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

Windsor Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Windsor vacation rentals

Dining

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, (44 reviews)
"Wonderful place! We all want to go back for a longer stay - especially when it's warm enough to enjoy the screened in porch."
United States
Laura M.
$211 nightly
The price is $220
Jul 20 - Jul 21
Total with taxes and fees
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
Exterior

Little house on the farm

Little house on the farm
Middlefield
10.0 out of 10, Exceptional, (97 reviews)
"Absolutely perfect. Beautiful country home on a farm. Would 100% recommend and stay again. Amish store and restaurant just minutes away. Hosts left snacks and a variety of coffee and creamer choices. WiFi was great too as I had very little cell phone reception on the property. "
United States
Megan
$228 nightly
The price is $228
Jul 19 - Jul 20
Total with taxes and fees
Little house on the farm
Smart TV, fireplace

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, (137 reviews)
"Great stay and amazing host"
United States
Raven S.
$178 nightly
The price is $178
Jul 21 - Jul 22
Total with taxes and fees
Conveniently located 2 bedroom home only minutes from hiking and state park fun!
2 bedrooms, WiFi (free), bed sheets

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, (42 reviews)
"Great stay"
United States
Freeman H.
$203 nightly
The price is $203
Jul 19 - Jul 20
Total with taxes and fees
A great stay, close to Spire, GOTL, & Wineries....King Bed!
Living area

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, (15 reviews)
"Good stay"
Canada
Corey
$210 nightly
The price is $210
Jul 20 - Jul 21
Total with taxes and fees
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
Terrace/patio

Tiny Haven

Tiny Haven
Kinsman
10.0 out of 10, Exceptional, (30 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.
$229 nightly
The price is $229
Jul 19 - Jul 20
Total with taxes and fees
Tiny Haven
Terrace/patio

Cabin 1 The Sunrise Patio

Cabin 1 The Sunrise Patio
Geneva
9.0 out of 10, Wonderful, (13 reviews)
"Very easy, inconvenient check-in, a quiet and comfortable little area with plenty of options of things to do if you plan to stay for more than a few days. Also very accommodating to quick one night stays if needed."
United States
Joseph S.
$120 nightly
The price is $127
Jul 20 - Jul 21
Total with taxes and fees
Cabin 1 The Sunrise Patio
Exterior

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, (62 reviews)
"Wonderful stay. It was clean, nice area, nice view, fun decor. Bed was comfortable. Good privacy."
United States
O'Neill
$168 nightly
The price is $168
Jul 22 - Jul 23
Total with taxes and fees
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Property grounds

Charming GOTL 1 Bedroom Lake Erie Cottage, sleeps 4

Charming GOTL 1 Bedroom Lake Erie Cottage, sleeps 4
Geneva
10.0 out of 10, Exceptional, (32 reviews)
"Very nice place, check it out!"
United States
Christopher D.
$219 nightly
The price is $247
Jul 23 - Jul 24
Total with taxes and fees
Charming GOTL 1 Bedroom Lake Erie Cottage, sleeps 4
Property grounds

Charming 1-bedroom cabin in Geneva

Charming 1-bedroom cabin in Geneva
Geneva
9.8 out of 10, Exceptional, (8 reviews)
"Great out of the grid hideaway. Hosts are very nice, thanks for having us! "
United States
nina H.
$133 nightly
The price is $137
Jul 21 - Jul 22
Total with taxes and fees
Charming 1-bedroom cabin in Geneva
Property grounds

Cozy Shed-Teau in Geneva + Firepit

Cozy Shed-Teau in Geneva + Firepit
Geneva
9.4 out of 10, Exceptional, (10 reviews)
"Your place was beautiful. Unfortunately we did not get to spend the night as planned. Thank you."
United States
Lori S.
$154 nightly
The price is $154
Jul 21 - Jul 22
Total with taxes and fees
Cozy Shed-Teau in Geneva + Firepit
Free WiFi, bed sheets

Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat

Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
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
$239 nightly
The price is $239
Jul 19 - Jul 20
Total with taxes and fees
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
Interior

