Windsor Vacation Rentals

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Check prices for these dates

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Windsor vacation rentals

Property grounds
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!

Conveniently located 2 bedroom home only minutes from hiking and state park fun!
Warren
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
Dec 31 - Jan 1, 2026
Total with taxes and fees
Conveniently located 2 bedroom home only minutes from hiking and state park fun!
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.

3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
Rome
10.0 out of 10, Exceptional, (25)
"Wonderful cabin and owners. Easily a 5/5 with lots of things to do near by"
United States
Connor
$198 nightly
The price is $206
Jan 4 - Jan 5, 2026
Total with taxes and fees
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
Private kitchen
1st Floor Beach Access 2-Bedroom Condo in Geneva U2

1st Floor Beach Access 2-Bedroom Condo in Geneva U2

1st Floor Beach Access 2-Bedroom Condo in Geneva U2
Geneva
10.0 out of 10, Exceptional, (2)
"We had an excellent stay. The property was very clean. Looks like it was recently renovated and it’s at the east end of the strip and quieter. The host was prompt in responding. We didn’t need much as we only stayed one night. I wish we stayed a couple nights. Would love to come back. "
United States
William S.
$223 nightly
The price is $223
Dec 29 - Dec 30
Total with taxes and fees
1st Floor Beach Access 2-Bedroom Condo in Geneva U2
Fridge, microwave, oven, stovetop
Peaceful Eagle One is nestled in a quaint small town near many attractions

Peaceful Eagle One is nestled in a quaint small town near many attractions

Peaceful Eagle One is nestled in a quaint small town near many attractions
Cortland
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, 2026
Total with taxes and fees
Peaceful Eagle One is nestled in a quaint small town near many attractions
Fridge, microwave, oven, stovetop
Ledgestone Farms-Quiet Country Apartment

Ledgestone Farms-Quiet Country Apartment

Ledgestone Farms-Quiet Country Apartment
Warren
9.2 out of 10, Wonderful, (39)
"It was a good stay for my boyfriend and I, we enjoyed the quiet and the jacuzzi tub was wonderful!"
United States
Remi r.
$140 nightly
The price is $140
Jan 2 - Jan 3, 2026
Total with taxes and fees
Ledgestone Farms-Quiet Country Apartment
Outdoor dining
Keys cottage -walk to the strip,Private lot, 2bdr 3rd guestroom detached.Spire

Keys cottage -walk to the strip,Private lot, 2bdr 3rd guestroom detached.Spire

Keys cottage -walk to the strip,Private lot, 2bdr 3rd guestroom detached.Spire
Geneva
10.0 out of 10, Exceptional, (106)
"Beautiful cottage just as described. Will stay again."
United States
Anonymous traveler
$216 nightly
The price is $216
Dec 28 - Dec 29
Total with taxes and fees
Keys cottage -walk to the strip,Private lot, 2bdr 3rd guestroom detached.Spire
Fridge, microwave, oven, stovetop
Quaint Cozy 1-bedroom apartment in pleasant Geneva with AC, WiFi

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

Quaint Cozy 1-bedroom apartment in pleasant Geneva with AC, WiFi
2.0 star property
Geneva
9.2 out of 10, Wonderful, (20)
"Super comfy bed, A/C was excellent, cute little 50’s style restaurant just down the road. "
United States
Stephanie
$167 nightly
The price is $173
Dec 28 - Dec 29
Total with taxes and fees
Quaint Cozy 1-bedroom apartment in pleasant Geneva with AC, WiFi
Fridge, microwave, oven, stovetop
Nestled Inn Mespo Modern & Cozy Apartment

Nestled Inn Mespo Modern & Cozy Apartment

Nestled Inn Mespo Modern & Cozy Apartment
Middlefield
10.0 out of 10, Exceptional, (3)
"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.
$203 nightly
The price is $203
Dec 28 - Dec 29
Total with taxes and fees
Nestled Inn Mespo Modern & Cozy Apartment
Property grounds
Charming 1-bedroom cabin in Geneva

Charming 1-bedroom cabin in Geneva

Charming 1-bedroom cabin in Geneva
Geneva
9.8 out of 10, Exceptional, (7)
"Great out of the grid hideaway. Hosts are very nice, thanks for having us! "
United States
nina H.
$133 nightly
The price is $140
Dec 31 - Jan 1, 2026
Total with taxes and fees
Charming 1-bedroom cabin in Geneva
Fridge, microwave, oven, stovetop
Ledgestone Farms-Cozy Farm Apartment

Ledgestone Farms-Cozy Farm Apartment

Ledgestone Farms-Cozy Farm Apartment
Warren
9.4 out of 10, Exceptional, (51)
"Great location for a long weekend of flea marketing. Great setup."
United States
Kelly H.
$140 nightly
The price is $140
Dec 30 - Dec 31
Total with taxes and fees
Ledgestone Farms-Cozy Farm Apartment
Exterior detail
Little house on the farm

