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

Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Windsor vacation rentals

Exterior

1. Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (97 reviews)
"Great location to enjoy some peaceful country living!"
United States
Jerry L.
$228 nightly
The price is $228
Aug 6 - Aug 7
Total with taxes and fees
Little house on the farm
Dining

2. 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, (45 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.
$191 nightly
The price is $199
Aug 25 - Aug 26
Total with taxes and fees
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
Interior

3. Nestled Inn Mespo Modern & Cozy Apartment

Nestled Inn Mespo Modern & Cozy Apartment
Middlefield
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful place and very well taken care of."
United States
Andrew G.
$205 nightly
The price is $205
Aug 6 - Aug 7
Total with taxes and fees
Nestled Inn Mespo Modern & Cozy Apartment
Exterior

4. 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, (64 reviews)
"Wonderful stay. It was clean, nice area, nice view, fun decor. Bed was comfortable. Good privacy."
United States
O'Neill
$162 nightly
The price is $162
Aug 11 - Aug 12
Total with taxes and fees
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Terrace/patio

5. Tiny Haven

Tiny Haven
Kinsman
10.0 out of 10, Exceptional, (31 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.
$228 nightly
The price is $228
Aug 6 - Aug 7
Total with taxes and fees
Tiny Haven
Smart TV, fireplace

6. 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, (138 reviews)
"Perfect location for us to stay while visiting family! Very clean and easy to find! Quiet location."
United States
Danielle
$188 nightly
The price is $188
Aug 10 - Aug 11
Total with taxes and fees
Conveniently located 2 bedroom home only minutes from hiking and state park fun!
Terrace/patio

7. Cabin 1 The Sunrise Patio

Cabin 1 The Sunrise Patio
Geneva
9.0 out of 10, Wonderful, (14 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.
$120 nightly
The price is $127
Aug 10 - Aug 11
Total with taxes and fees
Cabin 1 The Sunrise Patio
Outdoor spa tub

8. 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, (10 reviews)
"Super clean and cozy cabin! I can’t wait to stay again! "
United States
Alyssa T.
$227 nightly
The price is $227
Aug 11 - Aug 12
Total with taxes and fees
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
Living area

9. 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, (16 reviews)
"Good stay"
Canada
Corey
$210 nightly
The price is $210
Aug 9 - Aug 10
Total with taxes and fees
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
2 bedrooms, WiFi (free), bed sheets

10. 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, (43 reviews)
"Very clean.. spacious, Close to wineries."
United States
frances f.
$206 nightly
The price is $206
Aug 9 - Aug 10
Total with taxes and fees
A great stay, close to Spire, GOTL, & Wineries....King Bed!
Property grounds

11. 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.
$135 nightly
The price is $140
Aug 10 - Aug 11
Total with taxes and fees
Charming 1-bedroom cabin in Geneva
Property grounds

12. Cozy Shed-Teau in Geneva + Firepit

Cozy Shed-Teau in Geneva + Firepit
Geneva
9.6 out of 10, Exceptional, (11 reviews)
"Every detail was thought of, from the comfortable bedding to the well-appointed outdoor area."
United States
Stephen S.
$143 nightly
The price is $143
Aug 10 - Aug 11
Total with taxes and fees
Cozy Shed-Teau in Geneva + Firepit
Exterior

13. BB Hideaway

BB Hideaway
Geneva
9.2 out of 10, Wonderful, (7 reviews)
"Had a great experience Teresa was helping at showing around the area. We stayed at the stargazer and it was a cute romantic get away."
United States
Aimee
$133 nightly
The price is $137
Aug 10 - Aug 11
Total with taxes and fees
BB Hideaway
WiFi (free), bed sheets

14. 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
$227 nightly
The price is $227
Aug 13 - Aug 14
Total with taxes and fees
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
TV

15. 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.
$155 nightly
The price is $155
Aug 9 - Aug 10
Total with taxes and fees
1br-1bth- Furnished Apartment in Chardon
Property grounds

16. Pet Friendly | Walk to Lake | Firepit & Grill

Pet Friendly | Walk to Lake | Firepit & Grill
Geneva
9.6 out of 10, Exceptional, (226 reviews)
"We thought it was perfect for what we needed 2 dogs And a nice park around corner Perfect place!!"
United States
Scott
$237 nightly
The price is $254
Aug 6 - Aug 7
Total with taxes and fees
Pet Friendly | Walk to Lake | Firepit & Grill
Interior

17. 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
$287 nightly
The price is $293
Aug 26 - Aug 27
Total with taxes and fees
The Riesling Cottage - GOTL Strip - Cozy & Quaint
Private kitchen

18. 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
$188 nightly
The price is $190
Aug 10 - Aug 11
Total with taxes and fees
Peaceful private apartment in the charming Hiram countryside
Property grounds

19. Center Strip | Pets OK | Wi-Fi | Near Wineries

Center Strip | Pets OK | Wi-Fi | Near Wineries
Geneva
9.4 out of 10, Exceptional, (251 reviews)
"Great location, clean & cozy!"
United States
Michele
$173 nightly
The price is $185
Aug 24 - Aug 25
Total with taxes and fees
Center Strip | Pets OK | Wi-Fi | Near Wineries
Property grounds

20. 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.
$236 nightly
The price is $267
Aug 6 - Aug 7
Total with taxes and fees
Charming GOTL 1 Bedroom Lake Erie Cottage, sleeps 4
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

The Lodge at Geneva-on-the-Lake

The Lodge at Geneva-on-the-Lake

8/10 Good
"Last summer we really enjoyed the bikes. You could pick your own bike and they were located close to the property. This year they are given to you at the zip line location. My grandsons and we did not like the bikes we were assigned. They seem more focused an the E bikes and scooters. That was sad for us as I said we really enjoyed them in the past. Truthfully it impacted the fun we had and it was not quite as an enjoyable visit."
Patricia 1-night trip
Posted 10 hours ago
The Lodge at Geneva-on-the-Lake

Find out more about Windsor

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $43 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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?

Lake Access Retreat Pet Friendly Fire Pit: This vacation home rental outside of Windsor is located on a lake and has a fireplace, a balcony, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden.

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 Century Village Museum 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.