Holiday Rentals in Windsor

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Holiday Rentals in Windsor

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

Geneva
9.6 out of 10, Exceptional, (111)
"Enjoyed our stay! Great location!"
United States
A guest from Pittsburgh, PA L.
Great Strip Location | Walk to Lake|Wine Country|A/C|Fireplace|Family Friendly

LAKEFRONT LOFT-PERFECT COUPLES GETAWAY--rent 2 get 3rd free-until April 1- ask!

Geneva
10.0 out of 10, Exceptional, (362)
"Very clean and thanks to Debbie for great communication and the suggestion on The Little Pie shop for breakfast it was fantastic !! "
United States
jeff
The price is €133
includes taxes & fees
30 Nov - 1 Dec
LAKEFRONT LOFT-PERFECT COUPLES GETAWAY--rent 2 get 3rd free-until April 1- ask!

3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.

Rome
10.0 out of 10, Exceptional, (22)
"Wonderful cabin and owners. Easily a 5/5 with lots of things to do near by"
United States
Connor
The price is €184
includes taxes & fees
27 Nov - 28 Nov
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.

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

Geneva
9.8 out of 10, Exceptional, (84)
"Very clean rental, responsive host and convenient location."
United States
Harry Z.
Modern 2B Family Home Near Wine Country- 6m Walk to Lake +Pet Friendly

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

Geneva
9.4 out of 10, Exceptional, (104)
"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!"
United States
Diane
Great Strip Location|WalktoLake|Wine Country|AC|Grill&Firepit|FamilyFriendly

Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Burton
10.0 out of 10, Exceptional, (47)
"I have stayed here before and enjoyed it just as much the second time. The place had a lot of charm, was very clean and was very convenient to where I was working. I will stay there again. "
United States
Kathryn
The price is €101
includes taxes & fees
30 Nov - 1 Dec
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Cabin 1 The Sunrise Patio

Geneva
9.6 out of 10, Exceptional, (7)
"Atmosphere cabin property and hosts where exceptional!Recommend contacting host before booking they are off grid (no electric, running water or sewer) "
United States
Lora S.
The price is €137
includes taxes & fees
27 Dec - 28 Dec
Cabin 1 The Sunrise Patio

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

Geneva
9.4 out of 10, Exceptional, (325)
"This was the cleanest rental we have stayed in! We enjoyed the deck w the water views."
United States
Tamara E.
Lakefront Home Water Front Pet Friendly Steps from Winery Wi-Fi & Cable

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

Geneva-on-the-Lake
9.4 out of 10, Exceptional, (246)
"Always a great to place to stay. Close to everything!"
United States
Julie S.
Center of Strip |Pet Friendly|A/C|Wi-fi & Cable|Stately Home|Steps from Winery

Keys cottage -walk to the strip,Private lot, 2bdr 3rd guestroom detached.Spire

Geneva
10.0 out of 10, Exceptional, (105)
"Beautiful cottage just as described. Will stay again."
United States
Anonymous traveller
The price is €183
includes taxes & fees
3 Dec - 4 Dec
Keys cottage -walk to the strip,Private lot, 2bdr 3rd guestroom detached.Spire

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

Geneva
9.6 out of 10, Exceptional, (258)
"Nice place, will stay again "
United States
Patrick H.
Main Strip Location | Pet Friendly | Wi-Fi & Cable | A/C | Steps from Winery

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

Geneva
9.8 out of 10, Exceptional, (205)
"Great place"
United States
Garrett W.
Great Strip Location | Lake View | Pet Friendly | A/C | Sauna| Wine Country|WiFi

East End of The Strip. A/C Wifi Cable TV Firepit Walk to Park/Lake Wineries

Geneva
9.6 out of 10, Exceptional, (90)
"Nice house and great location!"
United States
Lana N.
East End of The Strip. A/C Wifi Cable TV Firepit Walk to Park/Lake Wineries

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

Geneva
9.2 out of 10, Wonderful, (82)
"Easy check in, great location."
United States
Roxanne B.
Great Strip Location |WalktoLake|Wine Country|Brewing Company|A/C|Grill&Firepit

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

Geneva
9.4 out of 10, Exceptional, (222)
"Location was perfect! Furnitue was all liquidation hotel items"
United States
Tracey
The price is €128
includes taxes & fees
27 Nov - 28 Nov
Center Strip Location|Pet Friendly|Wi-Fi|A/C|Steps from Winery & Golf Course

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

Geneva
9.4 out of 10, Exceptional, (93)
"Great location, clean and well equipped. "
United States
Stephanie C.
East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly

A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!

Geneva
10.0 out of 10, Exceptional, (8)
"Loved this property. Was so clean and nice. "
United States
Allyson C.
The price is €169
includes taxes & fees
30 Nov - 1 Dec
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!

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

Geneva
9.8 out of 10, Exceptional, (23)
"Wonderful ambience and lovely stay!"
United States
Daniel
Linny's GOTL Cottages "Lazy Days" Charming 2-bedroom bungalow with AC, GOTL.

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

Geneva
10.0 out of 10, Exceptional, (105)
"Perfect place ! Cozy and comfy ! Amazing host ! "
United States
Roberta T.
The price is €190
includes taxes & fees
30 Nov - 1 Dec
Beautiful newly remodeled cottage - Walk to strip, close to spire

Charming 1-bedroom cabin in Geneva

Geneva
9.8 out of 10, Exceptional, (7)
"The cabin was definitely peacful i enjoyed the nature it was an amazing experience the host were friendly an very welcoming "
United States
Kenzie C.
Charming 1-bedroom cabin in Geneva
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?

Modern 2B Family Home Near Wine Country- 6m Walk to Lake +Pet Friendly: This holiday home rental outside of Windsor is located on a lake, and has a fireplace, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Munson Township Park. Windsor Mills Covered Bridge and Huntsburg Town Hall 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.