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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Windsor vacation 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, (107 reviews)
"The front desk staff were friendly, welcoming and helpful. The property and room were very clean and quiet. The bed was comfortable, and the room was spacious with a full kitchen. Location is very convenient to restaurants and shopping. Highly recommend this property!"
United States
Kimberly
The price is P7,447
P8,552 total
includes taxes & fees
Oct 12 - Oct 13
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, (23 reviews)
"Great stay! Comfortable & close to a lot of stores & restaurants"
United States
Vanessa
The price is P7,447
P8,690 total
includes taxes & fees
Oct 5 - Oct 6
stayAPT Suites Hampton
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

YourSpace Hotels Chesapeake

YourSpace Hotels Chesapeake

10/10 Excellent
"Amazing! Everything clean! Convenient and practical. Definitely coming back!"
MATTEO 4-night trip
Posted 8 hours ago
YourSpace Hotels Chesapeake

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 vacation rental in Windsor?

Yes, we give you a choice of vacation rentals close to well known points of interest in Windsor, or you can select a more remote option if you'd like a relaxing place to 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 larger area, you’ll find Windsor Castle Park and Chesapeake Square Mall.

What are vacation rentals like in Windsor?

Vacation rentals are privately owned properties you can book for a couple days or more in Windsor. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for family trips or small group gatherings.