Windsor Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Windsor holiday rentals

Interior

Cottage in Geneva

The Riesling Cottage - GOTL Strip - Cozy & Quaint
9.8 out of 10, Exceptional, (19 reviews)
"Beautiful, clean, and all the amenities you could ask for. The cottage was the best! Highly recommend!"
United States
ThatSamanthaKid
The price is HK$422
HK$1,591 total
includes taxes & fees
25 Mar - 26 Mar
The Riesling Cottage - GOTL Strip - Cozy & Quaint
2 bedrooms, free WiFi, bed sheets

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$669
HK$1,475 total
includes taxes & fees
1 Mar - 2 Mar
A great stay, close to Spire, GOTL, & Wineries....King Bed!
Fridge, microwave, oven, stovetop

Apartment in Geneva

Recently updated apartment in a Triplex unit #1 close to wineries and the lake.
9.6 out of 10, Exceptional, (34 reviews)
"Clean room, very nice kitchen, enjoyed my stay "
United States
Nevaeh P.
The price is HK$444
HK$1,069 total
includes taxes & fees
1 Mar - 2 Mar
Recently updated apartment in a Triplex unit #1 close to wineries and the lake.
Dining

Cabin in Rome

3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
10.0 out of 10, Exceptional, (30 reviews)
"Great Cabin! Easy to find and close to the wineries!"
United States
Sarah K.
The price is HK$978
HK$1,623 total
includes taxes & fees
1 Mar - 2 Mar
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.
Free WiFi, bed sheets

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$1,142
HK$1,298 total
includes taxes & fees
2 Mar - 3 Mar
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat
Living area

Holiday Home in Geneva

A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
10.0 out of 10, Exceptional, (10 reviews)
"Loved this property. Was so clean and nice. "
United States
Allyson C.
The price is HK$767
HK$1,644 total
includes taxes & fees
1 Mar - 2 Mar
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!
TV

Holiday Home in Geneva

GOTL Cozy Cottage- Sunset Vacation Rentals
9.4 out of 10, Exceptional, (83 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$853
HK$1,753 total
includes taxes & fees
1 Mar - 2 Mar
GOTL Cozy Cottage- Sunset Vacation Rentals
Outdoor spa tub

Cabin in Madison

Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
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$1,142
HK$1,298 total
includes taxes & fees
1 Mar - 2 Mar
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far
Fridge, microwave, oven, stovetop

Holiday Home in Madison-on-the-Lake

Dog-Friendly Retreat Near Wineries/Spire/GOTL
9.4 out of 10, Exceptional, (29 reviews)
"Great stay will be back again "
United States
andrea c.
The price is HK$767
HK$1,580 total
includes taxes & fees
1 Mar - 2 Mar
Dog-Friendly Retreat Near Wineries/Spire/GOTL
Fridge, microwave, oven, stovetop

Holiday Home in Geneva

GOTL Coastal Cottage- Sunset Vacation Rentals
9.0 out of 10, Wonderful, (81 reviews)
"Amazing "
United States
Jessica L.
The price is HK$853
HK$1,808 total
includes taxes & fees
1 Mar - 2 Mar
GOTL Coastal Cottage- Sunset Vacation Rentals
Exterior

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$1,213
HK$1,784 total
includes taxes & fees
5 Mar - 6 Mar
Little house on the farm
Fridge, microwave, oven, stovetop

Cottage in Geneva

Beautiful newly remodeled cottage - Walk to strip, close to spire
10.0 out of 10, Exceptional, (107 reviews)
"Beautifully decorated, clean & comfy! Sweet cottage - we’ll book again!"
United States
Charlette A.
The price is HK$775
HK$1,671 total
includes taxes & fees
1 Mar - 2 Mar
Beautiful newly remodeled cottage - Walk to strip, close to spire
Fridge, microwave, oven, stovetop

Apartment in Geneva

Quaint Cozy 1-bedroom apartment in pleasant Geneva with AC, WiFi
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$613
HK$1,287 total
includes taxes & fees
3 Mar - 4 Mar
Quaint Cozy 1-bedroom apartment in pleasant Geneva with AC, WiFi
Exterior

Holiday Home in Geneva

Strip Location | Pet Friendly | A/C | Wi-Fi & Cable | Fire Pit | Wine Country
9.6 out of 10, Exceptional, (232 reviews)
"Great house and great location!"
United States
Angela G.
The price is HK$391
HK$1,369 total
includes taxes & fees
5 Mar - 6 Mar
Strip Location | Pet Friendly | A/C | Wi-Fi & Cable | Fire Pit | Wine Country
Exterior

Holiday Home in Geneva

East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly
9.4 out of 10, Exceptional, (98 reviews)
"The house was clean & had everything we needed for a long weekend!"
United States
Ashley H.
East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly
Smart TV

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$655
HK$1,508 total
includes taxes & fees
8 Mar - 9 Mar
Little oasis a short walk from GOTL strip
Private kitchen

Apartment in Garrettsville

Peaceful private apartment in the charming Hiram countryside
10.0 out of 10, Exceptional, (4 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$704
HK$1,485 total
includes taxes & fees
1 Mar - 2 Mar
Peaceful private apartment in the charming Hiram countryside
1 bedroom, free WiFi, bed sheets

Holiday Home in Geneva-on-the-Lake

Quaint cottage a short walk from the GTOL strip!
9.8 out of 10, Exceptional, (65 reviews)
"Very nice place to stay and convenient location. Very pet friendly and a nice quiet location!! "
United States
Randy F.
The price is HK$697
HK$1,425 total
includes taxes & fees
1 Mar - 2 Mar
Quaint cottage a short walk from the GTOL strip!
Exterior

Cottage in Geneva on the Lake

New Remodel |Close Lake&Park|Wine Country|Family/Pet Friendly|A/C|Wi-FiCable
9.0 out of 10, Wonderful, (105 reviews)
"Place was very cozy and clean would highly recommend and we would stay there again when we come up!"
United States
Lois B.
The price is HK$548
HK$1,374 total
includes taxes & fees
12 Mar - 13 Mar
New Remodel |Close Lake&Park|Wine Country|Family/Pet Friendly|A/C|Wi-FiCable
TV, fireplace, stereo

Apartment in Madison-on-the-Lake

SeaSide Lake-Front Cottage
10.0 out of 10, Exceptional, (12 reviews)
"The cottage is beautifully cared for and filled with little thoughtful details. The view is great and the location is perfect. We absolutely loved our stay and can't wait to go back!"
United States
Jocelyn S.
The price is HK$1,228
HK$2,065 total
includes taxes & fees
2 Mar - 3 Mar
SeaSide Lake-Front 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

Hampton Inn Ashtabula

Hampton Inn Ashtabula

10/10 Excellent
"Clean room with comfortable beds, great breakfast, just a great place to stay"
David 1-night trip
Posted 1 day ago
Hampton Inn Ashtabula

Find out more about Windsor

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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 Pioneer Waterland & Dry Fun Park, or get outside and enjoy nature at Munson Township Park. 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.