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Our top choices for Windsor holiday rentals

The Riesling Cottage - GOTL Strip - Cozy & Quaint

The Riesling Cottage - GOTL Strip - Cozy & Quaint
Geneva
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 £154
includes taxes & fees
25 Mar - 26 Mar
The Riesling Cottage - GOTL Strip - Cozy & Quaint

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.
The price is £140
includes taxes & fees
1 Mar - 2 Mar
A great stay, close to Spire, GOTL, & Wineries....King Bed!

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, (34 reviews)
"Clean room, very nice kitchen, enjoyed my stay "
United States
Nevaeh P.
The price is £104
includes taxes & fees
1 Mar - 2 Mar
Recently updated apartment in a Triplex unit #1 close to wineries and the lake.

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, (30 reviews)
"Great Cabin! Easy to find and close to the wineries!"
United States
Sarah K.
The price is £154
includes taxes & fees
1 Mar - 2 Mar
3-bedroom cabin in country setting with AC, WiFi, 15-20 min. to local wineries.

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
9.4 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 £126
includes taxes & fees
1 Mar - 2 Mar
Rustic-Chic Woodside Cabin w/ Hot Tub & Private Deck on 450-Acre Ohio Retreat

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)
"Loved this property. Was so clean and nice. "
United States
Allyson C.
The price is £154
includes taxes & fees
1 Mar - 2 Mar
A great stay, Two, close to Spire, GOTL, & Wineries....King Bed!

GOTL Cozy Cottage- Sunset Vacation Rentals

GOTL Cozy Cottage- Sunset Vacation Rentals
Geneva
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 £169
includes taxes & fees
2 Mar - 3 Mar
GOTL Cozy Cottage- Sunset Vacation Rentals

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 £126
includes taxes & fees
1 Mar - 2 Mar
Charming Woodside Cabin w/ Private Hot Tub & Scenic Trails at Standing Rock Far

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.
The price is £152
includes taxes & fees
1 Mar - 2 Mar
Dog-Friendly Retreat Near Wineries/Spire/GOTL

GOTL Coastal Cottage- Sunset Vacation Rentals

GOTL Coastal Cottage- Sunset Vacation Rentals
Geneva
9.0 out of 10, Wonderful, (81 reviews)
"Amazing "
United States
Jessica L.
The price is £169
includes taxes & fees
1 Mar - 2 Mar
GOTL Coastal Cottage- Sunset Vacation Rentals

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 £169
includes taxes & fees
6 Mar - 7 Mar
Little house on the farm

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)
"Beautifully decorated, clean & comfy! Sweet cottage - we’ll book again!"
United States
Charlette A.
The price is £158
includes taxes & fees
1 Mar - 2 Mar
Beautiful newly remodeled cottage - Walk to strip, close to spire

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 £125
includes taxes & fees
3 Mar - 4 Mar
Quaint Cozy 1-bedroom apartment in pleasant Geneva with AC, WiFi

Strip Location | Pet Friendly | A/C | Wi-Fi & Cable | Fire Pit | Wine Country

Strip Location | Pet Friendly | A/C | Wi-Fi & Cable | Fire Pit | Wine Country
Geneva
9.6 out of 10, Exceptional, (232 reviews)
"Great house and great location!"
United States
Angela G.
The price is £132
includes taxes & fees
5 Mar - 6 Mar
Strip Location | Pet Friendly | A/C | Wi-Fi & Cable | Fire Pit | Wine Country

East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly

East End Strip: Walk to Lake & Township Park. Wine Country, Golf, Pet Friendly
Geneva
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

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.
The price is £143
includes taxes & fees
8 Mar - 9 Mar
Little oasis a short walk from GOTL strip

Peaceful private apartment in the charming Hiram countryside

Peaceful private apartment in the charming Hiram countryside
Garrettsville
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 £141
includes taxes & fees
2 Mar - 3 Mar
Peaceful private apartment in the charming Hiram countryside

Quaint cottage a short walk from the GTOL strip!

Quaint cottage a short walk from the GTOL strip!
Geneva-on-the-Lake
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 £136
includes taxes & fees
1 Mar - 2 Mar
Quaint cottage a short walk from the GTOL strip!

New Remodel |Close Lake&Park|Wine Country|Family/Pet Friendly|A/C|Wi-FiCable

New Remodel |Close Lake&Park|Wine Country|Family/Pet Friendly|A/C|Wi-FiCable
Geneva on the Lake
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 £133
includes taxes & fees
12 Mar - 13 Mar
New Remodel |Close Lake&Park|Wine Country|Family/Pet Friendly|A/C|Wi-FiCable

SeaSide Lake-Front Cottage

SeaSide Lake-Front Cottage
Madison-on-the-Lake
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 £195
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

Find out more about Windsor

Everything you need to know about Windsor holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Windsor holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windsor holiday rentals we have selected for you start as low as £89 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Windsor rentals

At Expedia, we put the best Windsor holiday 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 holiday.

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 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.