Windsor Vacations from $328

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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.
Beach Quarters Resort

Beach Quarters Resort

2.5 out of 5
Northeast Virginia Beach
Price was $425, price is now $328 per person
$328
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.2/10 Very Good! (1,724 reviews)
Everything was very nice.The room had everything we needed for a comfort stay.

Reviewed on Nov 1, 2025

Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was $459, price is now $334 per person
$334
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,015 reviews)
Everything was perfect

Reviewed on Oct 29, 2025

Delta Hotels by Marriott Virginia Beach Waterfront Suites

Delta Hotels by Marriott Virginia Beach Waterfront Suites

4 out of 5
Northeast Virginia Beach
Price was $479, price is now $359 per person
$359
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.4/10 Very Good! (1,414 reviews)
Room and staff were excellent

Reviewed on Nov 1, 2025

The Inn at Four Eleven York

The Inn at Four Eleven York

4 out of 5
West Freemason
Price was $885, price is now $681 per person
$681
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
10/10 Exceptional! (96 reviews)
Loved our stay at the Inn. Super comfortable bed with top quality linens. Staff was very friendly and accommodating. Convenient to all the wedding activities that we were in town for. Breakfast was delicious.

Reviewed on Oct 26, 2025

TRU by Hilton Chesapeake, VA

TRU by Hilton Chesapeake, VA

2.5 out of 5
Greenbrier East
Price was $487, price is now $377 per person
$377
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (298 reviews)
We stayed here for NSU homecoming and we enjoyed our stay . The hotel was clean and reasonably price !

Reviewed on Nov 1, 2025

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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

Windsor Hotel Deals

Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
1551 Hardy Cash Dr, Hampton, VA
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $95 total per night from Nov 9 to Nov 10
$95 total
Nov 9 - Nov 10
Total with taxes and fees
8.6/10 Excellent! (1,022 reviews)
I am glad it was “off the beaten path” from all of the other hotels for Homecoming. Because of that, it was quiet!

Reviewed on Oct 26, 2025

Comfort Inn & Suites Hampton near Coliseum
Comfort Inn Newport News - Hampton I-64

Comfort Inn Newport News - Hampton I-64

2.5 out of 5
12330 Jefferson Ave, Newport News, VA
$72 nightly
The price is $84 total per night from Dec 1 to Dec 2
$84 total
Dec 1 - Dec 2
Total with taxes and fees
8.2/10 Very Good! (1,009 reviews)
Every thing was just as expected. Perfect

Reviewed on Nov 2, 2025

Comfort Inn Newport News - Hampton I-64
Norfolk Waterside Marriott

Norfolk Waterside Marriott

3.5 out of 5
235 E Main St, Norfolk, VA
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $131 total per night from Nov 23 to Nov 24
$131 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (1,006 reviews)
Clean room, great staff, convenient parking, and breakfast was delicious.

Reviewed on Oct 27, 2025

Norfolk Waterside Marriott
See all 677 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.

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 $328 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.