Windsor Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Windsor holiday rentals

Terrace/patio

Tiny Haven

Tiny Haven
Kinsman
10.0 out of 10, Exceptional, (27 reviews)
"The property was beautiful, the host was very generous and sweet, and it was overall, just a nice and relaxing place to get away from it all."
United States
Victor H.
The price is HK$979
HK$1,778 total
includes taxes & fees
23 Apr - 24 Apr
Tiny Haven
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.
Rome
10.0 out of 10, Exceptional, (35 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
The price is HK$979
HK$1,601 total
includes taxes & fees
22 Apr - 23 Apr
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
Smart TV, fireplace

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, (128 reviews)
"Great stay and pet friendly. Very clean and excellent, comfortable furniture. Definitely would stay again when in the area"
United States
Andrew B.
The price is HK$705
HK$1,331 total
includes taxes & fees
27 Apr - 28 Apr
Conveniently located 2 bedroom home only minutes from hiking and state park fun!
2 bedrooms, free WiFi, bed sheets

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, (39 reviews)
"Great stay"
United States
Freeman H.
The price is HK$627
HK$1,419 total
includes taxes & fees
16 Apr - 17 Apr
A great stay, close to Spire, GOTL, & Wineries....King Bed!
Interior

The Riesling Cottage - GOTL Strip - Cozy & Quaint

The Riesling Cottage - GOTL Strip - Cozy & Quaint
Geneva
10.0 out of 10, Exceptional, (21 reviews)
" Rey clean and quaint. Very easy to speak with owner."
United States
Stephanie
The price is HK$509
HK$2,195 total
includes taxes & fees
20 Apr - 21 Apr
The Riesling Cottage - GOTL Strip - Cozy & Quaint
Living area

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, (11 reviews)
"Loved this property. Was so clean and nice. "
United States
Allyson C.
The price is HK$634
HK$1,472 total
includes taxes & fees
23 Apr - 24 Apr
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
Free WiFi, bed sheets

Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat

Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
Madison
9.6 out of 10, Exceptional, (4 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$1,143
HK$1,300 total
includes taxes & fees
19 Apr - 20 Apr
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
Fridge, microwave, oven, stovetop

Dog-Friendly Retreat Near Wineries/Spire/GOTL

Dog-Friendly Retreat Near Wineries/Spire/GOTL
Madison-on-the-Lake
9.4 out of 10, Exceptional, (30 reviews)
"Great stay will be back again "
United States
andrea c.
The price is HK$768
HK$1,605 total
includes taxes & fees
16 Apr - 17 Apr
Dog-Friendly Retreat Near Wineries/Spire/GOTL
Outdoor spa tub

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
9.4 out of 10, Exceptional, (6 reviews)
"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$1,143
HK$1,300 total
includes taxes & fees
19 Apr - 20 Apr
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
Terrace/patio

Erieview Lakehouse - Lakeside Retreat in GOTL

Erieview Lakehouse - Lakeside Retreat in GOTL
Geneva
10.0 out of 10, Exceptional, (32 reviews)
"Great place, great stay!"
United States
Brett C.
The price is HK$854
HK$2,657 total
includes taxes & fees
19 Apr - 20 Apr
Erieview Lakehouse - Lakeside Retreat in GOTL
TV

GOTL Cozy Cottage- Sunset Vacation Rentals

GOTL Cozy Cottage- Sunset Vacation Rentals
Geneva
9.6 out of 10, Exceptional, (84 reviews)
"Place was very clean and welcoming. The bedrooms were nice, beds comfortable. We enjoyed our stay. "
United States
Mike B.
The price is HK$854
HK$1,802 total
includes taxes & fees
16 Apr - 17 Apr
GOTL Cozy Cottage- Sunset Vacation Rentals
On the beach

