Windsor Vacation Rentals

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Check prices for these dates

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Windsor vacation rentals

Apartment | 2 bedrooms
Ice Ice Baby Downtown Newport News

Apartment in Downtown Newport News

Ice Ice Baby Downtown Newport News
2.0 star property
10.0 out of 10, Exceptional, (2)
"Loved the place.. clean and quiet!! Perfect for a weekend getaway "
United States
Nicole
Ice Ice Baby Downtown Newport News
House (4 Bedrooms) | Interior
Centrally Located Hampton Roads Home w/ Game Room!

Cottage in Portsmouth

Centrally Located Hampton Roads Home w/ Game Room!
3.0 star property
The price is NT$8,267
NT$19,441 total
includes taxes & fees
Dec 30 - Dec 31
Centrally Located Hampton Roads Home w/ Game Room!
Apartment | 2 bedrooms
The Speakeasy Downtown Newport News

Apartment in Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
The price is NT$2,839
NT$7,592 total
includes taxes & fees
Jan 10 - 2026/1/11
The Speakeasy Downtown Newport News
Terrace/patio
stayAPT Suites Suffolk-Chesapeake

Aparthotel in Suffolk

stayAPT Suites Suffolk-Chesapeake
2.5 star property
9.4 out of 10, Exceptional, (58)
"The staff was so friendly. The rooms were so nice. I loved the kitchen and breakfast bar."
United States
Nicole
The price is NT$3,741
NT$4,296 total
includes taxes & fees
Dec 30 - Dec 31
stayAPT Suites Suffolk-Chesapeake
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

Embassy Suites by Hilton Hampton Convention Center

Embassy Suites by Hilton Hampton Convention Center

10/10 Excellent
"Very good experience all around"
patrice 1-night trip
Posted 20 hours ago
Embassy Suites by Hilton Hampton Convention Center

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 Suffolk Seaboard Station Railroad Museum and St. Luke's Church.

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.