Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Windsor vacation rentals

Property grounds
Conveniently located 2 bedroom home only minutes from hiking and state park fun!

Vacation Home in Warren

Conveniently located 2 bedroom home only minutes from hiking and state park fun!
10.0 out of 10, Exceptional, (127)
"Cute little house, perfect for a long weekend stay with the family "
United States
Megan M.
$170 nightly
The price is $170
Jan 4 - Jan 5
Total with taxes and fees
Conveniently located 2 bedroom home only minutes from hiking and state park fun!
Property grounds
Ledgestone Farms-Rustic Western Getaway

Vacation Home in Warren

Ledgestone Farms-Rustic Western Getaway
8.6 out of 10, Excellent, (29)
"Clean pleasant and quiet atmosphere "
United States
Christine P.
$170 nightly
The price is $170
Jan 4 - Jan 5
Total with taxes and fees
Ledgestone Farms-Rustic Western Getaway
Fridge, microwave, oven, stovetop
Chardonnay Cottage - GOTL Strip - Cozy & Quaint

Cottage in Geneva

Chardonnay Cottage - GOTL Strip - Cozy & Quaint
9.8 out of 10, Exceptional, (12)
"Very cute & quaint. We absolutely loved it!"
United States
Magdalena
$204 nightly
The price is $208
Jan 4 - Jan 5
Total with taxes and fees
Chardonnay Cottage - GOTL Strip - Cozy & Quaint
Fridge, microwave, oven, stovetop
Ledgestone Farms-Cozy Farm Apartment

Apartment in Warren

Ledgestone Farms-Cozy Farm Apartment
9.4 out of 10, Exceptional, (51)
"Great location for a long weekend of flea marketing. Great setup."
United States
Kelly H.
$170 nightly
The price is $170
Jan 5 - Jan 6
Total with taxes and fees
Ledgestone Farms-Cozy Farm Apartment
Private kitchen
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!

Vacation Home in Geneva

A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
10.0 out of 10, Exceptional, (9)
"Loved this property. Was so clean and nice. "
United States
Allyson C.
$181 nightly
The price is $181
Jan 4 - Jan 5
Total with taxes and fees
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
Fridge, microwave, oven, stovetop
A great stay, close to Spire, GOTL, & Wineries....King Bed!

Vacation Home in Geneva

A great stay, close to Spire, GOTL, & Wineries....King Bed!
9.8 out of 10, Exceptional, (38)
"Great stay"
United States
Freeman H.
$172 nightly
The price is $172
Jan 4 - Jan 5
Total with taxes and fees
A great stay, close to Spire, GOTL, & Wineries....King Bed!
Smart TV
Little oasis a short walk from GOTL strip

Cottage in Geneva-on-the-Lake

Little oasis a short walk from GOTL strip
10.0 out of 10, Exceptional, (93)
"Great place! Nice,clean and relaxing will book again. "
United States
Tracey M.
$189 nightly
The price is $189
Jan 4 - Jan 5
Total with taxes and fees
Little oasis a short walk from GOTL strip
Dining
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.

Cabin in Rome

3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
10.0 out of 10, Exceptional, (26)
"Wonderful cabin and owners. Easily a 5/5 with lots of things to do near by"
United States
Connor
$200 nightly
The price is $208
Jan 5 - Jan 6
Total with taxes and fees
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
Fridge, microwave, oven, stovetop
Peaceful Eagle One is nestled in a quaint small town near many attractions

Vacation Home in Cortland

Peaceful Eagle One is nestled in a quaint small town near many attractions
10.0 out of 10, Exceptional, (7)
"Easy, clean , will stay again ...... "
United States
Chad M.
$165 nightly
The price is $165
Jan 12 - Jan 13
Total with taxes and fees
Peaceful Eagle One is nestled in a quaint small town near many attractions
Exterior
Beautiful newly remodeled cottage - Walk to strip, close to spire

Cottage in Geneva

Beautiful newly remodeled cottage - Walk to strip, close to spire
10.0 out of 10, Exceptional, (106)
"This cabin was absolutely amazing! The perfect get away for a girls weekend. So beautiful inside and well kept. A nice little welcome bsket abd the area qas nkce and quite. I would highly recommend this place and we are plannkng to make this cabin an annual girls get away trip! "
United States
Melissa H.
$194 nightly
The price is $209
Jan 4 - Jan 5
Total with taxes and fees
Beautiful newly remodeled cottage - Walk to strip, close to spire
Fridge, microwave, oven, stovetop
Dog-Friendly Retreat Near Wineries/Spire/GOTL