Nestled Inn Mespo Modern & Cozy Apartment

Nestled Inn Mespo Modern & Cozy Apartment
Middlefield
10.0 out of 10, Exceptional, (7 reviews)
"Beautiful place and very well taken care of."
United States
Andrew G.
$205 nightly
The price is $205
Jul 19 - Jul 20
Total with taxes and fees
Nestled Inn Mespo Modern & Cozy Apartment
Outdoor spa tub

Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far

Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
Madison
9.6 out of 10, Exceptional, (9 reviews)
"Super clean and cozy cabin! I can’t wait to stay again! "
United States
Alyssa T.
$239 nightly
The price is $239
Jul 19 - Jul 20
Total with taxes and fees
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
Private kitchen

Peaceful private apartment in the charming Hiram countryside

Peaceful private apartment in the charming Hiram countryside
Garrettsville
9.2 out of 10, Wonderful, (5 reviews)
"We had a wonderful experience! The bed was very comfortable and the space was beautiful and clean. We enjoyed how quiet the area was and it was perfect for our weekend getaway. We will absolutely be staying here the next time we are out this way!"
United States
Ashley
$189 nightly
The price is $191
Jul 17 - Jul 18
Total with taxes and fees
Peaceful private apartment in the charming Hiram countryside
Exterior

BB Hideaway

BB Hideaway
Geneva
9.2 out of 10, Wonderful, (5 reviews)
"We had a wonderful time place was beautiful!! Very clean! Owners were amazing above and beyond 10000/10000 definitely coming back! Thank you guys so much !!"
United States
Paige M.
$133 nightly
The price is $137
Jul 21 - Jul 22
Total with taxes and fees
BB Hideaway
TV

1br-1bth- Furnished Apartment in Chardon

1br-1bth- Furnished Apartment in Chardon
Chardon
9.6 out of 10, Exceptional, (14 reviews)
"The apartment was very nice and the hosts appointed it very well. It is a great place to stay!"
United States
Eric M.
$155 nightly
The price is $155
Jul 19 - Jul 20
Total with taxes and fees
1br-1bth- Furnished Apartment in Chardon
On the beach

LemonDrop Lake-Front Cottage

LemonDrop Lake-Front Cottage
Madison-on-the-Lake
10.0 out of 10, Exceptional, (17 reviews)
"Wife and I had a memorable stay at this charming cottage right on Lake Erie. The owners were extremely gracious and accommodating. Highly recommend for a relaxing get away!"
United Kingdom
Daniel C.
$289 nightly
The price is $289
Jul 23 - Jul 24
Total with taxes and fees
LemonDrop Lake-Front Cottage
Interior

The Riesling Cottage - GOTL Strip - Cozy & Quaint

The Riesling Cottage - GOTL Strip - Cozy & Quaint
Geneva
10.0 out of 10, Exceptional, (24 reviews)
"Very nice, clean.and cozy cottage. Would recommend to everyone. "
United States
David R
$312 nightly
The price is $320
Aug 2 - Aug 3
Total with taxes and fees
The Riesling Cottage - GOTL Strip - Cozy & Quaint
Coffee/tea maker, fridge, microwave, oven

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, (39 reviews)
"Everything was as described. It was a pleasant visit."
United States
Amy
$206 nightly
The price is $206
Jul 27 - Jul 28
Total with taxes and fees
Recently updated apartment in a Triplex unit #1 close to wineries and the lake.
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

Red Roof Inn Cleveland - Mentor/ Willoughby

Red Roof Inn Cleveland - Mentor/ Willoughby

8/10 Good
"."
James 2-night trip
Posted less than an hour ago
Red Roof Inn Cleveland - Mentor/ Willoughby

Find out more about Windsor

Everything you need to know about Windsor vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Windsor vacation 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 low season months. For more hustle and bustle, you may prefer to visit Windsor in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $43 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

Walk to Lake, Park & Strip | Pet Friendly: This vacation home rental outside of Windsor is located on a lake and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and an oven, so you can cook with friends or family.

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 Snow Lake. Windsor Mills Covered Bridge and Rothenbühler Cheese Chalet 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.