Windsor Holiday Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Windsor

Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Windsor you may be interested in

Kingsmill Resort

4.0 star property
8.8 out of 10, Excellent, (1088)
"Beautiful property. Spacious rooms. Excellent staff who met all of our needs. "
The price is S$303
includes taxes & fees
1 Dec - 2 Dec
Kingsmill Resort

Comfort Inn Newport News - Hampton I-64

2.5 star property
8.4 out of 10, Very good, (1098)
"Enjoyed my stay, comfortable bed"
The price is S$115
includes taxes & fees
12 Dec - 13 Dec
Comfort Inn Newport News - Hampton I-64

Courtyard by Marriott Norfolk Downtown

3.0 star property
8.2 out of 10, Very good, (1101)
"The location of this hotel is perfect for visiting downtown Norfolk. You can walk to many restaurants and attractions. The staff was very friendly and helpful and made the weekend one we won’t forget. "
The price is S$134
includes taxes & fees
8 Dec - 9 Dec
Courtyard by Marriott Norfolk Downtown
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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 Chesapeake Square Mall and Planters Peanut Center.

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.