room. "
Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries

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

9.6 out of 10, Exceptional, (109)
"I stayed at this property with my family over a weekend in October and it was awesome. Here are some things we loved about the property: - Space: the cabins sit on a plot of land overlooking the lake. There's plenty of space for cars (we had 5) and for recreation. We set up corn hole, games for the kids, etc. and had ample room to play. There's a nice patio between two cabins where we spent a lot of time. We grilled out, sat by the fire pit in the evening and, in general, enjoyed being outside....
3Cottages on Strip, Lakefront, AC, WiFi, Fire pit, Deck over Lake, Pet Friendly

beautiful newly remodeled cottage - Walk to strip close to spire

10.0 out of 10, Exceptional, (71)
"This property was nothing short of incredible. Beautifully renovated, clean, and only a short driving distance to the wineries. We had a wonderful time! Would highly recommend this property to future guests!"
The price is AU$296
includes taxes & fees
20 Feb - 21 Feb
beautiful newly remodeled cottage - Walk to strip close to spire

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

9.8 out of 10, Exceptional, (182)
"We had a great time! We had 8 adults and 6 kiddos and we had plenty of room! We had plenty of everything we needed. There is a regular drip coffee pot and one for k-cups. Many of the shops and restaurants in GOTL are closed in the winter. We would love to see how the city transforms in the summer! "
Great Strip Location | Lake View | Pet Friendly | A/C | Sauna| Wine Country|WiFi

Lakefront - Winery - GOTL Oasis- Sunset Vacation Rentals

9.4 out of 10, Exceptional, (51)
"Beautiful views of the lake and all the stacking ice was amazing ! Over all a great stay. Only issues was dog hair left by a previous guest and a patio door wouldn’t lock. Would love to come back in the summer. "
Lakefront - Winery - GOTL Oasis- Sunset Vacation Rentals

Endless Summer - Sleeps 6 Condo

10.0 out of 10, Exceptional, (81)
"Wonderful stay"
Endless Summer - Sleeps 6 Condo

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

9.6 out of 10, Exceptional, (209)
"This was a cute cottage ! On the smaller side but was cute and had everything we needed ! Nice bedding and towels ! "
Strip Location | Pet Friendly | A/C | Wi-Fi & Cable | Fire Pit | Wine Country

Cottage on Strip w/ 3 BDs, Newly Renovated, Pet Friendly Wifi,AC,Grill, Fire Pit

9.2 out of 10, Wonderful, (41)
"The house as very clean, check in process was extremely easy and everything was just as listed. There a was an issue with the bedroom shower but I text the owner and within 15 minutes maintenance was there to fix the issue. I would definitely book this place again! "
Cottage on Strip w/ 3 BDs, Newly Renovated, Pet Friendly Wifi,AC,Grill, Fire Pit

Lakefront Luxury 2Br/2Ba Lake View /Beach/Indoor Pool/Private balcony

10.0 out of 10, Exceptional, (262)
"We enjoyed our mini winter escape the condo met and exceeded all of our needs. The unit was very clean spacious and we could not have enjoyed it more! The owners and property manager were wonderful and very responsive. I would absolutely re book this unit."
Lakefront Luxury 2Br/2Ba Lake View /Beach/Indoor Pool/Private balcony

LAKEFRONT LOFT-PERFECT COUPLES GETAWAY Rent 2 /3rd free until May 22--ask!

10.0 out of 10, Exceptional, (320)
"The house was awesome and the place was beautiful totally fit our needs for a couples retreat"
The price is AU$254
includes taxes & fees
20 Mar - 21 Mar
LAKEFRONT LOFT-PERFECT COUPLES GETAWAY Rent 2 /3rd free until May 22--ask!

April Morning, Spectacular Lakefront, 3BD 3 BA, Off Season REDUCED RATES, ASK !!

10.0 out of 10, Exceptional, (19)
"Took our mothers who are 82 and 85 here for Christmas. Beautiful accommodations. Lots of space, great views"
April Morning, Spectacular Lakefront, 3BD 3 BA, Off Season REDUCED RATES, ASK !!

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

9.6 out of 10, Exceptional, (229)
"Was in town for a 4 day swim meet.Stayed in a hotel the previous year but wanted a little more personable home like feel.Great location with all the comforts of home.Will stay again for sure the next time we are in the area!….highly recommend!"
Main Strip Location | Pet Friendly | Wi-Fi & Cable | A/C | Steps from Winery

Great Strip Location | Walk to Lake|Wine Country|A/C|Fireplace|Family Friendly

9.6 out of 10, Exceptional, (93)
"Perfect size for group of eight."
Great Strip Location | Walk to Lake|Wine Country|A/C|Fireplace|Family Friendly

Little oasis a short walk from GOTL strip

10.0 out of 10, Exceptional, (75)
"We loved our stay at this charming little getaway! The property truly lives up to its name—a cozy, peaceful retreat that’s just a short walk from the heart of the GOTL strip. The location couldn’t be better: close enough to enjoy the lively atmosphere of the area but tucked away enough to feel like your own private hideaway. The house was spotless and well-stocked with everything we needed. The décor was warm and inviting, making it feel like home from the moment we walked in. We especially...
The price is AU$315
includes taxes & fees
20 Feb - 21 Feb
Little oasis a short walk from GOTL strip

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

9.0 out of 10, Wonderful, (77)
"Close to everything. Nice fire pit."
Great Strip Location | Walk to Lake| Wine Country | A/C | Grill & Firepit

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

10.0 out of 10, Exceptional, (190)
"Very cozy."
DewDrop Cottage: Walk to the strip! 2 bed 1 bath, sleeps 5

Luxury Lakeside Cottage- Girls Getaway - 5 mi to GOTL w/ Backyard & Fire pit

10.0 out of 10, Exceptional, (39)
"Very clean and real close to the lake!! It was everything that the details said it was! I will definitely come back and stay there!!! Thank you!!!"
Luxury Lakeside Cottage- Girls Getaway - 5 mi to GOTL w/ Backyard & Fire pit

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

9.4 out of 10, Exceptional, (224)
"House was great. Lots of room. Was perfect for adults, not too many bunk beds or single beds, that adults do not want to sleep in. Close to strip and easy drive to most of the wineries. Perfect for large group we had 11 adults and still had extra rooms. Has everything you could need!"
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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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, (632)
"My husband and I booked a trip in the winter. There weren’t as many options open in town but we made the best of our trip. Dinner at the hotel restaurant was tasty, rinks were delicious, and the staff were amazing. A snow storm came during our visit and we needed to book an extra night. The staff could not have been more helpful and accommodating. "
The price is AU$275
includes taxes & fees
20 Feb - 21 Feb
The Lodge at Geneva

Red Roof Inn Cleveland - Mentor/ Willoughby

2.0 star property
7.4 out of 10, Good, (1001)
"Good value"
The price is AU$110
includes taxes & fees
26 Feb - 27 Feb
Red Roof Inn Cleveland - Mentor/ Willoughby

Comfort Inn

2.5 star property
8.4 out of 10, Very good, (874)
"Exceptionally clean room even in the middle of construction. We were in the middle of a snow storm and the staff were amazingly helpful. Breakfast was great. Pool very nice. Can't wait to see it when done. "
The price is AU$157
includes taxes & fees
5 Mar - 6 Mar
Comfort Inn
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.

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 Middlefield Cheese Chalet Shop, or get outside and enjoy nature at Nelson-Kennedy Ledges State Park. 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.