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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Windsor holiday rentals

A modern courtyard with white furniture, a central seating area, and a small lawn.

1. stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (110 reviews)
"Theophilus was great at check in. Amazing customer service, quick check-in. The place was clean, the rooms were very clean. The overall atmosphere was great. I will definitely stay here again."
United States
Tarina
The price is ฿3,990
฿4,582 total
includes taxes & fees
19 Oct - 20 Oct
stayAPT Suites Suffolk-Chesapeake
A multi-story building with balconies, a courtyard with seating, and a well-maintained lawn.

2. stayAPT Suites Hampton

stayAPT Suites Hampton
2.5 star property
Coliseum Central
9.2 out of 10, Wonderful, (25 reviews)
"Great stay! Comfortable & close to a lot of stores & restaurants"
United States
Vanessa
The price is ฿3,990
฿4,656 total
includes taxes & fees
12 Oct - 13 Oct
stayAPT Suites Hampton
A pool table in a room with wooden floors, a fireplace, and a window with purple curtains.

3. Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
The price is ฿9,757
฿20,755 total
includes taxes & fees
5 Nov - 6 Nov
Centrally Located Hampton Roads Home w/ Game Room!
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

Hilton Norfolk The Main

Hilton Norfolk The Main

10/10 Excellent
"Room was great, nice view. Affordable dinner options within easy walking distance. Very convenient to the cruise terminal."
Craig 1-night trip
Posted less than an hour ago
Hilton Norfolk The Main

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

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 can I see and do in Windsor?

Cultural attractions include Boykin's Tavern, whereas Lake Prince is a spot to enjoy nature. In the wider area, you’ll find Windsor Castle Park and Chesapeake Square Mall.

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 provide amenities such as kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family trip.