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

Windsor Vacation Rentals

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

Our top choices for Windsor vacation 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 CA $218
CA $316 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $127
CA $240 total
includes taxes & fees
Sep 27 - Sep 28
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 CA $126
CA $267 total
includes taxes & fees
Sep 27 - Sep 28
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 CA $183
CA $238 total
includes taxes & fees
Oct 9 - Oct 10
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 CA $138
CA $291 total
includes taxes & fees
Sep 27 - Sep 28
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 CA $176
CA $319 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $120
CA $335 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $168
CA $358 total
includes taxes & fees
Sep 27 - Sep 28
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 CA $485
CA $588 total
includes taxes & fees
Sep 28 - Sep 29
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 CA $472
CA $754 total
includes taxes & fees
Sep 28 - Sep 29
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 CA $647
CA $784 total
includes taxes & fees
Oct 1 - Oct 2
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 CA $140
CA $186 total
includes taxes & fees
Sep 27 - Sep 28
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 CA $212
CA $312 total
includes taxes & fees
Sep 25 - Sep 26
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 CA $443
CA $723 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $458
CA $658 total
includes taxes & fees
Sep 27 - Sep 28
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 CA $261
CA $494 total
includes taxes & fees
Sep 27 - Sep 28
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 CA $154
CA $410 total
includes taxes & fees
Oct 4 - Oct 5
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 CA $293
CA $842 total
includes taxes & fees
Oct 5 - Oct 6
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 CA $232
CA $377 total
includes taxes & fees
Oct 18 - Oct 19
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

Wingate by Wyndham Geneva at SPIRE Academy

Wingate by Wyndham Geneva at SPIRE Academy

10/10 Excellent
"Everything was newly renovated. The bed and pillows were amazing ! As with most hotels there's a lot of blank wall space. I would love to see some hooks to hang a purse or bag. But everything was fantastic !"
Andy 1-night trip
Posted 3 hours ago
Wingate by Wyndham Geneva at SPIRE Academy

Find out more about Windsor

Windsor Vacation Homes information

Number of reviews
514
Accommodation
186 Vacation Homes
Lowest Price
CA $186
Highest Price
CA $842

Explore a world of travel with Expedia