Vacation Home in Madison-on-the-Lake

Dog-Friendly Retreat Near Wineries/Spire/GOTL
9.4 out of 10, Exceptional, (29)
"Great stay will be back again "
United States
andrea c.
$193 nightly
The price is $201
Jan 4 - Jan 5
Total with taxes and fees
Dog-Friendly Retreat Near Wineries/Spire/GOTL
Microwave, oven, stovetop, coffee/tea maker
Merlot Cottage - GOTL Strip - Lover's Retreat

Apartment in Geneva

Merlot Cottage - GOTL Strip - Lover's Retreat
$176 nightly
The price is $188
Jan 4 - Jan 5
Total with taxes and fees
Merlot Cottage - GOTL Strip - Lover's Retreat
1 bedroom, WiFi, bed sheets
Peaceful private apartment in the charming Hiram countryside

Apartment in Garrettsville

Peaceful private apartment in the charming Hiram countryside
10.0 out of 10, Exceptional, (3)
"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
Jan 4 - Jan 5
Total with taxes and fees
Peaceful private apartment in the charming Hiram countryside
Fridge, microwave, oven, stovetop
GOTL Comfy Cottage- Sunset Vacation Rentals

Vacation Home in Geneva

GOTL Comfy Cottage- Sunset Vacation Rentals
2.0 star property
9.0 out of 10, Wonderful, (16)
"Very comfortable cottage. Convenient to the strip but far enough away to not have all the nighttime noise."
United States
Mary S.
$215 nightly
The price is $224
Jan 4 - Jan 5
Total with taxes and fees
GOTL Comfy Cottage- Sunset Vacation Rentals
Property grounds
The Farm at Grand River

Camping in Thompson

The Farm at Grand River
8.0 out of 10, Very Good, (4)
"Excellent spot to camp, very peaceful. We would definitely revisit if we are in the area again. Property manager(s) were very friendly and accommodating."
United States
Elizabeth W.
$50 nightly
The price is $50
Jan 4 - Jan 5
Total with taxes and fees
The Farm at Grand River
Fridge, microwave, oven, stovetop
GOTL Coastal Cottage- Sunset Vacation Rentals

Vacation Home in Geneva

GOTL Coastal Cottage- Sunset Vacation Rentals
9.0 out of 10, Wonderful, (80)
"Amazing "
United States
Jessica L.
$209 nightly
The price is $224
Jan 4 - Jan 5
Total with taxes and fees
GOTL Coastal Cottage- Sunset Vacation Rentals
Exterior detail
Little house on the farm

Vacation Home in Middlefield

Little house on the farm
10.0 out of 10, Exceptional, (94)
"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
Jan 4 - Jan 5
Total with taxes and fees
Little house on the farm
On the beach
LAKEFRONT LOFT-PERFECT COUPLES GETAWAY--rent 2 get 3rd free-until April 1- ask!

Apartment in Geneva

LAKEFRONT LOFT-PERFECT COUPLES GETAWAY--rent 2 get 3rd free-until April 1- ask!
10.0 out of 10, Exceptional, (363)
"Very clean and thanks to Debbie for great communication and the suggestion on The Little Pie shop for breakfast it was fantastic !! "
United States
jeff
$116 nightly
The price is $116
Jan 4 - Jan 5
Total with taxes and fees
LAKEFRONT LOFT-PERFECT COUPLES GETAWAY--rent 2 get 3rd free-until April 1- ask!
Property grounds
3rd Floor Lakeview 2-Bedroom Penthouse in Geneva U6

Condo in Geneva

3rd Floor Lakeview 2-Bedroom Penthouse in Geneva U6
10.0 out of 10, Exceptional, (2)
"Love this place!"
United States
Amy M.
$223 nightly
The price is $223
Jan 5 - Jan 6
Total with taxes and fees
3rd Floor Lakeview 2-Bedroom Penthouse in Geneva U6
Property grounds
Cabin 1 The Sunrise Patio

Cabin in Geneva

Cabin 1 The Sunrise Patio
9.6 out of 10, Exceptional, (7)
"Teressa and her husband were amazing hosts! We enjoyed staying in a comfy quiet place! "
United States
danielle c.
$145 nightly
The price is $154
Jan 5 - Jan 6
Total with taxes and fees
Cabin 1 The Sunrise Patio
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

Hampton Inn Ashtabula

Hampton Inn Ashtabula

10/10 Excellent
"The room was extremely clean, staff was kind and attentive, the pool are was beautifully maintained, the breakfast was delicious and full of food no matter what time you went down, and the lobby was beautifully decorated for the holidays! It was a perfect stay and I would give it more stars if I was able!"
Marisa 1-night trip
Posted 1 day ago
Hampton Inn Ashtabula

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 $116 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?

Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries: This vacation home rental outside of Windsor is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 10 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a garden.

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 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.