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

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.
The price is AED 569
AED 841 total
includes taxes & fees
7 Aug - 8 Aug
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.
The price is AED 477
AED 789 total
includes taxes & fees
25 Aug - 26 Aug
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.
The price is AED 551
AED 757 total
includes taxes & fees
7 Aug - 8 Aug
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
The price is AED 393
AED 595 total
includes taxes & fees
11 Aug - 12 Aug
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.
The price is AED 459
AED 841 total
includes taxes & fees
10 Aug - 11 Aug
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
The price is AED 380
AED 689 total
includes taxes & fees
10 Aug - 11 Aug
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.
The price is AED 367
AED 466 total
includes taxes & fees
10 Aug - 11 Aug
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.
The price is AED 729
AED 835 total
includes taxes & fees
11 Aug - 12 Aug
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
The price is AED 360
AED 772 total
includes taxes & fees
9 Aug - 10 Aug
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.
The price is AED 370
AED 756 total
includes taxes & fees
9 Aug - 10 Aug
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.
The price is AED 423
AED 514 total
includes taxes & fees
10 Aug - 11 Aug
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, (12 reviews)
"Every detail was thought of, from the comfortable bedding to the well-appointed outdoor area."
United States
Stephen S.
The price is AED 404
AED 525 total
includes taxes & fees
10 Aug - 11 Aug
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
The price is AED 413
AED 503 total
includes taxes & fees
10 Aug - 11 Aug
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
The price is AED 729
AED 835 total
includes taxes & fees
13 Aug - 14 Aug
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.
The price is AED 459
AED 569 total
includes taxes & fees
9 Aug - 10 Aug
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, (227 reviews)
"We thought it was perfect for what we needed 2 dogs And a nice park around corner Perfect place!!"
United States
Scott
The price is AED 363
AED 1,005 total
includes taxes & fees
11 Aug - 12 Aug
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
The price is AED 279
AED 1,076 total
includes taxes & fees
26 Aug - 27 Aug
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
The price is AED 331
AED 697 total
includes taxes & fees
10 Aug - 11 Aug
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
The price is AED 241
AED 678 total
includes taxes & fees
24 Aug - 25 Aug
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.
The price is AED 482
AED 979 total
includes taxes & fees
10 Aug - 11 Aug
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

Americas Best Value Inn Austinburg

Americas Best Value Inn Austinburg

10/10 Excellent
"Jamie is a welcoming, friendly, and helpful hotel manager! She absolutely made us feel welcome! The rooms were clean, except the carpets could probably use a cleaning. Very little trash outside the building, but it appears that someone is cleaning it up daily. Super convenient location!"
David 6-night trip
Posted 9 hours ago
Americas Best Value Inn Austinburg

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.