Windsor Holiday Rentals

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Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sept - 20 Sept

Our top choices for Windsor holiday rentals

Terrace/patio

Tiny Haven

Tiny Haven
Kinsman
10.0 out of 10, Exceptional, (27 reviews)
"This property is amazing! The hosts made our stay very pleasant with a clean, well appointed property. We definitely will be staying here again—hopefully soon!"
United States
Kathleen S.
The price is HK$980
HK$1,795 total
includes taxes & fees
1 Jun - 2 Jun
Tiny Haven
Property grounds

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

Center Strip Location|Pet Friendly|Wi-Fi|A/C|Steps from Winery & Golf Course
Geneva
9.4 out of 10, Exceptional, (234 reviews)
"Great location, clean & cozy!"
United States
Michele
Center Strip Location|Pet Friendly|Wi-Fi|A/C|Steps from Winery & Golf Course
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, (133 reviews)
"Great stay and pet friendly. Very clean and excellent, comfortable furniture. Definitely would stay again when in the area"
United States
Andrew B.
The price is HK$784
HK$1,426 total
includes taxes & fees
17 Jun - 18 Jun
Conveniently located 2 bedroom home only minutes from hiking and state park fun!
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, (38 reviews)
"Cabin was perfect for us. Nicely furnished and well kept. "
United States
William H.
The price is HK$980
HK$1,610 total
includes taxes & fees
1 Jun - 2 Jun
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
Fridge, microwave, oven, stovetop

Chardonnay Cottage - GOTL Strip - Cozy & Quaint

Chardonnay Cottage - GOTL Strip - Cozy & Quaint
Geneva
9.8 out of 10, Exceptional, (13 reviews)
"Clean cabin, with a great location. Host was quick to answer any questions we had. Would stay agian!"
United States
Aaron J.
The price is HK$423
HK$1,640 total
includes taxes & fees
1 Jun - 2 Jun
Chardonnay Cottage - GOTL Strip - Cozy & Quaint
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, (12 reviews)
"Loved this property. Was so clean and nice. "
United States
Allyson C.
The price is HK$769
HK$1,646 total
includes taxes & fees
1 Jun - 2 Jun
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
Combined shower/bathtub, towels, soap, toilet paper

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

Great Strip Location|WalktoLake|Wine Country|AC|Grill&Firepit|FamilyFriendly
Geneva
9.4 out of 10, Exceptional, (111 reviews)
"Omg there were wonderful fire pits (which we didn’t use for who knows why)? With a large stock of wood and excellent chairs. Easy in and out with luggage/gear, plenty of parking and all the amenities that you would need. Maybe take an extra throw/comforter? Truly on the strip ! The second bedroom has bunks but seem bigger than twin and the pullout couch was - well a pullout couch with the inner spring mattress"
United States
thomas
Great Strip Location|WalktoLake|Wine Country|AC|Grill&Firepit|FamilyFriendly
Exterior

Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (96 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$1,787 total
includes taxes & fees
1 Jun - 2 Jun
Little house on the 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$1,234
HK$2,357 total
includes taxes & fees
1 Jun - 2 Jun
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, (7 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
1 Jun - 2 Jun
Charming 1-bedroom cabin in Geneva
Property grounds

Pet Friendly | A/C | Wi-Fi & Cable | Grill |Walk to Lake| Firepit | Wine Country

Pet Friendly | A/C | Wi-Fi & Cable | Grill |Walk to Lake| Firepit | Wine Country
Geneva
9.6 out of 10, Exceptional, (214 reviews)
"Everything was clean and the kitchen was stocked to cook. The beds were comfortable and the bathroom was well supplied with everything you needed. I would definitely stay again.. "
United States
Matthew B.
Pet Friendly | A/C | Wi-Fi & Cable | Grill |Walk to Lake| Firepit | Wine Country
Private kitchen

Peaceful private apartment in the charming Hiram countryside

Peaceful private apartment in the charming Hiram countryside
Garrettsville
10.0 out of 10, Exceptional, (4 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$1,472 total
includes taxes & fees
1 Jun - 2 Jun
Peaceful private apartment in the charming Hiram countryside
Property grounds

Quiet tiny cabin near GOTL + fire pit

Quiet tiny cabin near GOTL + fire pit
Geneva
8.8 out of 10, Excellent, (3 reviews)
"Every detail was thought of, from the comfortable bedding to the well-appointed outdoor area."
United States
Stephen S.
The price is HK$853
HK$1,010 total
includes taxes & fees
1 Jun - 2 Jun
Quiet tiny cabin near GOTL + fire pit
Terrace/patio

Cabin 1 The Sunrise Patio

Cabin 1 The Sunrise Patio
Geneva
9.6 out of 10, Exceptional, (8 reviews)
"Teressa and her husband were amazing hosts! We enjoyed staying in a comfy quiet place! "
United States
danielle c.
The price is HK$1,019
HK$1,247 total
includes taxes & fees
11 Jun - 12 Jun
Cabin 1 The Sunrise Patio
Exterior

1 Bed 1 Bath Suite On Strip

1 Bed 1 Bath Suite On Strip
Geneva on the Lake
9.0 out of 10, Wonderful, (105 reviews)
"Place was very cozy and clean would highly recommend and we would stay there again when we come up!"
United States
Lois B.
The price is HK$628
HK$1,585 total
includes taxes & fees
7 Jun - 8 Jun
1 Bed 1 Bath Suite On Strip
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
9.8 out of 10, Exceptional, (40 reviews)
"Great stay"
United States
Freeman H.
The price is HK$980
HK$1,827 total
includes taxes & fees
7 Jun - 8 Jun
A great stay, close to Spire, GOTL, & Wineries....King Bed!
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$1,391
HK$1,579 total
includes taxes & fees
8 Jun - 9 Jun
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
Outdoor dining

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, (12 reviews)
"Wonderful stay :) "
United States
Jennifer S.
The price is HK$1,019
HK$1,324 total
includes taxes & fees
5 Jun - 6 Jun
Beautiful cabin situated on wooded land with nice yard clearing and small stream
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, (61 reviews)
"Great option for needing a place to stay while visiting family. "
United States
Katelin B.
The price is HK$748
HK$1,179 total
includes taxes & fees
8 Jun - 9 Jun
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
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

Hampton Inn & Suites Cleveland Mentor

Hampton Inn & Suites Cleveland Mentor

4/10 Poor
"We booked and paid for a suite room with a couch. They would not give us one even though that is what we booked and paid for. The front desk employees were not helpful or empathetic. When we arrived both the front desk employees were sitting outside on the side of the hotel and walked in just ahead of us. No other employees were there, so who was answering the phones, no one that’s who. Extremely unprofessional. We will not be staying here again. We only booked because they had suites and we didn’t get one or any kind of apology or compensation for the difference in the cost of the room! 😡"
Michelle 1-night trip
Posted 6 hours ago
Hampton Inn & Suites Cleveland Mentor

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:

  • View our selection of featured holiday rentals in Windsor
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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?

Lakefront Home Water Front Pet Friendly Steps from Winery Wi-Fi & Cable: This holiday home rental outside of Windsor is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, 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 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.