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 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Windsor vacation 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, (99 reviews)
"Great location to enjoy some peaceful country living!"
United States
Jerry L.
The price is ￥24,538
￥36,253 total
includes taxes & fees
Oct 13 - Oct 14
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 ￥15,831
￥29,604 total
includes taxes & fees
Oct 20 - Oct 21
2 bedroom apartment in the beautiful Middlefield countryside!
A staircase leading to a kitchen with dark wooden cabinets and a stainless steel refrigerator.

3. Nestled Inn Mespo Modern & Cozy Apartment

Nestled Inn Mespo Modern & Cozy Apartment
Middlefield
10.0 out of 10, Exceptional, (11 reviews)
"Beautiful place and very well taken care of."
United States
Andrew G.
The price is ￥26,913
￥36,253 total
includes taxes & fees
Oct 17 - Oct 18
Nestled Inn Mespo Modern & Cozy Apartment
A rustic kitchen with wooden beams, a central island, bar stools, and a dining table with placemats.

4. 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, (60 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 ￥23,430
￥37,360 total
includes taxes & fees
Oct 13 - Oct 14
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
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 ￥16,670
￥25,377 total
includes taxes & fees
Oct 13 - Oct 14
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 ￥14,248
￥27,229 total
includes taxes & fees
Oct 13 - Oct 14
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 ￥20,580
￥26,738 total
includes taxes & fees
Oct 30 - Oct 31
Beautiful cabin situated on wooded land with nice yard clearing and small stream
A compact kitchen with a sink, stove, microwave, and cabinets.

8. Cozy 1-bedroom Camper on the lake with AC in adorable Cortland.

Cozy 1-bedroom Camper on the lake with AC in adorable Cortland.
Cortland
9.8 out of 10, Exceptional, (7 reviews)
The price is ￥8,834
￥21,326 total
includes taxes & fees
Oct 13 - Oct 14
Cozy 1-bedroom Camper on the lake with AC in adorable Cortland.
A bedroom with a wooden ceiling, a bed with a wooden headboard, a blue chair, a bench, and a cowhide rug.

9. 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 ￥30,768
￥38,812 total
includes taxes & fees
Oct 21 - Oct 22
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.

10. 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, (47 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 ￥14,960
￥31,424 total
includes taxes & fees
Oct 18 - Oct 19
A great stay, close to Spire, GOTL, & Wineries....King Bed!
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 ￥14,960
￥32,532 total
includes taxes & fees
Oct 13 - Oct 14
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
A cabin with a deck, two lounge chairs, and a small table.

12. 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 ￥19,789
￥36,253 total
includes taxes & fees
Oct 13 - Oct 14
Tiny Haven
A modern kitchen with stainless steel appliances, white cabinetry, and a wooden countertop.

13. Recently updated apartment in a Triplex unit #1 close to wineries and the lake.

Recently updated apartment in a Triplex unit #1 close to wineries and the lake.
Geneva
9.6 out of 10, Exceptional, (44 reviews)
"Very nice place. Nice location. Would stay there again."
United States
Kelly B.
The price is ￥16,243
￥29,541 total
includes taxes & fees
Oct 13 - Oct 14
Recently updated apartment in a Triplex unit #1 close to wineries and the lake.
A living room with a flat-screen TV mounted on the wall, a dark wood fireplace, and a brown leather sofa.

14. 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 ￥17,240
￥30,780 total
includes taxes & fees
Oct 13 - Oct 14
Quaint recently renovated apartment with AC in Geneva close to lake and wineries
A compact kitchen with a microwave, stove, sink, and refrigerator.

15. Quaint Cozy 1-bedroom apartment in pleasant Geneva with AC, WiFi

Quaint Cozy 1-bedroom apartment in pleasant Geneva with AC, WiFi
Geneva
9.4 out of 10, Exceptional, (26 reviews)
"Super comfy bed, A/C was excellent, cute little 50’s style restaurant just down the road. "
United States
Stephanie
The price is ￥16,528
￥30,198 total
includes taxes & fees
Oct 13 - Oct 14
Quaint Cozy 1-bedroom apartment in pleasant Geneva with AC, WiFi
A wooden deck with two metal chairs and a small round table.

16. 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 ￥22,955
￥43,852 total
includes taxes & fees
Oct 13 - Oct 14
Cozy Country Apartment in Heart of Geauga County
A small house with solar panels, a porch with outdoor furniture, and a wooden deck.

17. 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 ￥15,958
￥21,182 total
includes taxes & fees
Oct 13 - Oct 14
Cozy Shed-Teau in Geneva + Firepit
A small cabin with a porch, two Adirondack chairs, a round table, and a screened-in area.

18. 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 ￥22,163
￥26,881 total
includes taxes & fees
Oct 13 - Oct 14
Cabin 1 The Sunrise Patio
A beach at sunset with waves crashing onto the shore.

19. LAKEFRONT LOFT-PERFECT COUPLES GETAWAY--rent 2 get 3rd free-until Oct. 30- ask!

LAKEFRONT LOFT-PERFECT COUPLES GETAWAY--rent 2 get 3rd free-until Oct. 30- ask!
Geneva
10.0 out of 10, Exceptional, (400 reviews)
"Great place to stay! Convenient location!"
United States
Debbie C.
The price is ￥16,623
￥23,494 total
includes taxes & fees
Oct 26 - Oct 27
LAKEFRONT LOFT-PERFECT COUPLES GETAWAY--rent 2 get 3rd free-until Oct. 30- ask!
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 ￥8,549
￥33,138 total
includes taxes & fees
Oct 13 - Oct 14
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.
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

Comfort Inn Painesville - Concord

Comfort Inn Painesville - Concord

8/10 Good
"Rooms are updated nicely. Breakfast was very good, they had pumpkin waffle batter and pumpkin spice coffee."
Julie Van 1-night trip
Posted 1 hour ago
Comfort Inn Painesville - Concord

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
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • 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 vacation rentals in Windsor?

Yes, we have vacation rentals near top local attractions in Windsor, or you can select a secluded option if you're looking for relaxation.

What are some of the best vacation home rentals in Windsor?

Center Strip | Pets OK | Wi-Fi | Near Wineries: This vacation home rental outside of Windsor is located on a lake and offers a barbecue grill, 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 larger area.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned accommodations you can reserve for a short or long stay in Windsor. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family getaway.