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

Holiday Homes in Windsor

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Windsor holiday homes

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 AU$320
includes taxes & fees
13 Aug - 14 Aug
Little house on the farm
Smart TV, fireplace

2. 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 AU$267
includes taxes & fees
11 Aug - 12 Aug
Conveniently located 2 bedroom home only minutes from hiking and state park fun!
2 bedrooms, free WiFi, bed sheets

3. 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, (44 reviews)
"Very clean.. spacious, Close to wineries."
United States
frances f.
The price is AU$295
includes taxes & fees
11 Aug - 12 Aug
A great stay, close to Spire, GOTL, & Wineries....King Bed!
Living area

4. 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 AU$300
includes taxes & fees
11 Aug - 12 Aug
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
Terrace/patio

5. Tiny Haven

Tiny Haven
Kinsman
10.0 out of 10, Exceptional, (32 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 AU$320
includes taxes & fees
11 Aug - 12 Aug
Tiny Haven
Interior

6. KC's Hideout your true Western retreat in the heart of Amish Country!

KC's Hideout your true Western retreat in the heart of Amish Country!
Middlefield
10.0 out of 10, Exceptional, (1 review)
"Loved this property! The hosts were wonderful and thought of the little extras that many don’t. Everything was clean and decorated beautifully, plus there was ample parking and even a large garage which my truck fit in perfectly. I brought along a horse and trailer, which they also accommodated and parking for large rigs is a huge plus. My horse had a nice sized stall with sawdust and was also provided with a large turnout, which she loved. Coffee, snacks and toiletries were provided and they...
United States
Rebecca R.
The price is AU$495
includes taxes & fees
6 Sept - 7 Sept
KC's Hideout your true Western retreat in the heart of Amish Country!
Interior

7. Willow Woods Retreat - Farmhouse - Patio & Nature

Willow Woods Retreat - Farmhouse - Patio & Nature
Kirtland
9.4 out of 10, Exceptional, (41 reviews)
"Very nice stay. "
United States
MichaelLarryBetty S.
The price is AU$446
includes taxes & fees
11 Aug - 12 Aug
Willow Woods Retreat - Farmhouse - Patio & Nature
Property grounds

8. 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)
"Was perfect for our short stay. "
United States
Jayne F.
The price is AU$261
includes taxes & fees
24 Aug - 25 Aug
Center Strip | Pets OK | Wi-Fi | Near Wineries
Interior

9. Lake Erie Retreat – Hidden Village Escape

Lake Erie Retreat – Hidden Village Escape
Perry
10.0 out of 10, Exceptional, (3 reviews)
"Everything was there that we needed it was a very nice home definitely stay again"
United States
Richard P.
The price is AU$531
includes taxes & fees
17 Aug - 18 Aug
Lake Erie Retreat – Hidden Village Escape
Property grounds

10. The Thistle House off Chardon Square

The Thistle House off Chardon Square
Chardon
10.0 out of 10, Exceptional, (47 reviews)
"This is a charming home and had everything we needed. It is very well appointed, comfortable and a wonderful place to return to."
United States
Brian
The price is AU$754
includes taxes & fees
11 Aug - 12 Aug
The Thistle House off Chardon Square
Coffee/tea maker, fridge, microwave, oven

11. Dog-Friendly Retreat Near Wineries/Spire/GOTL

Dog-Friendly Retreat Near Wineries/Spire/GOTL
Madison-on-the-Lake
9.4 out of 10, Exceptional, (36 reviews)
"We enjoyed our stay here. It was a great location for us with easy parking and easy access. The house was nice and really clean. We'd definitely come back!"
United States
Betsy R.
The price is AU$385
includes taxes & fees
8 Sept - 9 Sept
Dog-Friendly Retreat Near Wineries/Spire/GOTL
Terrace/patio

12. On The Strip • Cozy GOTL Vacation Cottage

On The Strip • Cozy GOTL Vacation Cottage
Geneva
9.4 out of 10, Exceptional, (106 reviews)
"Perfect location, clean house!"
United States
Michelle S.
The price is AU$403
includes taxes & fees
13 Aug - 14 Aug
On The Strip • Cozy GOTL Vacation Cottage
Private kitchen

