Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Windsor vacation rentals

Dining

Cabin in Rome

3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
10.0 out of 10, Exceptional, (32 reviews)
"This was a wonderful place to stay for our family. Beds were comfy along with linens. The cabin was well stocked and all the creative personal touches made it cozy and aesthetic. We hope to make a visit again if we’re near the area. "
United States
Andrew
$199 nightly
The price is $207
Mar 15 - Mar 16
Total with taxes and fees
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
Exterior

Cabin in Geneva

Storybook Cottage in the Woods
10.0 out of 10, Exceptional, (3 reviews)
"My girlfriend and I were looking for a quiet, rural place to celebrate our anniversary and we found the perfect place, we even enjoyed bowling a few games just down the road!!"
United States
Joseph
$315 nightly
The price is $356
Mar 15 - Mar 16
Total with taxes and fees
Storybook Cottage in the Woods
Exterior

Vacation Home in Middlefield

Little house on the farm
10.0 out of 10, Exceptional, (94 reviews)
"My stay here was wonderful! James and Anna were very welcoming and such a clean place when arriving! I love this area as I grew up here and was close to many destinations I had planned. I will definitely be returning again."
United States
Sarah S.
$226 nightly
The price is $226
Mar 19 - Mar 20
Total with taxes and fees
Little house on the farm
Smart TV, fireplace

Cabin in Geneva

Peaceful 3BR Cabin Retreat w/Hot Tub-Near Wineries, Geneva-on-the-Lake & Spire
10.0 out of 10, Exceptional, (13 reviews)
"Was a great stay!"
United States
James S.
$398 nightly
The price is $398
Mar 22 - Mar 23
Total with taxes and fees
Peaceful 3BR Cabin Retreat w/Hot Tub-Near Wineries, Geneva-on-the-Lake & Spire
Property grounds

Vacation Home in Waite Hill

Old Orchard Kirtland, Ohio
9.8 out of 10, Exceptional, (7 reviews)
"Wonderful hospitality!! Very clean. Great owners!!"
United States
Christa K.
$305 nightly
The price is $305
Mar 14 - Mar 15
Total with taxes and fees
Old Orchard Kirtland, Ohio
Outdoor spa tub

Cottage in Madison

Vineyard View | Walk to Wineries & River| Hot Tub
10.0 out of 10, Exceptional, (66 reviews)
"Great amenities and beautiful setting"
United States
Joyce L.
$440 nightly
The price is $459
Mar 15 - Mar 16
Total with taxes and fees
Vineyard View | Walk to Wineries & River| Hot Tub
Interior

Cabin in Madison

Woodside Cabins w/ Hot Tub, Deck & Trails on Picturesque Wine Country Estate
10.0 out of 10, Exceptional, (1 review)
"The cabin was great, situated along the woods, lots of privacy, nice hot tub, cozy, very comfy king sized bed, an excellent getaway for a few days. Good places to walk, nice farm animals to pet, etc. "
United States
Rick
$166 nightly
The price is $166
Mar 15 - Mar 16
Total with taxes and fees
Woodside Cabins w/ Hot Tub, Deck & Trails on Picturesque Wine Country Estate
TV, fireplace, stereo

Apartment in Madison-on-the-Lake

SeaSide Lake-Front Cottage
10.0 out of 10, Exceptional, (12 reviews)
"The cottage is beautifully cared for and filled with little thoughtful details. The view is great and the location is perfect. We absolutely loved our stay and can't wait to go back!"
United States
Jocelyn S.
$262 nightly
The price is $262
Mar 15 - Mar 16
Total with taxes and fees
SeaSide Lake-Front Cottage
Dining

Vacation Home in Geneva

Centrally located local wineries, GOTL, and Spire. Walk to winery, coffeehouse
10.0 out of 10, Exceptional, (39 reviews)
"Great place to stay in Geneva. Centrally located for wineries, downtown Geneva and covered bridges"
United States
Scott B.
$417 nightly
The price is $446
Mar 15 - Mar 16
Total with taxes and fees
Centrally located local wineries, GOTL, and Spire. Walk to winery, coffeehouse
Fridge, microwave, oven, stovetop

Cottage in Newbury

Country Cottage Farm Stay at Stoneycreek Acres
10.0 out of 10, Exceptional, (72 reviews)
"Loved our stay!! Clean and wonderful! "
United States
Amber S.
$346 nightly
The price is $346
Mar 16 - Mar 17
Total with taxes and fees
Country Cottage Farm Stay at Stoneycreek Acres
Interior

