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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Windsor holiday rentals

A two-story house with a front porch, a small garden, and a wooden deck.

1. Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (100 reviews)
"Great location to enjoy some peaceful country living!"
United States
Jerry L.
The price is AU$319
includes taxes & fees
27 Oct - 28 Oct
Little house on the farm
A covered porch with wicker chairs and a blue patterned rug.

2. 2 bedroom apartment in the beautiful Middlefield countryside!

2 bedroom apartment in the beautiful Middlefield countryside!
Middlefield
8.6 out of 10, Excellent, (7 reviews)
"Fantastic clean and easy perfect for our quick trip!"
United States
Ashley B.
The price is AU$269
includes taxes & fees
3 Nov - 4 Nov
2 bedroom apartment in the beautiful Middlefield countryside!
A rustic kitchen with wooden beams, a central island, bar stools, and a dining table with placemats.

3. 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, (62 reviews)
"Folks this cabin is amazing! Rustic in design, modern in amenities and so very comfortable. Exceptional detail was paid to decor and quality furnishings which round out one of the nicest VRBO I've stayed at."
United States
Amy P.
The price is AU$336
includes taxes & fees
3 Nov - 4 Nov
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
A staircase leading to a kitchen with dark wooden cabinets and a stainless steel refrigerator.

4. Nestled Inn Mespo Modern & Cozy Apartment

Nestled Inn Mespo Modern & Cozy Apartment
Middlefield
10.0 out of 10, Exceptional, (11 reviews)
"Very nice people. Everything is very fresh, new and very well decorated."
United States
Kelly G.
The price is AU$322
includes taxes & fees
5 Nov - 6 Nov
Nestled Inn Mespo Modern & Cozy Apartment
A wooden two-story building with a balcony, a front door, and a sign that says "OPEN".

5. 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, (72 reviews)
"Really nice place to stay."
United States
Phillip
The price is AU$233
includes taxes & fees
27 Oct - 28 Oct
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
A living room with a brown leather sofa, two armchairs, a small table with a lamp, and a striped rug.

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, (142 reviews)
"The house was perfect for our stay and was exactly as described!"
United States
Michael R.
The price is AU$244
includes taxes & fees
26 Oct - 27 Oct
Conveniently located 2 bedroom home only minutes from hiking and state park fun!
A square fire pit table with two metal chairs on a wooden deck.

7. 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
9.8 out of 10, Exceptional, (14 reviews)
"Wonderful stay :) "
United States
Jennifer S.
The price is AU$244
includes taxes & fees
6 Nov - 7 Nov
Beautiful cabin situated on wooded land with nice yard clearing and small stream
A cabin with a metal exterior, a sign indicating 'Cabin No. 2', and a paved driveway leading to it.

8. 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
The price is AU$351
includes taxes & fees
2 Nov - 3 Nov
Romantic Woodside Cabin | Hot Tub & Fire Pit
A bedroom with a bed, a ceiling fan, a TV on a dresser, and two windows with blinds.

9. 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, (49 reviews)
"The house was clean, well furnished, and comfortable. Anthony was in contact and available if needed. We enjoyed our visit very much."
United States
Nancy M.
The price is AU$286
includes taxes & fees
29 Oct - 30 Oct
A great stay, close to Spire, GOTL, & Wineries....King Bed!
A cabin with a deck, two lounge chairs, and a small table.

10. Tiny Haven

Tiny Haven
Kinsman
10.0 out of 10, Exceptional, (33 reviews)
"Absolutely a lovely place to stay! Felt like home from the minute we walked in the door. The owners amazing cookies are to die for!!! Would love to go back and stay again!"
United States
Amy M.
The price is AU$323
includes taxes & fees
27 Oct - 28 Oct
Tiny Haven
A living room with a brown sofa, a coffee table, a TV, and a ceiling fan.

11. 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, (24 reviews)
"Good stay"
Canada
Corey
The price is AU$294
includes taxes & fees
1 Nov - 2 Nov
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
A living room with a flat-screen TV mounted on the wall, a dark wood fireplace, and a brown leather sofa.

12. Quaint recently renovated apartment with AC in Geneva close to lake and wineries

Quaint recently renovated apartment with AC in Geneva close to lake and wineries
Geneva
9.8 out of 10, Exceptional, (7 reviews)
"For a last minute stay for a big event, it was just what we need it. It was a little small but it had everything we would have wanted for the price."
United States
Donna G.
The price is AU$280
includes taxes & fees
27 Oct - 28 Oct
Quaint recently renovated apartment with AC in Geneva close to lake and wineries
A covered outdoor deck with a black wicker sofa, a small table, and a chair.