13. Lovely private 3 bedroom house nestled in the Hiram countryside.

Lovely private 3 bedroom house nestled in the Hiram countryside.
Garrettsville
9.0 out of 10, Wonderful, (12 reviews)
"Beautiful home, very clean"
United States
Kara A.
The price is AU$485
includes taxes & fees
13 Aug - 14 Aug
Lovely private 3 bedroom house nestled in the Hiram countryside.
Interior

14. Charming 2-bedroom Suite with balcony overlooking the Lake in Fairport Harbor

Charming 2-bedroom Suite with balcony overlooking the Lake in Fairport Harbor
Fairport Harbor
9.6 out of 10, Exceptional, (17 reviews)
"Was very cozy, quiet and well kept. Would stay there again."
United States
Christopher
The price is AU$318
includes taxes & fees
9 Sept - 10 Sept
Charming 2-bedroom Suite with balcony overlooking the Lake in Fairport Harbor
Smart TV, offices

15. Small town vibes in Garrettsville

Small town vibes in Garrettsville
Garrettsville
10.0 out of 10, Exceptional, (5 reviews)
"Very clean, solid rental. "
United States
Christopher P.
The price is AU$689
includes taxes & fees
11 Aug - 12 Aug
Small town vibes in Garrettsville
Exterior detail

16. Farmhouse of Stoneycreek Acres, our Family Farm

Farmhouse of Stoneycreek Acres, our Family Farm
Newbury
9.8 out of 10, Exceptional, (21 reviews)
"We had a great time at our stay! The house was so cute and cozy, it had everything we needed stocked, and the owner was so friendly through the whole process. Would absolutely stay here again!"
United States
Madison S.
The price is AU$730
includes taxes & fees
11 Aug - 12 Aug
Farmhouse of Stoneycreek Acres, our Family Farm
Property grounds

17. Strip Location | Pet Friendly | Fire Pit

Strip Location | Pet Friendly | Fire Pit
Geneva
9.6 out of 10, Exceptional, (246 reviews)
"Had a lovely stay. "
United States
Tammy
The price is AU$481
includes taxes & fees
18 Aug - 19 Aug
Strip Location | Pet Friendly | Fire Pit
1 bedroom, free WiFi, bed sheets

18. Quaint cottage a short walk from the GTOL strip!

Quaint cottage a short walk from the GTOL strip!
Geneva-on-the-Lake
9.8 out of 10, Exceptional, (86 reviews)
"We really enjoyed our stay. The home was beautiful and cozy. We also very much appreciated the water left for guest. Also, we loved how close it was to the strip."
United States
Tiffany M.
The price is AU$298
includes taxes & fees
19 Aug - 20 Aug
Quaint cottage a short walk from the GTOL strip!
Smart TV

19. Spacious 2bed on a Private 1 acre Lot by Lake, Sleeps 8--Walk to Strip & Golf

Spacious 2bed on a Private 1 acre Lot by Lake, Sleeps 8--Walk to Strip & Golf
Geneva
9.0 out of 10, Wonderful, (55 reviews)
"The rooms were very clean. Kitchen had everything you need. Quiet area."
United States
Christian D.
The price is AU$399
includes taxes & fees
12 Aug - 13 Aug
Spacious 2bed on a Private 1 acre Lot by Lake, Sleeps 8--Walk to Strip & Golf
Property grounds

20. Lakefront condo --2BR/2Bath Sleeps 4 Private beach and lake front balcony

Lakefront condo --2BR/2Bath Sleeps 4 Private beach and lake front balcony
Geneva
9.8 out of 10, Exceptional, (60 reviews)
"This property is one of the nicest we have stayed at. Everything was clean, we had everything we needed, and had the most enjoyable weekend! We will absolutely stay here again! "
United States
Jen A.
Lakefront condo --2BR/2Bath Sleeps 4 Private beach and lake front balcony
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windsor Hotel Reviews

The Lodge at Geneva-on-the-Lake

The Lodge at Geneva-on-the-Lake

10/10 Excellent
"Family friendly."
Diego 1-night trip
Posted 3 hours ago
The Lodge at Geneva-on-the-Lake

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
1,314
Accommodation
185 Holiday Homes
Lowest Price
AU$261
Highest Price
AU$754

Explore a world of travel with Expedia