A wooden covered bridge over a river surrounded by lush greenery.

Windsor Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Windsor holiday rentals

Dining

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

3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
Rome
10.0 out of 10, Exceptional, (44 reviews)
"Wonderful place! We all want to go back for a longer stay - especially when it's warm enough to enjoy the screened in porch."
United States
Laura M.
The price is HK$1,058
HK$1,725 total
includes taxes & fees
20 Jul - 21 Jul
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
Exterior

Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (97 reviews)
"Absolutely perfect. Beautiful country home on a farm. Would 100% recommend and stay again. Amish store and restaurant just minutes away. Hosts left snacks and a variety of coffee and creamer choices. WiFi was great too as I had very little cell phone reception on the property. "
United States
Megan
The price is HK$1,215
HK$1,795 total
includes taxes & fees
20 Jul - 21 Jul
Little house on the farm
Smart TV, fireplace

Conveniently located 2 bedroom home only minutes from hiking and state park fun!

Conveniently located 2 bedroom home only minutes from hiking and state park fun!
Warren
10.0 out of 10, Exceptional, (137 reviews)
"Great stay and amazing host"
United States
Raven S.
The price is HK$748
HK$1,398 total
includes taxes & fees
21 Jul - 22 Jul
Conveniently located 2 bedroom home only minutes from hiking and state park fun!
2 bedrooms, free WiFi, bed sheets

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

A great stay, close to Spire, GOTL, & Wineries....King Bed!
Geneva
10.0 out of 10, Exceptional, (42 reviews)
"Great stay"
United States
Freeman H.
The price is HK$769
HK$1,592 total
includes taxes & fees
19 Jul - 20 Jul
A great stay, close to Spire, GOTL, & Wineries....King Bed!
Living area

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

A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
Geneva
10.0 out of 10, Exceptional, (15 reviews)
"Good stay"
Canada
Corey
The price is HK$769
HK$1,647 total
includes taxes & fees
20 Jul - 21 Jul
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
Terrace/patio

Tiny Haven

Tiny Haven
Kinsman
10.0 out of 10, Exceptional, (30 reviews)
"The property was beautiful, the host was very generous and sweet, and it was overall, just a nice and relaxing place to get away from it all."
United States
Victor H.
The price is HK$980
HK$1,795 total
includes taxes & fees
19 Jul - 20 Jul
Tiny Haven
Terrace/patio

Cabin 1 The Sunrise Patio

Cabin 1 The Sunrise Patio
Geneva
9.0 out of 10, Wonderful, (13 reviews)
"Very easy, inconvenient check-in, a quiet and comfortable little area with plenty of options of things to do if you plan to stay for more than a few days. Also very accommodating to quick one night stays if needed."
United States
Joseph S.
The price is HK$784
HK$995 total
includes taxes & fees
3 Aug - 4 Aug
Cabin 1 The Sunrise Patio
Exterior

Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Burton
10.0 out of 10, Exceptional, (62 reviews)
"Wonderful stay. It was clean, nice area, nice view, fun decor. Bed was comfortable. Good privacy."
United States
O'Neill
The price is HK$882
HK$1,313 total
includes taxes & fees
28 Jul - 29 Jul
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Property grounds

Charming GOTL 1 Bedroom Lake Erie Cottage, sleeps 4

Charming GOTL 1 Bedroom Lake Erie Cottage, sleeps 4
Geneva
10.0 out of 10, Exceptional, (32 reviews)
"Very nice place, check it out!"
United States
Christopher D.
The price is HK$905
HK$1,933 total
includes taxes & fees
23 Jul - 24 Jul
Charming GOTL 1 Bedroom Lake Erie Cottage, sleeps 4
Property grounds

Charming 1-bedroom cabin in Geneva

Charming 1-bedroom cabin in Geneva
Geneva
9.8 out of 10, Exceptional, (8 reviews)
"Great out of the grid hideaway. Hosts are very nice, thanks for having us! "
United States
nina H.
The price is HK$882
HK$1,074 total
includes taxes & fees
28 Jul - 29 Jul
Charming 1-bedroom cabin in Geneva
Property grounds

Cozy Shed-Teau in Geneva + Firepit

Cozy Shed-Teau in Geneva + Firepit
Geneva
9.4 out of 10, Exceptional, (10 reviews)
"Your place was beautiful. Unfortunately we did not get to spend the night as planned. Thank you."
United States
Lori S.
The price is HK$949
HK$1,207 total
includes taxes & fees
21 Jul - 22 Jul
Cozy Shed-Teau in Geneva + Firepit
Free WiFi, bed sheets

Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat

Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
Madison
9.6 out of 10, Exceptional, (5 reviews)
"This was an incredible stay for my wife and I. The cleanliness, quietness, and coziness was amazing. We will definitely be back for another anniversary stay. The multiple wineries around also help enhance the stay even more. You’re missing out if you don’t book this cabin. "
United States
Matthew
The price is HK$1,638
HK$1,873 total
includes taxes & fees
19 Jul - 20 Jul
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
Interior

Nestled Inn Mespo Modern & Cozy Apartment

Nestled Inn Mespo Modern & Cozy Apartment
Middlefield
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful place and very well taken care of."
United States
Andrew G.
The price is HK$1,176
HK$1,607 total
includes taxes & fees
19 Jul - 20 Jul
Nestled Inn Mespo Modern & Cozy Apartment
Outdoor spa tub

Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far

Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
Madison
9.6 out of 10, Exceptional, (9 reviews)
"Super clean and cozy cabin! I can’t wait to stay again! "
United States
Alyssa T.
The price is HK$1,638
HK$1,873 total
includes taxes & fees
19 Jul - 20 Jul
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
Private kitchen

Peaceful private apartment in the charming Hiram countryside

Peaceful private apartment in the charming Hiram countryside
Garrettsville
9.2 out of 10, Wonderful, (5 reviews)
"We had a wonderful experience! The bed was very comfortable and the space was beautiful and clean. We enjoyed how quiet the area was and it was perfect for our weekend getaway. We will absolutely be staying here the next time we are out this way!"
United States
Ashley
The price is HK$705
HK$1,495 total
includes taxes & fees
17 Jul - 18 Jul
Peaceful private apartment in the charming Hiram countryside
Exterior

BB Hideaway

BB Hideaway
Geneva
9.2 out of 10, Wonderful, (5 reviews)
"We had a wonderful time place was beautiful!! Very clean! Owners were amazing above and beyond 10000/10000 definitely coming back! Thank you guys so much !!"
United States
Paige M.
The price is HK$882
HK$1,074 total
includes taxes & fees
28 Jul - 29 Jul
BB Hideaway
TV

1br-1bth- Furnished Apartment in Chardon

1br-1bth- Furnished Apartment in Chardon
Chardon
9.6 out of 10, Exceptional, (14 reviews)
"The apartment was very nice and the hosts appointed it very well. It is a great place to stay!"
United States
Eric M.
The price is HK$980
HK$1,215 total
includes taxes & fees
28 Jul - 29 Jul
1br-1bth- Furnished Apartment in Chardon
On the beach

LemonDrop Lake-Front Cottage

LemonDrop Lake-Front Cottage
Madison-on-the-Lake
10.0 out of 10, Exceptional, (17 reviews)
"Wife and I had a memorable stay at this charming cottage right on Lake Erie. The owners were extremely gracious and accommodating. Highly recommend for a relaxing get away!"
United Kingdom
Daniel C.
The price is HK$1,395
HK$2,265 total
includes taxes & fees
23 Jul - 24 Jul
LemonDrop Lake-Front Cottage
Interior

The Riesling Cottage - GOTL Strip - Cozy & Quaint

The Riesling Cottage - GOTL Strip - Cozy & Quaint
Geneva
10.0 out of 10, Exceptional, (24 reviews)
"Very nice, clean.and cozy cottage. Would recommend to everyone. "
United States
David R
The price is HK$768
HK$2,507 total
includes taxes & fees
2 Aug - 3 Aug
The Riesling Cottage - GOTL Strip - Cozy & Quaint
Coffee/tea maker, fridge, microwave, oven

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

Recently updated apartment in a Triplex unit #1 close to wineries and the lake.
Geneva
9.6 out of 10, Exceptional, (39 reviews)
"Everything was as described. It was a pleasant visit."
United States
Amy
The price is HK$938
HK$1,612 total
includes taxes & fees
27 Jul - 28 Jul
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

Red Roof Inn Cleveland - Mentor/ Willoughby

Red Roof Inn Cleveland - Mentor/ Willoughby

8/10 Good
"."
James 2-night trip
Posted 3 hours ago
Red Roof Inn Cleveland - Mentor/ Willoughby

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

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  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

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?

Walk to Lake, Park & Strip | Pet Friendly: This holiday home rental outside of Windsor is located on a lake, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and an oven, so that 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 Snow Lake. Windsor Mills Covered Bridge and Rothenbühler Cheese Chalet 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.