LemonDrop Lake-Front Cottage

LemonDrop Lake-Front Cottage
Madison-on-the-Lake
10.0 out of 10, Exceptional, (14 reviews)
"Wife and I had a memorable stay at this charming cottage right on Lake Erie. The owners were extremely gracious and accommodating. Highly recommend for a relaxing get away!"
United Kingdom
Daniel C.
The price is HK$1,316
HK$2,170 total
includes taxes & fees
16 Apr - 17 Apr
LemonDrop Lake-Front Cottage
Property grounds

Cozy Shed-Teau in Geneva

Cozy Shed-Teau in Geneva
Geneva
8.0 out of 10, Very good, (2 reviews)
"Your place was beautiful. Unfortunately we did not get to spend the night as planned. Thank you."
United States
Lori S.
The price is HK$861
HK$1,018 total
includes taxes & fees
22 Apr - 23 Apr
Cozy Shed-Teau in Geneva
Property grounds

Charming 1-bedroom cabin in Geneva

Charming 1-bedroom cabin in Geneva
Geneva
9.8 out of 10, Exceptional, (7 reviews)
"Great out of the grid hideaway. Hosts are very nice, thanks for having us! "
United States
nina H.
The price is HK$1,018
HK$1,215 total
includes taxes & fees
11 May - 12 May
Charming 1-bedroom cabin in Geneva
Exterior

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.
The price is HK$1,214
HK$1,754 total
includes taxes & fees
27 Apr - 28 Apr
Little house on the farm
Fridge, microwave, oven, stovetop

GOTL Coastal Cottage- Sunset Vacation Rentals

GOTL Coastal Cottage- Sunset Vacation Rentals
Geneva
9.0 out of 10, Wonderful, (81 reviews)
"Great place"
United States
Gina D.
The price is HK$854
HK$1,794 total
includes taxes & fees
23 Apr - 24 Apr
GOTL Coastal Cottage- Sunset Vacation Rentals
Outdoor dining

Beautiful cabin situated on wooded land with nice yard clearing and small stream

Beautiful cabin situated on wooded land with nice yard clearing and small stream
Madison
10.0 out of 10, Exceptional, (11 reviews)
"The location was very peaceful and relaxing. We felt at home with nature and enjoyed our time very much!"
United States
Steven B.
The price is HK$1,018
HK$1,323 total
includes taxes & fees
17 Apr - 18 Apr
Beautiful cabin situated on wooded land with nice yard clearing and small stream
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
Geneva
9.2 out of 10, Wonderful, (20 reviews)
"Super comfy bed, A/C was excellent, cute little 50’s style restaurant just down the road. "
United States
Stephanie
The price is HK$789
HK$1,455 total
includes taxes & fees
16 Apr - 17 Apr
Quaint Cozy 1-bedroom apartment in pleasant Geneva with AC, WiFi
Smart TV

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, (95 reviews)
"My wife and i absolutely love this place! Very accommodating. Will stay here again! "
United States
Seth B.
The price is HK$768
HK$1,622 total
includes taxes & fees
28 Apr - 29 Apr
Little oasis a short walk from GOTL strip
Fridge, microwave, oven, stovetop

Recently updated apartment in a Triplex unit #1 close to wineries and the lake.

Recently updated apartment in a Triplex unit #1 close to wineries and the lake.
Geneva
9.6 out of 10, Exceptional, (35 reviews)
"Clean room, very nice kitchen, enjoyed my stay "
United States
Nevaeh P.
The price is HK$564
HK$1,190 total
includes taxes & fees
16 Apr - 17 Apr
Recently updated apartment in a Triplex unit #1 close to wineries and the lake.
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

Wingate by Wyndham Geneva at SPIRE Academy

Wingate by Wyndham Geneva at SPIRE Academy

8/10 Good
"Food was fine, but no fresh fruit"
Amy 1-night trip
Posted 9 hours ago
Wingate by Wyndham Geneva at SPIRE Academy

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?

Lakefront Home Water Front Pet Friendly Steps from Winery Wi-Fi & Cable: This holiday home rental outside of Windsor is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that 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 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.