Windsor Holiday Rentals

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Check prices for these dates

Tonight
13 Jan - 14 Jan
Tomorrow
14 Jan - 15 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

Our top choices for Windsor holiday rentals

Outdoor dining
The Farm at Grand River

Camping in Thompson

The Farm at Grand River
8.0 out of 10, Very good, (4 reviews)
"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.
The price is HK$234
HK$390 total
includes taxes & fees
21 Jan - 22 Jan
The Farm at Grand River
Smart TV, fireplace
Conveniently located 2 bedroom home only minutes from hiking and state park fun!

Holiday Home in Warren

Conveniently located 2 bedroom home only minutes from hiking and state park fun!
10.0 out of 10, Exceptional, (127 reviews)
"Cute little house, perfect for a long weekend stay with the family "
United States
Megan M.
The price is HK$702
HK$1,333 total
includes taxes & fees
17 Jan - 18 Jan
Conveniently located 2 bedroom home only minutes from hiking and state park fun!
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 reviews)
"Very cute & quaint. We absolutely loved it!"
United States
Magdalena
The price is HK$421
HK$1,624 total
includes taxes & fees
25 Jan - 26 Jan
Chardonnay Cottage - GOTL Strip - Cozy & Quaint
2 bedrooms, free WiFi, bed sheets
A great stay, close to Spire, GOTL, & Wineries....King Bed!

Holiday Home in Geneva

A great stay, close to Spire, GOTL, & Wineries....King Bed!
9.8 out of 10, Exceptional, (38 reviews)
"Great stay"
United States
Freeman H.
The price is HK$561
HK$1,341 total
includes taxes & fees
14 Jan - 15 Jan
A great stay, close to Spire, GOTL, & Wineries....King Bed!
Living area
1st Floor Beach Access 2-Bedroom Condo in Geneva U2

Condo in Geneva

1st Floor Beach Access 2-Bedroom Condo in Geneva U2
10.0 out of 10, Exceptional, (2 reviews)
"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.
The price is HK$982
HK$1,730 total
includes taxes & fees
14 Jan - 15 Jan
1st Floor Beach Access 2-Bedroom Condo in Geneva U2
Living area
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!

Holiday Home in Geneva

A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
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.
The price is HK$575
HK$1,417 total
includes taxes & fees
22 Jan - 23 Jan
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
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 reviews)
"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
The price is HK$585
HK$858 total
includes taxes & fees
25 Jan - 26 Jan
LAKEFRONT LOFT-PERFECT COUPLES GETAWAY--rent 2 get 3rd free-until April 1- ask!
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 reviews)
"Great place! Nice,clean and relaxing will book again. "
United States
Tracey M.
The price is HK$631
HK$1,473 total
includes taxes & fees
25 Jan - 26 Jan
Little oasis a short walk from GOTL strip
1 bedroom, desk, iron/ironing board, WiFi
Merlot Cottage - GOTL Strip - Lover's Retreat

Apartment in Geneva

Merlot Cottage - GOTL Strip - Lover's Retreat
The price is HK$421
HK$1,468 total
includes taxes & fees
25 Jan - 26 Jan
Merlot Cottage - GOTL Strip - Lover's Retreat
Interior
Lake Erie Retreat – Hidden Village Escape

Holiday Home in Perry

Lake Erie Retreat – Hidden Village Escape
10.0 out of 10, Exceptional, (1 review)
"Everything was there that we needed it was a very nice home definitely stay again"
United States
Richard P.
The price is HK$858
HK$2,546 total
includes taxes & fees
18 Jan - 19 Jan
Lake Erie Retreat – Hidden Village Escape
Exterior
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm

