Windsor Vacation Rentals

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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Windsor holiday rentals

Property grounds
Mariners Cove 4 Bedroom Cottage by RedAwning

Cottage in Willoughby Spit

Mariners Cove 4 Bedroom Cottage by RedAwning
3.0 star property
8.0 out of 10, Very good, (1)
"Great location right on the water with lots of space inside and out. The host was very helpful and easy to work with. "
United States
Arvind
The price is RM598
RM1,856 total
includes taxes & fees
21 Dec - 22 Dec
Mariners Cove 4 Bedroom Cottage by RedAwning
2 bedrooms
The Speakeasy Downtown Newport News

Apartment in Downtown Newport News

The Speakeasy Downtown Newport News
2.0 star property
The price is RM389
RM1,014 total
includes taxes & fees
21 Dec - 22 Dec
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, (55)
"The staff was so friendly. The rooms were so nice. I loved the kitchen and breakfast bar."
United States
Nicole
The price is RM486
RM558 total
includes taxes & fees
18 Dec - 19 Dec
stayAPT Suites Suffolk-Chesapeake
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 RM1,189
RM2,658 total
includes taxes & fees
31 Dec - 1 Jan 2026
Centrally Located Hampton Roads Home w/ Game Room!
2 bedrooms
Breakfast Tiffany s Downtown Newport News

Apartment in Downtown Newport News

Breakfast Tiffany s Downtown Newport News
2.0 star property
6.0 out of 10, (1)
"The property was nice but full of insects my kids didn’t want to sleep there. "
United States
James
The price is RM320
RM922 total
includes taxes & fees
21 Dec - 22 Dec
Breakfast Tiffany s Downtown Newport News
1 bedroom
The Safe House Downtown Newport News

Apartment in Downtown Newport News

The Safe House Downtown Newport News
2.0 star property
6.0 out of 10, (1)
The price is RM375
RM995 total
includes taxes & fees
18 Dec - 19 Dec
The Safe House 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

Sonesta Simply Suites Hampton

Sonesta Simply Suites Hampton

10/10 Excellent
"Everything was good"
Jackie 21-night trip
Posted 2 days ago
Sonesta Simply Suites Hampton

Find out more about Windsor

Search for holiday rentals in Windsor on Expedia.co.uk! 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 Suffolk Seaboard Station Railroad Museum 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.