Windsor Vacation Rentals

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Our top choices for Windsor vacation rentals

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 reviews)
"Cute little house, perfect for a long weekend stay with the family "
United States
Megan M.
$170 nightly
The price is $170
Jan 21 - Jan 22
Total with taxes and fees
Conveniently located 2 bedroom home only minutes from hiking and state park fun!

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 reviews)
"Easy, clean , will stay again ...... "
United States
Chad M.
$165 nightly
The price is $165
Jan 23 - Jan 24
Total with taxes and fees
Peaceful Eagle One is nestled in a quaint small town near many attractions

The Riesling Cottage - GOTL Strip - Cozy & Quaint

The Riesling Cottage - GOTL Strip - Cozy & Quaint
Geneva
9.8 out of 10, Exceptional, (19 reviews)
"Working with the Host was a wonderful experience. We found the cottage VERY clean. Kitchen was very well equipped. The road noise in evening was a little loud but did quiet down after 10 p.m. "
United States
Nancy H.
$203 nightly
The price is $207
Jan 22 - Jan 23
Total with taxes and fees
The Riesling Cottage - GOTL Strip - Cozy & Quaint

Charming 2-bedroom Suite with balcony overlooking the Lake in Fairport Harbor

Charming 2-bedroom Suite with balcony overlooking the Lake in Fairport Harbor
2.0 star property
Fairport Harbor
9.4 out of 10, Exceptional, (13 reviews)
"Was very cozy, quiet and well kept. Would stay there again."
United States
Christopher
$173 nightly
The price is $173
Jan 21 - Jan 22
Total with taxes and fees
Charming 2-bedroom Suite with balcony overlooking the Lake in Fairport Harbor

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 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
Jan 26 - Jan 27
Total with taxes and fees
Woodside Cabins w/ Hot Tub, Deck & Trails on Picturesque Wine Country Estate

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, (28 reviews)
"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 22 - Jan 23
Total with taxes and fees
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.

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, (10 reviews)
"Great stay!!! The home was so cleans cozy. Safe neighborhood. Would definitely stay here again. Anthony was very accommodating. "
United States
Nicole B.
$189 nightly
The price is $189
Feb 1 - Feb 2
Total with taxes and fees
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!

A great stay, close to Spire, GOTL, & Wineries....King Bed!

A great stay, close to Spire, GOTL, & Wineries....King Bed!
Geneva
9.8 out of 10, Exceptional, (38 reviews)
"Great stay"
United States
Freeman H.
$173 nightly
The price is $173
Jan 21 - Jan 22
Total with taxes and fees
A great stay, close to Spire, GOTL, & Wineries....King Bed!

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, (107 reviews)
"We had a wonderful stay. The home was just as pictured. Very cozy and cute. We would definitely stay here again."
United States
Shannon F.
$199 nightly
The price is $214
Jan 21 - Jan 22
Total with taxes and fees
Beautiful newly remodeled cottage - Walk to strip, close to spire

Little house on the farm

Little house on the farm
Middlefield
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
Jan 21 - Jan 22
Total with taxes and fees
Little house on the farm

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
10.0 out of 10, Exceptional, (1 review)
"The property is amazing, as is the cabin. Love the decor. We appreciated the privacy, the hot tub worked great. We also appreciated the fire ring with everything needed to build a fire! We had a lovely visit with a great friend, daughter, and her grandson that live in the area. Thanks for everything!"
United States
Jeannie
$166 nightly
The price is $166
Jan 26 - Jan 27
Total with taxes and fees
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far

Little oasis a short walk from GOTL strip

Little oasis a short walk from GOTL strip
Geneva-on-the-Lake
10.0 out of 10, Exceptional, (93 reviews)
"Great place! Nice,clean and relaxing will book again. "
United States
Tracey M.
$190 nightly
The price is $190
Jan 21 - Jan 22
Total with taxes and fees
Little oasis a short walk from GOTL strip

Dog-Friendly Retreat Near Wineries/Spire/GOTL

Dog-Friendly Retreat Near Wineries/Spire/GOTL
Madison-on-the-Lake
9.4 out of 10, Exceptional, (29 reviews)
"Great stay will be back again "
United States
andrea c.
$195 nightly
The price is $203
Jan 21 - Jan 22
Total with taxes and fees
Dog-Friendly Retreat Near Wineries/Spire/GOTL

Peaceful private apartment in the charming Hiram countryside

Peaceful private apartment in the charming Hiram countryside
Garrettsville
10.0 out of 10, Exceptional, (3 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
$185 nightly
The price is $187
Jan 21 - Jan 22
Total with taxes and fees
Peaceful private apartment in the charming Hiram countryside

Cozy One Room Studio in Wine Country!

Cozy One Room Studio in Wine Country!
Jefferson
10.0 out of 10, Exceptional, (1 review)
"This property is remote- there are attractions within a half hour drive, so if you’re hoping to walk to nearby places, this isn’t the one. Everything is much higher quality than I typically see in a VRBO rental. The bed was so comfy I didn’t want to get up! The shower is nice and the couple who own the house are very nice and accommodating "
United States
Jessica B.
$238 nightly
The price is $241
Jan 23 - Jan 24
Total with taxes and fees
Cozy One Room Studio in Wine Country!

GOTL Lovers Chateau Cottage U7

GOTL Lovers Chateau Cottage U7
Geneva
10.0 out of 10, Exceptional, (3 reviews)
"Great property and great location"
United States
Amy D.
$223 nightly
The price is $223
Jan 26 - Jan 27
Total with taxes and fees
GOTL Lovers Chateau Cottage U7

GOTL Lakeview Loft- Sunset Vacation Rentals

GOTL Lakeview Loft- Sunset Vacation Rentals
Geneva
9.6 out of 10, Exceptional, (64 reviews)
"Had a great time… very relaxing"
United States
PETER A.
$159 nightly
The price is $170
Feb 9 - Feb 10
Total with taxes and fees
GOTL Lakeview Loft- Sunset Vacation Rentals

GOTL Coastal Cottage- Sunset Vacation Rentals

GOTL Coastal Cottage- Sunset Vacation Rentals
Geneva
9.0 out of 10, Wonderful, (80 reviews)
"Amazing "
United States
Jessica L.
$209 nightly
The price is $224
Jan 21 - Jan 22
Total with taxes and fees
GOTL Coastal Cottage- Sunset Vacation Rentals

Updated Cottage - Great Location Near Lake, Wineries, and SPIRE Institute!

Updated Cottage - Great Location Near Lake, Wineries, and SPIRE Institute!
Madison-on-the-Lake
10.0 out of 10, Exceptional, (4 reviews)
"Good location and a cute space. "
United States
Veronica K.
$318 nightly
The price is $332
Jan 26 - Jan 27
Total with taxes and fees
Updated Cottage - Great Location Near Lake, Wineries, and SPIRE Institute!

Cabin 1 The Sunrise Patio

Cabin 1 The Sunrise Patio
Geneva
9.6 out of 10, Exceptional, (7 reviews)
"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 22 - Jan 23
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

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 $110 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.

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.