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Top Holiday Rentals in Windsor

Our top choices for Windsor holiday rentals

Historic Cottage - At Hopelands Gardens close to Hitchcock Woods (Remodeled)

10.0 out of 10, Exceptional, (90)
"A delightful and comfortable cottage next to Hopelands Gardens and convenient for exploring the town. "
Historic Cottage - At Hopelands Gardens close to Hitchcock Woods (Remodeled)

10 Acre Country Estate, Serene and Relaxing

9.0 out of 10, Wonderful, (85)
"Feels like home "
10 Acre Country Estate, Serene and Relaxing

Charming 2-bedroom cottage 3 miles from Historic downtown Aiken!

The price is £153
includes taxes & fees
4 Sept - 5 Sept
Charming 2-bedroom cottage 3 miles from Historic downtown Aiken!

5 bedroom spacious home, with charcoal grill and seating. Peaceful neighborhood.

8.8 out of 10, Excellent, (15)
"Our stay was perfect. "
The price is £206
includes taxes & fees
1 Sept - 2 Sept
5 bedroom spacious home, with charcoal grill and seating. Peaceful neighborhood.

Victory Reins- Quiet Country Stay Near Aiken, Pet Friendly,

10.0 out of 10, Exceptional, (9)
"The place was very clean and Quiet"
The price is £274
includes taxes & fees
4 Sept - 5 Sept
Victory Reins- Quiet Country Stay Near Aiken, Pet Friendly,

Trotters Cottage-Close to Bruces Field and Downtown

9.4 out of 10, Exceptional, (26)
"The small home was very nice and very clean in a local neighborhood. It was perfect for my son and myself. "
Trotters Cottage-Close to Bruces Field and Downtown

Cottage Downtown Aiken*Horse Events*Pet Friendly*Polo*Golf

10.0 out of 10, Exceptional, (79)
"The property exceeded our expectations. Plenty of room lovely and made us feel right at home"
Cottage Downtown Aiken*Horse Events*Pet Friendly*Polo*Golf

Beautiful 3BR Townhouse

3.0 star property
9.4 out of 10, Exceptional, (12)
"Clean, quiet and pleasant. A great location for a private weekend away."
Beautiful 3BR Townhouse

Downtown Aiken- The Collins Property

10.0 out of 10, Exceptional, (47)
"This was the perfect spot for our family while visiting Aiken. The home was clean, comfortable, and just as advertised with plenty of space for our family of five. We wouldnt hesitate to stay here again when we’re back in the area. "
The price is £207
includes taxes & fees
2 Sept - 3 Sept
Downtown Aiken- The Collins Property

Downtown Luxury Charleston-style Row House/near Bruce's Field/Horse District

10.0 out of 10, Exceptional, (15)
"Jordi’s and Jeff’s property was extremely clean, easy to get to and a great fit for our family stay. "
Downtown Luxury Charleston-style Row House/near Bruce's Field/Horse District

Sweet Tea Cottage- Aiken Downtown Location

9.8 out of 10, Exceptional, (17)
"We enjoyed our stay and highly recommend this rental."
Sweet Tea Cottage- Aiken Downtown Location

2 Mi to Historic Horse District: Dog-Friendly Home

9.0 out of 10, Wonderful, (2)
"House was great, needed batteries in the smoke detector, had roaches in kitchen and bathroom. Outdoor sofa covered in hair. "
2 Mi to Historic Horse District: Dog-Friendly Home

Condo located downtown Aiken that's only a 5-minute walk to the Alley!

10.0 out of 10, Exceptional, (27)
"Ideal location downtown just 5 min walk to Alley. The place was very clean and comfortable. Nice kitchen, we cooked a few meals. "
Condo located downtown Aiken that's only a 5-minute walk to the Alley!

The Loft- Downtown Aiken

10.0 out of 10, Exceptional, (123)
"Great spot to stay in dt aiken and walk to all the restaurants and shops."
The Loft- Downtown Aiken

Country Cottage

9.8 out of 10, Exceptional, (13)
"Had a nice stay! Enjoyed staying at this property very clean and would stay again"
Country Cottage

The stylish Gentry, just minutes from downtown Aiken and Bruce's Field.

9.8 out of 10, Exceptional, (21)
"This property was awesome! Very clean and just what we needed for our trip to the Masters!"
The stylish Gentry, just minutes from downtown Aiken and Bruce's Field.

A quiet place to relax, yet close to everything. Minutes from downtown.

10.0 out of 10, Exceptional, (42)
"We needed a place to land for a couple of days and the house was wonderful. Very well stocked with items and very clean. The owner even let us know we could check in early before we left"
A quiet place to relax, yet close to everything. Minutes from downtown.

Waterfront Oasis: Relax by the Pool, Fish, Kayak, and Enjoy Fire Pit Gatherings!

9.6 out of 10, Exceptional, (60)
"Everything was perfect!"
Waterfront Oasis: Relax by the Pool, Fish, Kayak, and Enjoy Fire Pit Gatherings!

Charming 1-bedroom cottage in lovely Aiken with AC, WiFi

9.2 out of 10, Wonderful, (7)
"Great stay countryside "
Charming 1-bedroom cottage in lovely Aiken with AC, WiFi

Walk to Powderhouse Polo Fields: Aiken Getaway

9.6 out of 10, Exceptional, (10)
"The home was very clean and well maintained. It was also close to everything (stores, restaurants, things to do). Definitely recommend staying there!"
Walk to Powderhouse Polo Fields: Aiken Getaway
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

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 £153 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

Can I find a holiday rental 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?

5 bedroom spacious home, with charcoal grill and seating. Peaceful neighborhood.: This holiday home rental outside of Windsor offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Windsor?

Expedia has 4 holiday rentals for your stay in Windsor.

What’s there to see and do in Windsor?

Explore the area and family-friendly sights such as God's Acre Healing Springs, or get out into nature at a spot like Aiken State Park. Aiken Gopher Tortoise Heritage Preserve and Aiken Mall are a couple of places you'll find in the wider area.

What’s a holiday rental in Windsor like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Windsor. Holiday rentals offer extras such as kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a clean environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies bustling with people while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family gatherings.