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

Holiday Homes in Windsor

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Windsor holiday homes

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, (98 reviews)
"Great location to enjoy some peaceful country living!"
United States
Jerry L.
The price is AU$322
includes taxes & fees
27 Sept - 28 Sept
Little house on the farm
A living room with a brown leather sofa, two armchairs, a small table with a lamp, and a striped rug.

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, (142 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$242
includes taxes & fees
27 Sept - 28 Sept
Conveniently located 2 bedroom home only minutes from hiking and state park fun!
A bedroom with a bed, a ceiling fan, a TV on a dresser, and two windows with blinds.

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, (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
The price is AU$273
includes taxes & fees
27 Sept - 28 Sept
A great stay, close to Spire, GOTL, & Wineries....King Bed!
A square fire pit table with two metal chairs on a wooden deck.

4. 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.
The price is AU$243
includes taxes & fees
9 Oct - 10 Oct
Beautiful cabin situated on wooded land with nice yard clearing and small stream
A living room with a brown sofa, a coffee table, a TV, and a ceiling fan.

5. 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, (22 reviews)
"Good stay"
Canada
Corey
The price is AU$294
includes taxes & fees
27 Sept - 28 Sept
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
A cabin with a deck, two lounge chairs, and a small table.

6. 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$325
includes taxes & fees
29 Sept - 30 Sept
Tiny Haven

7. 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, (58 reviews)
"Great location. Walkable to town. Very clean home and very comfortable. Great backyard and front and back decks. Great amenities"
United States
Susanne
The price is AU$345
includes taxes & fees
20 Oct - 21 Oct
Spacious 2bed on a Private 1 acre Lot by Lake, Sleeps 8--Walk to Strip & Golf
A modern kitchen with white cabinets, a stainless steel microwave, a gas stove, and a tiled backsplash.

8. GOTL Coastal Cottage- Sunset Vacation Rentals

GOTL Coastal Cottage- Sunset Vacation Rentals
Geneva
9.0 out of 10, Wonderful, (86 reviews)
"location"
United States
Donna T.
The price is AU$356
includes taxes & fees
27 Sept - 28 Sept
GOTL Coastal Cottage- Sunset Vacation Rentals
Two chairs with antler backs and a table in front of a wooden wall.

9. Highland House | Wine Country | Private Hot Tub

Highland House | Wine Country | Private Hot Tub
Madison
The price is AU$584
includes taxes & fees
28 Sept - 29 Sept
Highland House | Wine Country | Private Hot Tub
A garden with a wooden arbor and various plants, a green shed in the background, and a gravel path.

10. 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$757
includes taxes & fees
28 Sept - 29 Sept
The Thistle House off Chardon Square
A modern outdoor deck with seating and a glass enclosure, surrounded by lush greenery and trees.

11. Lakeside Chalet | Private Lake | Hot Tub | Views

Lakeside Chalet | Private Lake | Hot Tub | Views
Madison
The price is AU$789
includes taxes & fees
1 Oct - 2 Oct
Lakeside Chalet | Private Lake | Hot Tub | Views
A compact room with a blue sofa, a wooden bench, a small table, and a white chair. A lamp is on the floor, and a door leads to a bathroom with a sink and a mirror.

12. King Bed With Living Room - NKS

King Bed With Living Room - NKS
Geneva
9.0 out of 10, Wonderful, (6 reviews)
"Had a wonderful one night stay. Will definitely stay again. Everything was so clean, updated and comfortable. The location is fantastic for walking the strip."
United States
Robin S.
The price is AU$190
includes taxes & fees
25 Oct - 26 Oct
King Bed With Living Room - NKS
A modern kitchen with a refrigerator, two bar stools, and a dining area with a table and chairs.

13. 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
9.2 out of 10, Wonderful, (21 reviews)
"Was very cozy, quiet and well kept. Would stay there again."
United States
Christopher
The price is AU$320
includes taxes & fees
25 Sept - 26 Sept
Charming 2-bedroom Suite with balcony overlooking the Lake in Fairport Harbor
A house with a white picket fence, a red door, and a brick pathway leading to the entrance.