Apartment in Middlefield

Nestled Inn Mespo Modern & Cozy Apartment
10.0 out of 10, Exceptional, (6 reviews)
"Emily and Austin have a great apartment. It felt like being home; super clean, a ton of amenities, comfortable bed; anything you think you need they had it. Great location to Middlefield and surrounding areas; Will be using them in the future when in town to visit family. "
United States
alicia t.
$202 nightly
The price is $202
Mar 15 - Mar 16
Total with taxes and fees
Nestled Inn Mespo Modern & Cozy Apartment
Private kitchen

Apartment in Garrettsville

Peaceful private apartment in the charming Hiram countryside
10.0 out of 10, Exceptional, (4 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
$188 nightly
The price is $190
Mar 14 - Mar 15
Total with taxes and fees
Peaceful private apartment in the charming Hiram countryside
Interior

Vacation Home in Painesville

Family-friendly 5-Star Rated 19th Century Restored Mansion
10.0 out of 10, Exceptional, (35 reviews)
"This property was lovely and suited our needs perfectly. We were ten siblings with some of the spouses - several were local and did not stay overnight. It was like a step back in time but with all the modern amenities. The owner was gracious and welcoming and we hope to be back next year!"
United States
Kathy M.
$839 nightly
The price is $930
Mar 14 - Mar 15
Total with taxes and fees
Family-friendly 5-Star Rated 19th Century Restored Mansion
Smart TV, offices

Vacation Home in Garrettsville

Small town vibes in Garrettsville
10.0 out of 10, Exceptional, (3 reviews)
"Very clean, solid rental. "
United States
Christopher P.
$393 nightly
The price is $393
Mar 14 - Mar 15
Total with taxes and fees
Small town vibes in Garrettsville
Interior

Vacation Home in Mantua

Peaceful Pioneer Place on our Family Farm in Mantua
9.6 out of 10, Exceptional, (5 reviews)
"We had a great time!! The home has a beautiful lay out and we were very comfortable!!!"
United States
Pamela M.
$486 nightly
The price is $486
Mar 16 - Mar 17
Total with taxes and fees
Peaceful Pioneer Place on our Family Farm in Mantua
Exterior

Cottage in Geneva

3 Little Cottages - #1 Sundance Cottage
9.6 out of 10, Exceptional, (42 reviews)
"Great little place in Geneva on the lake. Would definitely stay here again. Everything you need for a quick stay and the host was more than accommodating with any of our requests."
United States
Richard
$264 nightly
The price is $286
Mar 20 - Mar 21
Total with taxes and fees
3 Little Cottages - #1 Sundance Cottage
Private kitchen

Vacation Home in Garrettsville

Lovely private 3 bedroom house nestled in the Hiram countryside.
9.0 out of 10, Wonderful, (9 reviews)
"Clean, large and quiet place."
United States
Michelle T.
$349 nightly
The price is $353
Mar 14 - Mar 15
Total with taxes and fees
Lovely private 3 bedroom house nestled in the Hiram countryside.
Beach nearby, sun loungers

Vacation Home in Geneva

House 1 mile from Geneva on Lake. We have several wineries in the area.
10.0 out of 10, Exceptional, (29 reviews)
"Great house and great location!"
United States
John G.
$286 nightly
The price is $286
Mar 16 - Mar 17
Total with taxes and fees
House 1 mile from Geneva on Lake. We have several wineries in the area.
On the beach

Cabin in Madison-on-the-Lake

LemonDrop Lake-Front Cottage
10.0 out of 10, Exceptional, (14 reviews)
"Great little place on the lake. We lived our stay."
United States
robin c.
$259 nightly
The price is $259
Apr 1 - Apr 2
Total with taxes and fees
LemonDrop Lake-Front Cottage
Smart TV, Netflix, books, streaming services

Vacation Home in Geneva

Renovated 4-Bedroom Home in Geneva, Ohio • Wineries • SPIRE Institute • GOTL
10.0 out of 10, Exceptional, (16 reviews)
"The house was wonderful, decorated very nicely and had everything we could have needed for our long weekend. It was a nice & quiet neighborhood, even being next to the train tracks, which didn't bother any of us. Becky was very responsive and answered any questions I had in a timely fashion."
United States
Tina M.
$396 nightly
The price is $427
Mar 16 - Mar 17
Total with taxes and fees
Renovated 4-Bedroom Home in Geneva, Ohio • Wineries • SPIRE Institute • GOTL
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

The Lodge at Geneva

The Lodge at Geneva

10/10 Excellent
"They had a power outage because of a storm but were kind and supportive. 10/10"
Tabitha 1-night trip
Posted 22 hours ago
The Lodge at Geneva

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 $122 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?

Strip Location | Pet Friendly | A/C | Wi-Fi & Cable | Fire Pit | Wine Country: This vacation home rental outside of Windsor is located on a lake and has a garden, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, 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 Munson Township Park. Windsor Mills Covered Bridge and Huntsburg Town Hall 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.