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

Windsor Holiday 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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (99 reviews)
"Great location to enjoy some peaceful country living!"
United States
Jerry L.
The price is NZ$402
includes taxes & fees
6 Oct - 7 Oct
Little house on the farm
A rustic kitchen with wooden beams, a central island, bar stools, and a dining table with placemats.

2. 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, (58 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 NZ$415
includes taxes & fees
6 Oct - 7 Oct
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.

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 NZ$402
includes taxes & fees
6 Oct - 7 Oct
Nestled Inn Mespo Modern & Cozy Apartment
A covered porch with wicker chairs and a blue patterned rug.

4. 2 bedroom apartment in the beautiful Middlefield countryside!

2 bedroom apartment in the beautiful Middlefield countryside!
Middlefield
8.4 out of 10, Very good, (6 reviews)
"Fantastic clean and easy perfect for our quick trip!"
United States
Ashley B.
The price is NZ$331
includes taxes & fees
6 Oct - 7 Oct
2 bedroom apartment in the beautiful Middlefield countryside!
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, (71 reviews)
"Really nice place to stay."
United States
Phillip
The price is NZ$284
includes taxes & fees
6 Oct - 7 Oct
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
A bedroom with a wooden ceiling, a bed with a wooden headboard, a blue chair, a bench, and a cowhide rug.

6. 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 NZ$490
includes taxes & fees
6 Oct - 7 Oct
Romantic Woodside Cabin | Hot Tub & Fire Pit
A living room with a brown leather sofa, two armchairs, a small table with a lamp, and a striped rug.

7. 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 NZ$303
includes taxes & fees
6 Oct - 7 Oct
Conveniently located 2 bedroom home only minutes from hiking and state park fun!
A garden with a wooden arbor and various plants, a green shed in the background, and a gravel path.

8. 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 NZ$946
includes taxes & fees
6 Oct - 7 Oct
The Thistle House off Chardon Square
A modern kitchen with a central island, bar stools, a window with a view, and a 'DINE' sign on the wall.

9. Country Cottage Farm Stay at Stoneycreek Acres

Country Cottage Farm Stay at Stoneycreek Acres
Newbury
10.0 out of 10, Exceptional, (76 reviews)
"Excellent communication with host and extremely clean, peaceful and beautiful place to stay "
United States
Jennifer T.
The price is NZ$662
includes taxes & fees
2 Nov - 3 Nov
Country Cottage Farm Stay at Stoneycreek Acres
A house with a white picket fence, a red door, and a brick pathway leading to the entrance.

10. 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 NZ$906
includes taxes & fees
6 Oct - 7 Oct
Farmhouse of Stoneycreek Acres, our Family Farm
A spacious log cabin interior with a dining area, living room, fireplace, and a balcony.

11. Hot Tub - Luxury 3BR Authentic Log Cabin Retreat Near Wineries, GOTL & Spire.

Hot Tub - Luxury 3BR Authentic Log Cabin Retreat Near Wineries, GOTL & Spire.
Geneva
10.0 out of 10, Exceptional, (21 reviews)
"Great Stay. "
United States
Sam K.
The price is NZ$707
includes taxes & fees
2 Nov - 3 Nov
Hot Tub - Luxury 3BR Authentic Log Cabin Retreat Near Wineries, GOTL & Spire.
A compact kitchen with a sink, stove, microwave, and cabinets.

12. 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, (6 reviews)
The price is NZ$223
includes taxes & fees
6 Oct - 7 Oct
Cozy 1-bedroom Camper on the lake with AC in adorable Cortland.
A small, single-story house with a gabled roof, surrounded by a forest.

13. Storybook Cottage in the Woods

Storybook Cottage in the Woods
Geneva
10.0 out of 10, Exceptional, (4 reviews)
"We stayed here for my wedding and it was a great little cabin. Perfect location for where we needed to be with everything convenient nearby. The host was excellent, he had great communication and the check-in process was easy. The place itself was super cute and I would totally stay there again or recommend it to anyone!"
United States
Zoe N.
Storybook Cottage in the Woods
A cabin with a deck, two lounge chairs, and a small table.

14. 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 NZ$402
includes taxes & fees
7 Oct - 8 Oct
Tiny Haven
A log cabin with a porch and a small deck, surrounded by a forest.

15. Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.

Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.
Burton
10.0 out of 10, Exceptional, (9 reviews)
"My friends and I had a great stay at the cabins in newberry axel is very kind and the property is very nice"
United States
David H.
The price is NZ$454
includes taxes & fees
6 Oct - 7 Oct
Camp Newbury: 100% off grid. 2 log cabins, pavilion, trails and shooting range.
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 NZ$493
includes taxes & fees
6 Oct - 7 Oct
Cozy Country Apartment in Heart of Geauga County
A bedroom with a bed, a ceiling fan, a TV on a dresser, and two windows with blinds.

17. 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 NZ$352
includes taxes & fees
6 Oct - 7 Oct
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.

18. 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, (23 reviews)
"Good stay"
Canada
Corey
The price is NZ$362
includes taxes & fees
6 Oct - 7 Oct
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.

19. 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, (6 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 NZ$344
includes taxes & fees
6 Oct - 7 Oct
Quaint recently renovated apartment with AC in Geneva close to lake and wineries
A modern living room with a staircase, a sofa set, and a coffee table.

20. Small town vibes in Garrettsville

Small town vibes in Garrettsville
Garrettsville
10.0 out of 10, Exceptional, (5 reviews)
"Great host"
United States
Richard B.
The price is NZ$863
includes taxes & fees
6 Oct - 7 Oct
Small town vibes in Garrettsville
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

8/10 Good
"Our first room had dirty bed sheets. We had to request to move to a new room with clean sheets."
Jen 1-night trip
Posted 1 hour ago
Wingate by Wyndham Geneva at SPIRE Academy

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 favorite 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 depends 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 NZ$264 per night. Entering your travel dates in the search wizard you might find 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.