13. On The Strip • Cozy GOTL Vacation Cottage

On The Strip • Cozy GOTL Vacation Cottage
Geneva
9.4 out of 10, Exceptional, (111 reviews)
"Very pleasant stay"
United States
Daniel M.
The price is AU$367
includes taxes & fees
4 Nov - 5 Nov
On The Strip • Cozy GOTL Vacation Cottage
A wooden deck with two metal chairs and a small round table.

14. 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.
The price is AU$395
includes taxes & fees
5 Nov - 6 Nov
Cozy Country Apartment in Heart of Geauga County
A modern kitchen with a wooden countertop, stainless steel sink, and a black refrigerator.

15. 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
The price is AU$271
includes taxes & fees
20 Nov - 21 Nov
Peaceful private apartment in the charming Hiram countryside
A garden with a wooden arbor and various plants, a green shed in the background, and a gravel path.

16. The Thistle House off Chardon Square

The Thistle House off Chardon Square
Chardon
10.0 out of 10, Exceptional, (48 reviews)
"Totally charming, great kitchen. Excellent access to all that Chardon has to offer. We were there only a short time but the beach was stupendous. Felt welcoming and historic . . . Would recommend."
United States
Pamela
The price is AU$740
includes taxes & fees
28 Oct - 29 Oct
The Thistle House off Chardon Square
A small cabin with a porch, two Adirondack chairs, a round table, and a screened-in area.

17. Cabin 1 The Sunrise Patio

Cabin 1 The Sunrise Patio
Geneva
9.4 out of 10, Exceptional, (18 reviews)
"Host was amazing"
United States
Kim C.
The price is AU$244
includes taxes & fees
7 Nov - 8 Nov
Cabin 1 The Sunrise Patio
A small house with solar panels, a porch with outdoor furniture, and a wooden deck.

18. Cozy Shed-Teau in Geneva + Firepit

Cozy Shed-Teau in Geneva + Firepit
Geneva
9.6 out of 10, Exceptional, (14 reviews)
"Very nice property"
United States
William M B.
The price is AU$207
includes taxes & fees
4 Nov - 5 Nov
Cozy Shed-Teau in Geneva + Firepit
A modern kitchen with a central island, bar stools, a window with a view, and a 'DINE' sign on the wall.

19. Country Cottage Farm Stay at Stoneycreek Acres

Country Cottage Farm Stay at Stoneycreek Acres
Newbury
10.0 out of 10, Exceptional, (76 reviews)
"Molly and Dave were so friendly and ready to help us with whatever we needed. We felt so welcomed and the cottage was very clean and cozy. It was a great place to come back to and relax. The farm animals were so fun to see out our back windows and as we walked around the property. Will definitely be keeping this on our list to come back too."
United States
Allison M.
The price is AU$520
includes taxes & fees
2 Nov - 3 Nov
Country Cottage Farm Stay at Stoneycreek Acres
A compact living space with a kitchenette, a dining area with bar stools, a television, and a ceiling fan.

20. The Riesling Cottage - GOTL Strip - Cozy & Quaint

The Riesling Cottage - GOTL Strip - Cozy & Quaint
Geneva
10.0 out of 10, Exceptional, (27 reviews)
"Loved it!! I’ll definitely stay here again! "
United States
Rebecca S.
The price is AU$312
includes taxes & fees
25 Oct - 26 Oct
The Riesling Cottage - GOTL Strip - Cozy & Quaint
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
"Was a most enjoyable place to stay. Clean, wonderful rooms, quiet. Everything looked nice and welcoming. Appreciate a room where the heating/cooling unit is quiet as this one was. Also the bath exhaust fan was so quiet, almost unnoticeable. Wonderful! The breakfast was hot and enjoyable as well. TV channel listing was provided in the room. The perfect place to stay. Would highly recommend. Room was perfect and smelled clean. Thank you for a wonderful stay."
David R 1-night trip
Posted 11 hours ago
Best Western Plus Mentor-Cleveland Northeast

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Windsor holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as AU$104 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday 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 holiday.

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. 

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?

Center Strip | Pets OK | Wi-Fi | Near Wineries: This holiday home rental outside of Windsor is located on a lake, and offers a BBQ, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

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 Middlefield Village Center 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.