Windsor Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to SAR 390 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Find the Best Windsor Vacation Packages

Windsor Hotel Deals

Embassy Suites by Hilton Hampton Convention Center
Embassy Suites by Hilton Hampton Convention Center
3.5 out of 5
1700 Coliseum Drive, Hampton, VA
Fully refundableReserve now, pay when you stay
The price is SAR 316 per night from Apr 27 to Apr 28
SAR 316
SAR 371 total
includes taxes & fees
27 Apr - 28 Apr
8.4/10 Very Good! (1,004 reviews)
"Nice stay"

Reviewed on 15 April 2025

Embassy Suites by Hilton Hampton Convention Center
Norfolk Waterside Marriott
Norfolk Waterside Marriott
3.5 out of 5
235 E Main St, Norfolk, VA
The price is SAR 459 per night from Apr 27 to Apr 28
SAR 459
SAR 543 total
includes taxes & fees
27 Apr - 28 Apr
8.4/10 Very Good! (1,001 reviews)
"From my arrival Zaharia checked me in! She has the heart of leadership, her question to me was” how can I make your stay better?” And she did! I want to thank her for her caring and sharing, I was there for the jazz band competition, and the band from Huston Tollison was the first winner, my reason ..."

Reviewed on 17 April 2025

Norfolk Waterside Marriott
Sheraton Norfolk Waterside Hotel
Sheraton Norfolk Waterside Hotel
3.5 out of 5
777 Waterside Dr, Norfolk, VA
Fully refundableReserve now, pay when you stay
The price is SAR 447 per night from May 5 to May 6
SAR 447
SAR 526 total
includes taxes & fees
5 May - 6 May
7.8/10 Good! (1,000 reviews)
"Front desk girls were very friendly and helpful!! Will be back very soon!"

Reviewed on 11 April 2025

Sheraton Norfolk Waterside Hotel
See all 685 properties in Windsor
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.

Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals on Expedia, you’ll be thrilled with how little a vacation to Windsor costs! Expedia’s packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Windsor?
You can typically find lower prices and better availability in January, February and November. Explore our cheap Windsor vacation packages and you could score some excellent off-season deals.
How to find the best Windsor package deals?
Begin your search for a Windsor package deal by entering your preferred travel dates and destination under our “Packages” tab. Then apply some filters, like “Property type” and “Guest rating,” to tailor the results to your exact style. You can also sort by “Package discount” and discover offers that come with huge savings. If you don’t find the ideal Windsor package deal straight away, simply play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Windsor adventure off to a flying start.
Is it cheaper to book a Windsor vacation as a package?
You can enjoy significant savings on your Windsor retreat by booking a tailored vacation package. Check the “Package” heading, then select your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Windsor?
Enjoy incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Windsor trip.
How to plan a trip to Windsor?

  1. Choose when to go: Check your schedule and get packing. Your preferred season and the type of activities on offer will also help you decide when to escape to Windsor.
  2. Budget wisely: Besides the cost of your hotel, you should consider other expenses. These include transportation, food and flights. Also, set aside a little extra for unexpected expenses that could arise during your trip to Windsor.
  3. Decide your trip length: Think about how much time you’d like to spend exploring Windsor. Plan your itinerary so you can get to all the attractions and experiences you’re interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalized Windsor vacation package.

Discover the most popular places to visit in Windsor

Boykin's Tavern

You can study the exhibits at Boykin's Tavern, a museum with a storied past, during your trip to Isle of Wight. Discover the area's live music and churches.

Boykin's Tavern