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Top Holiday Rentals in Windsor

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

10.0 out of 10, Exceptional, (346)
"Clean, nice updated shower and quiet but quick trip to many bars and restaurants."
LAKEFRONT LOFT-PERFECT COUPLES GETAWAY--rent 3 get 4th free 10/1-12/20-just ask!

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

9.0 out of 10, Wonderful, (93)
"The property was very clean and cozy. Location was good. Will return, perhaps summer months when the strip is more active"
The price is £121
includes taxes & fees
7 Sept - 8 Sept
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, (198)
"Great place would stay again!"
DewDrop Cottage: Walk to the strip! 2 bed 1 bath, sleeps 5

Clean & Cozy Cottage - Lake Views + Private Hot Tub

9.8 out of 10, Exceptional, (19)
"Nice and helpful owners"
Clean & Cozy Cottage - Lake Views + Private Hot Tub

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

10.0 out of 10, Exceptional, (13)
"It was very clean and cozy. Linney was great to deal with."
The price is £148
includes taxes & fees
18 Aug - 19 Aug
Linny's GOTL Cottages "Lazy Days" Charming 2-bedroom bungalow with AC, GOTL.

Charming 1-bedroom cabin in Geneva

10.0 out of 10, Exceptional, (4)
"Was amazing! We will definitely be back!"
The price is £107
includes taxes & fees
11 Aug - 12 Aug
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, (249)
"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

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

8.6 out of 10, Excellent, (61)
"It was a perfect little house for me an my 9 year old to stay in for the weekend of her dance competition!"
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.

9.4 out of 10, Exceptional, (76)
"Cabin was so cute would live to rent this in the future. "
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, (312)
"enjoyed our stay"
The price is £421
includes taxes & fees
28 Aug - 29 Aug
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, (193)
"It was a convenient location to the strip and the parks. "
Pet Friendly | A/C | Wi-Fi & Cable | Grill |Walk to Lake| Firepit | Wine Country

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

9.2 out of 10, Wonderful, (72)
"We really enjoyed it, had a great time We always enjoy Eagle Cliff Inn "
Great Strip Location |WalktoLake|Wine Country|Brewing Company|A/C|Grill&Firepit

Geneva, Direct Lakefront, Hot Tub, Ohio's Wine Country

10.0 out of 10, Exceptional, (162)
"We absolutely loved our stay. The home was so incredibly beautiful and well kept and the view is something you cannot explain until you see it for yourself."
Geneva, Direct Lakefront, Hot Tub, Ohio's Wine Country

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

10.0 out of 10, Exceptional, (195)
"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

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 £166
includes taxes & fees
26 Aug - 27 Aug
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.

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

9.8 out of 10, Exceptional, (50)
"We love coming to GOTL, it’s becoming our second home! The wineries, restaurants & Erie Sunsets are 2nd to none! Can’t wait to come back!"
Lakefront condo --2BR/2Bath Sleeps 4 Private beach and lake front balcony

Quaint Cozy 1-bedroom apartment in pleasant Geneva with AC, WiFi

2.0 star property
9.4 out of 10, Exceptional, (13)
"2 night stay on our way home from vacation to visit some wineries. Property was nice & clean, perfect for just the 2 of us! Everything was as described! Highly recommend!"
Quaint Cozy 1-bedroom apartment in pleasant Geneva with AC, WiFi

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

10.0 out of 10, Exceptional, (90)
"Linny was very accommodating and personable. The house was very clean and inviting. We enjoyed our weekend stay."
The price is £207
includes taxes & fees
10 Sept - 11 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)
"Owners were great to communicate and very accommodating!"
Main Strip Location | Pet Friendly | Wi-Fi & Cable | A/C | Steps from Winery

Recently updated apartment in a Triplex unit #1 close to wineries and the lake.

9.8 out of 10, Exceptional, (27)
"Was a short stay and easy to find "
Recently updated apartment in a Triplex unit #1 close to wineries and the lake.
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

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.