Windsor Vacations from $625
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Your Windsor Vacation
The exciting city of Windsor is calling your name. Delve into everything from its highlights to its hidden gems with a Windsor vacation package that's custom made for you. During your trip to Windsor, take all the time you need for sightseeing. A perfect place to start exploring is Lake Prince. That dream Windsor vacation is clicks away. Browse accommodations, flights and more on Expedia for a getaway that's tailored to suit your style.
The Latest Windsor vacation packages
Price found within the past 48 hours. Click for updated prices.
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Northeast Virginia Beach
$737
per person
Nov 23 - Nov 27
found 22 hours ago
Roundtrip flight included
Minneapolis (MSP) to Norfolk (ORF)
8.2/10 Very Good! (1,387 reviews)
I have to admit I’m very happy and felt so special when
Reviewed on Sep 11, 2026
The Colony at Virginia Beach
Northeast Virginia Beach
$861
per person
Nov 23 - Nov 27
found 22 hours ago
Roundtrip flight included
Minneapolis (MSP) to Norfolk (ORF)
9.6/10 Exceptional! (42 reviews)
The parking is SUPER tight and the beds are extremely firm. Not something I like so made the stay a little uncomfortable for me. The location and the staff were amazing. My kids loved the ice cream social they had! The condo was clean and fully stocked with everything we needed to cook! I would definitely consider staying here again if the beds were not so uncomfortable for me.
Reviewed on Sep 9, 2026
Stay near popular Windsor attractions
Boykin's Tavern
8.0/10 (1 review)
This 18th-century tavern showcases original colonial paneling and period furnishings adjacent to the historic courthouse. Explore the well-preserved rooms for an authentic glimpse into Revolutionary War-era social life.
Windsor Hotel Deals
Comfort Suites Airport
12570 Jefferson Ave Newport News VA
Fully refundable
$96 nightly
$111 total
Oct 11 - Oct 12
Total with taxes and fees
Kingsmill Resort
1010 Kingsmill Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
$218 nightly
$240 total
Sep 13 - Sep 14
Total with taxes and fees
Wyndham Garden Norfolk Downtown
700 Monticello Avenue Norfolk VA
Fully refundableReserve now, pay when you stay
$93 nightly
$110 total
Sep 27 - Sep 28
Total with taxes and fees
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.
Find the Best Windsor Vacation Packages
Windsor Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Newport News - Williamsburg Intl. Airport (PHF) |
Population | 2,700 |
Top Sights | Riddicks Folly House Museum, Lake Prince and Suffolk Seaboard Station Railroad Museum |
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Frequently asked questions
How much does a Windsor vacation package cost?
Offering great value package deals from $625 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?
If you're hoping to book a cheap Windsor vacation package, consider visiting in December, January and February. You'll usually find lower prices on flights and accommodations during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Windsor?
The ideal duration for your Windsor vacation depends on what you'd like to see. Generally, a few days to a week will give you enough time to visit all the leading attractions and discover some hidden spots along the way.
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.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
Jet off on your perfect escape to Windsor with Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait until payday — we've joined forces with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no hidden or late payment fees, you can easily stay on budget and snap up bargains while they last.
Explore a world of travel with Expedia
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- Visit Windsor
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- The Peanut Patch
- Waterside District
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- Windsor Castle Park
- Christopher Newport University
- Chesapeake Square Mall
- Smithfield Farmers Market
- Suffolk Seaboard Station Railroad Museum
- Smithfield Vacations
- Mariner's Museum
- Old Dominion University
- College of William and Mary
- Virginia Zoo
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- Isle of Wight Vacations
- Virginia Beach Vacations
- Suffolk Center for Cultural Arts
- Portsmouth Naval Shipyard Museum
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- Virginia Beach Boardwalk
- Children's Museum of Virginia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