14. Farmhouse of Stoneycreek Acres, our Family Farm

Farmhouse of Stoneycreek Acres, our Family Farm
Newbury
9.8 out of 10, Exceptional, (22 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$718
includes taxes & fees
28 Sept - 29 Sept
Farmhouse of Stoneycreek Acres, our Family Farm
A living room with a dark grey sofa, white armchair, and a coffee table with a vase of flowers. There are three framed artworks above the sofa and a plant on the side.

15. Stylish 4 Bedroom Home in Geneva, Ohio. Near Wineries, SPIRE Institute, GOTL

Stylish 4 Bedroom Home in Geneva, Ohio. Near Wineries, SPIRE Institute, GOTL
Geneva
10.0 out of 10, Exceptional, (17 reviews)
"Great place and close to lots of places and activities."
United States
Lawrence F.
Stylish 4 Bedroom Home in Geneva, Ohio. Near Wineries, SPIRE Institute, GOTL
A coastal landscape with a rocky shoreline and grassy foreground.

16. House 1 mile from Geneva on Lake. We have several wineries in the area.

House 1 mile from Geneva on Lake. We have several wineries in the area.
Geneva
9.6 out of 10, Exceptional, (45 reviews)
"Roomy house in an accessible location! Grwt place to stay with our dogs with easy, drivable access to both Geneva and the Geneva-on-the-lake strip. Had a great weekend and host was very friendly and communicative. Large fenced in backyard was a great bonus."
United States
Sara W.
The price is AU$650
includes taxes & fees
24 Oct - 25 Oct
House 1 mile from Geneva on Lake. We have several wineries in the area.
A modern kitchen with white cabinets, a wooden countertop, and a dining area with a table and chairs.

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

Lovely private 3 bedroom house nestled in the Hiram countryside.
Garrettsville
9.2 out of 10, Wonderful, (15 reviews)
"Beautiful home, very clean"
United States
Kara A.
The price is AU$482
includes taxes & fees
27 Sept - 28 Sept
Lovely private 3 bedroom house nestled in the Hiram countryside.
A hallway with a white wall, a wooden floor, a white counter, and a chandelier.

18. Willow Woods Retreat - Farmhouse - Patio & Nature

Willow Woods Retreat - Farmhouse - Patio & Nature
Kirtland
9.2 out of 10, Wonderful, (42 reviews)
"We enjoyed our stay and the accommodations were as expected."
United States
Cherylee L.
The price is AU$407
includes taxes & fees
4 Oct - 5 Oct
Willow Woods Retreat - Farmhouse - Patio & Nature
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

19. Wine Country Escape - Hot Tub - Sleeps 12

Wine Country Escape - Hot Tub - Sleeps 12
Geneva
10.0 out of 10, Exceptional, (15 reviews)
"Our house was great! We did have some ants in the kitchen but that problem was addressed quickly. We would stay here again!"
United States
Melissa
The price is AU$930
includes taxes & fees
8 Oct - 9 Oct
Wine Country Escape - Hot Tub - Sleeps 12
A balcony with a view of the sea, a pier, beach chairs, and a rocky shoreline.

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, (61 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.
The price is AU$378
includes taxes & fees
6 Oct - 7 Oct
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.
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Top Windsor Hotel Reviews

Comfort Inn Painesville - Concord

Comfort Inn Painesville - Concord

10/10 Excellent
"We enjoyed our stay and plan on staying at this hotel again. It was very clean and updated."
Michael P 1-night trip
Posted 1 hour ago
Comfort Inn Painesville - Concord

Find out more about Windsor

Windsor Holiday Homes information

Number of reviews
514
Accommodation
185 Holiday Homes
Lowest Price
AU$190
Highest Price
AU$930

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