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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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.
$229 nightly
The price is $229
Aug 31 - Sep 1
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, (53 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.
$209 nightly
The price is $218
Sep 2 - Sep 3
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, (11 reviews)
"Beautiful place and very well taken care of."
United States
Andrew G.
$229 nightly
The price is $229
Aug 31 - Sep 1
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, (65 reviews)
"Wonderful stay. It was clean, nice area, nice view, fun decor. Bed was comfortable. Good privacy."
United States
O'Neill
$164 nightly
The price is $164
Aug 31 - Sep 1
Total with taxes and fees
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Outdoor dining

5. Beautiful cabin situated on wooded land with nice yard clearing and small stream

Beautiful cabin situated on wooded land with nice yard clearing and small stream
Madison
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful stay :) "
United States
Jennifer S.
$165 nightly
The price is $169
Sep 18 - Sep 19
Total with taxes and fees
Beautiful cabin situated on wooded land with nice yard clearing and small stream
Living area

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, (141 reviews)
"Perfect location for us to stay while visiting family! Very clean and easy to find! Quiet location."
United States
Danielle
$176 nightly
The price is $176
Sep 8 - Sep 9
Total with taxes and fees
Conveniently located 2 bedroom home only minutes from hiking and state park fun!
Exterior

7. Romantic Woodside Cabin | Hot Tub & Fire Pit

Romantic Woodside Cabin | Hot Tub & Fire Pit
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
$275 nightly
The price is $305
Sep 13 - Sep 14
Total with taxes and fees
Romantic Woodside Cabin | Hot Tub & Fire Pit
Living area

8. 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, (19 reviews)
"Good stay"
Canada
Corey
$209 nightly
The price is $209
Aug 31 - Sep 1
Total with taxes and fees
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
Property grounds

9. 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
Sep 1 - Sep 2
Total with taxes and fees
Charming 1-bedroom cabin in Geneva
Terrace/patio

10. Tiny Haven

Tiny Haven
Kinsman
10.0 out of 10, Exceptional, (33 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.
$229 nightly
The price is $229
Aug 31 - Sep 1
Total with taxes and fees
Tiny Haven
Terrace/patio

11. Cabin 1 The Sunrise Patio

Cabin 1 The Sunrise Patio
Geneva
9.2 out of 10, Wonderful, (15 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 31 - Sep 1
Total with taxes and fees
Cabin 1 The Sunrise Patio
Private kitchen

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

Quaint Cozy 1-bedroom apartment in pleasant Geneva with AC, WiFi
Geneva
9.4 out of 10, Exceptional, (25 reviews)
"Super comfy bed, A/C was excellent, cute little 50’s style restaurant just down the road. "
United States
Stephanie
$184 nightly
The price is $193
Aug 31 - Sep 1
Total with taxes and fees
Quaint Cozy 1-bedroom apartment in pleasant Geneva with AC, WiFi
Room

13. 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, (46 reviews)
"Cute rental in a great location not far from shopping and the lake !!! Our family had a great stay here we made so many memories. The arcade was a big hit!"
United States
ceberio68
$192 nightly
The price is $192
Sep 13 - Sep 14
Total with taxes and fees
A great stay, close to Spire, GOTL, & Wineries....King Bed!
Private kitchen

14. Peaceful private apartment in the charming Hiram countryside

Peaceful private apartment in the charming Hiram countryside
Garrettsville
9.4 out of 10, Exceptional, (6 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
$189 nightly
The price is $191
Aug 31 - Sep 1
Total with taxes and fees
Peaceful private apartment in the charming Hiram countryside
Private kitchen

15. 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, (42 reviews)
"Very nice place. Nice location. Would stay there again."
United States
Kelly B.
$202 nightly
The price is $202
Sep 1 - Sep 2
Total with taxes and fees
Recently updated apartment in a Triplex unit #1 close to wineries and the lake.
Outdoor dining

16. Cozy Country Apartment in Heart of Geauga County

Cozy Country Apartment in Heart of Geauga County
Newbury
10.0 out of 10, Exceptional, (33 reviews)
"The apartment was clean, well maintained, and family friendly. Molly was a great host!"
United States
Phillip R.
$280 nightly
The price is $280
Aug 31 - Sep 1
Total with taxes and fees
Cozy Country Apartment in Heart of Geauga County
Dining

17. Country Cottage Farm Stay at Stoneycreek Acres

Country Cottage Farm Stay at Stoneycreek Acres
Newbury
10.0 out of 10, Exceptional, (75 reviews)
"Excellent communication with host and extremely clean, peaceful and beautiful place to stay "
United States
Jennifer T.
$378 nightly
The price is $378
Aug 31 - Sep 1
Total with taxes and fees
Country Cottage Farm Stay at Stoneycreek Acres
Exterior

18. 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
$151 nightly
The price is $156
Aug 31 - Sep 1
Total with taxes and fees
BB Hideaway
Property grounds

19. Cozy Shed-Teau in Geneva + Firepit

Cozy Shed-Teau in Geneva + Firepit
Geneva
9.6 out of 10, Exceptional, (12 reviews)
"Every detail was thought of, from the comfortable bedding to the well-appointed outdoor area."
United States
Stephen S.
$163 nightly
The price is $163
Sep 8 - Sep 9
Total with taxes and fees
Cozy Shed-Teau in Geneva + Firepit
Terrace/patio

20. Walk to Lake & Strip | Firepit & Grill

Walk to Lake & Strip | Firepit & Grill
Geneva
8.8 out of 10, Excellent, (114 reviews)
"Inside was cute and cozy. Perfect for my husband and I. Strip was in easy walking distance. Bed was comfortable. I will definitely stay here in number 7. Don’t judge a book by its cover as the outside is definitely an older cottage."
United States
Elaine E.
$143 nightly
The price is $153
Sep 9 - Sep 10
Total with taxes and fees
Walk to Lake & Strip | Firepit & Grill
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

Best Western Plus Mentor-Cleveland Northeast

Best Western Plus Mentor-Cleveland Northeast

10/10 Excellent
"From check-in to checkout, it checked all of our boxes. Easy to find from i80. Quiet and safe neighborhood. Ample parking. Room was clean. Breakfast was great."
natalie 1-night trip
Posted 23 hours ago
Best Western Plus Mentor-Cleveland Northeast

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 $127 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?

Lakefront home just minutes from wineries. Backyard sunsets!: This vacation home rental outside of Windsor offers a garden, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so 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 Punderson Lake. Windsor Mills Covered Bridge and Huntsburg Town Hall 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.