Apartment in Burton

Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
10.0 out of 10, Exceptional, (51 reviews)
"Very nice stay,just as described !!"
United States
Christine K.
The price is HK$673
HK$1,063 total
includes taxes & fees
26 Jan - 27 Jan
Stay in our cozy Maple Syrup Sugarhouse at Butternut Maple Farm
Private kitchen
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 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
The price is HK$702
HK$1,464 total
includes taxes & fees
18 Jan - 19 Jan
Peaceful private apartment in the charming Hiram countryside
Fridge, microwave, oven, stovetop
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 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.
The price is HK$772
HK$1,665 total
includes taxes & fees
22 Jan - 23 Jan
Beautiful newly remodeled cottage - Walk to strip, close to spire
Exterior
Little house on the farm

Holiday 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.
The price is HK$1,208
HK$1,762 total
includes taxes & fees
15 Jan - 16 Jan
Little house on the farm
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, (27 reviews)
"Wonderful cabin and owners. Easily a 5/5 with lots of things to do near by"
United States
Connor
The price is HK$974
HK$1,625 total
includes taxes & fees
16 Jan - 17 Jan
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
Interior
Charming 2-bedroom Suite with balcony overlooking the Lake in Fairport Harbor

Aparthotel in Fairport Harbor

Charming 2-bedroom Suite with balcony overlooking the Lake in Fairport Harbor
2.0 star property
9.4 out of 10, Exceptional, (13 reviews)
"Was very cozy, quiet and well kept. Would stay there again."
United States
Christopher
The price is HK$998
HK$1,348 total
includes taxes & fees
23 Jan - 24 Jan
Charming 2-bedroom Suite with balcony overlooking the Lake in Fairport Harbor
Fridge, microwave, oven, stovetop
Peaceful Eagle One is nestled in a quaint small town near many attractions

Holiday Home in Cortland

Peaceful Eagle One is nestled in a quaint small town near many attractions
10.0 out of 10, Exceptional, (7 reviews)
"Easy, clean , will stay again ...... "
United States
Chad M.
The price is HK$857
HK$1,286 total
includes taxes & fees
14 Jan - 15 Jan
Peaceful Eagle One is nestled in a quaint small town near many attractions
Free WiFi, bed sheets
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat

Cabin in Madison

Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
9.4 out of 10, Exceptional, (3 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
The price is HK$1,138
HK$1,301 total
includes taxes & fees
22 Jan - 23 Jan
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
Smart TV
Linny's GOTL Cottages "Blue Pearl" 3-bedroom house on the strip in GOTL, spire

Holiday Home in Geneva

Linny's GOTL Cottages "Blue Pearl" 3-bedroom house on the strip in GOTL, spire
10.0 out of 10, Exceptional, (13 reviews)
"Everything was absolutely perfect!"
United States
Charles
The price is HK$772
HK$1,723 total
includes taxes & fees
25 Jan - 26 Jan
Linny's GOTL Cottages "Blue Pearl" 3-bedroom house on the strip in GOTL, spire
Outdoor spa tub
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far

Cabin in Madison

Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
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
The price is HK$1,138
HK$1,301 total
includes taxes & fees
26 Jan - 27 Jan
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
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
"Room was clean, front desk associate kind, beautiful location. Resort fee should be waived due to season. Can’t enjoy full amenities in the dead of winter. "
Beth 1-night trip
Posted 5 days ago
The Lodge at Geneva

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia! You can easily find your home rentals, villas, holiday apartments in Windsor using one of the methods below:

  • View our selection of featured holiday rentals in Windsor
  • Use the map to find apartments and other holiday homes in the Windsor neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Windsor while they last

Look no further and take a look at our great range of rental properties in Windsor!

Frequently asked questions

Are there holiday rentals in Windsor?

Yes, there are holiday rentals close to the most popular sights in Windsor, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Windsor has to offer?

Private Lake Access | Pet Friendly | Wi-Fi & Cable | A/C | Fire Pit | Wineries: This holiday home rental outside of Windsor is located on the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden.

What can I see and do in Windsor?

While exploring the area, visit family-friendly sights like Middlefield Cheese Chalet Shop, 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 wider area.

What are holiday rentals like in Windsor?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Windsor. Holiday rentals feature extras like WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great choice for family trips.