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Windsor Vacation Rentals

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Check prices for these dates

In two weeks
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Windsor vacation rentals

Terrace/patio

stayAPT Suites Suffolk-Chesapeake

stayAPT Suites Suffolk-Chesapeake
3.5 star property
Suffolk
9.6 out of 10, Exceptional, (95 reviews)
"Perfect! Will stay again and will look for this brand in my future travels."
United States
Melissa
The price is NT$3,841
NT$4,444 total
includes taxes & fees
Aug 13 - Aug 14
stayAPT Suites Suffolk-Chesapeake
House | 2 bedrooms

Ice Ice Baby Downtown Newport News

Ice Ice Baby Downtown Newport News
2.0 star property
Downtown Newport News
7.4 out of 10, Good, (3 reviews)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
The price is NT$5,261
NT$10,437 total
includes taxes & fees
Jul 26 - Jul 27
Ice Ice Baby Downtown Newport News
House (4 Bedrooms) | Interior

Centrally Located Hampton Roads Home w/ Game Room!

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
Portsmouth
The price is NT$9,393
NT$19,982 total
includes taxes & fees
Aug 16 - Aug 17
Centrally Located Hampton Roads Home w/ Game Room!
House | 2 bedrooms

The Speakeasy Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
Downtown Newport News
The price is NT$5,216
NT$10,384 total
includes taxes & fees
Jul 27 - Jul 28
The Speakeasy Downtown Newport News
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
"Very helpful and friendly staff. The hotel is clean and we loved the complimentary wine and snacks."
Sandra 1-night trip
Posted 1 hour 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 Regal Harbour View Grande 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.