Little house on the farm

Little house on the farm
Middlefield
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 2 - Jan 3, 2026
Total with taxes and fees
Little house on the farm
Exterior
Woodside Cabins w/ Hot Tub, Deck & Trails on Picturesque Wine Country Estate

Woodside Cabins w/ Hot Tub, Deck & Trails on Picturesque Wine Country Estate

Woodside Cabins w/ Hot Tub, Deck & Trails on Picturesque Wine Country Estate
Madison
10.0 out of 10, Exceptional, (1)
"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
Woodside Cabins w/ Hot Tub, Deck & Trails on Picturesque Wine Country Estate
1 bedroom, WiFi, bed sheets
Peaceful private apartment in the charming Hiram countryside

Peaceful private apartment in the charming Hiram countryside

Peaceful private apartment in the charming Hiram countryside
Garrettsville
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
$189 nightly
The price is $191
Dec 29 - Dec 30
Total with taxes and fees
Peaceful private apartment in the charming Hiram countryside
Exterior
Beautiful newly remodeled cottage - Walk to strip, close to spire

Beautiful newly remodeled cottage - Walk to strip, close to spire

Beautiful newly remodeled cottage - Walk to strip, close to spire
Geneva
10.0 out of 10, Exceptional, (106)
"Perfect place ! Cozy and comfy ! Amazing host ! "
United States
Roberta T.
$199 nightly
The price is $214
Dec 28 - Dec 29
Total with taxes and fees
Beautiful newly remodeled cottage - Walk to strip, close to spire
Fridge, microwave, oven, stovetop
GOTL Comfy Cottage- Sunset Vacation Rentals

GOTL Comfy Cottage- Sunset Vacation Rentals

GOTL Comfy Cottage- Sunset Vacation Rentals
2.0 star property
Geneva
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.
$216 nightly
The price is $225
Dec 29 - Dec 30
Total with taxes and fees
GOTL Comfy Cottage- Sunset Vacation Rentals
Property grounds
Cabin 1 The Sunrise Patio

Cabin 1 The Sunrise Patio

Cabin 1 The Sunrise Patio
Geneva
9.6 out of 10, Exceptional, (7)
"Atmosphere cabin property and hosts where exceptional!Recommend contacting host before booking they are off grid (no electric, running water or sewer) "
United States
Lora S.
$145 nightly
The price is $154
Dec 28 - Dec 29
Total with taxes and fees
Cabin 1 The Sunrise Patio
Property grounds
SeaSide Lake-Front Cottage

SeaSide Lake-Front Cottage

SeaSide Lake-Front Cottage
Madison-on-the-Lake
10.0 out of 10, Exceptional, (12)
"Beautiful property! The owners thought of everything that a renter may need and went above and beyond to deliver. The view was greatly enjoyed and the sunsets are incredible at this location. We were very happy at how centrally located this place was to Geneva on the Lake, many close wineries and walking trails. Looking forward to staying here again! "
United States
Heidi C.
$262 nightly
The price is $262
Dec 30 - Dec 31
Total with taxes and fees
SeaSide Lake-Front Cottage
Fridge, microwave, oven, stovetop
The Riesling Cottage - GOTL Strip - Cozy & Quaint

The Riesling Cottage - GOTL Strip - Cozy & Quaint

The Riesling Cottage - GOTL Strip - Cozy & Quaint
Geneva
9.8 out of 10, Exceptional, (19)
"Beautiful, clean, and all the amenities you could ask for. The cottage was the best! Highly recommend!"
United States
ThatSamanthaKid
$204 nightly
The price is $208
Jan 22 - Jan 23, 2026
Total with taxes and fees
The Riesling Cottage - GOTL Strip - Cozy & Quaint
Smart TV, fireplace
Peaceful 3BR Cabin Retreat w/Hot Tub-Near Wineries, Geneva-on-the-Lake & Spire

Peaceful 3BR Cabin Retreat w/Hot Tub-Near Wineries, Geneva-on-the-Lake & Spire

Peaceful 3BR Cabin Retreat w/Hot Tub-Near Wineries, Geneva-on-the-Lake & Spire
Geneva
10.0 out of 10, Exceptional, (10)
"Was a great stay!"
United States
James S.
$349 nightly
The price is $349
Jan 4 - Jan 5, 2026
Total with taxes and fees
Peaceful 3BR Cabin Retreat w/Hot Tub-Near Wineries, Geneva-on-the-Lake & Spire
Exterior
3 Little Cottages - #1 Sundance Cottage

3 Little Cottages - #1 Sundance Cottage

3 Little Cottages - #1 Sundance Cottage
Geneva
9.6 out of 10, Exceptional, (42)
"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
Jan 2 - Jan 3, 2026
Total with taxes and fees
3 Little Cottages - #1 Sundance Cottage
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

Comfort Inn

Comfort Inn

10/10 Excellent
"Staff was very courteous and helpful."
ROBERT 1-night trip
Posted 4 days ago
Comfort Inn

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 $130 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.