
Windsor Vacations from $442
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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.

Sea Ranch Resort
Price was $602, price is now $442 per person
$442
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,001 reviews)
The room was clean, spacious, and comfortable. Privacy was respected. However, I couldn’t change the thermostat temperature lower (I guess it was locked because it was winter) as I get hot easily. The pool was nice and I liked that it was heated, but there were no towels on the racks. I wish there were showers in the pool area. I couldn’t get in the fitness center initially as the lock was broken. I did not eat at the restaurant.
Reviewed on Jan 30, 2026



Budget Inn Norfolk Va
Willoughby Spit
Save 100% on your flight
Price was $1,664, price is now $1,207 per person
$1,207
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
5.8/10 (369 reviews)
Management guarantees safety thats most important. There are plenty of restaurants around to choose from. The beach view is beautiful, and the walk to the beach is not gar at all. I enjoy being here. Im from a different state.
Reviewed on Jan 5, 2026

The Sanderling
Save 100% on your flight
Price was $1,230, price is now $902 per person
$902
per person
Mar 8 - Mar 13
found 18 hours ago
Roundtrip flight included
Chicago (ORD) to Norfolk (ORF)
8.8/10 Excellent! (523 reviews)
The elevator was broken. We were told that had been struck by lightning. I was also told that it had been broken for one year. They have three floors almost 2 of the buildings and I think two on the other, but I don’t know if they meant elevators in the building that we were in or every single one wasn’t clarified also told that they were having a New Year’s Eve celebration. Nothing was held in the lobby as previously expected the restaurant on site closed at 9 PM New Year’s Eve and we were rushed like you wouldn’t believe for six course meal that cost $300.
Reviewed on Jan 7, 2026
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.
Windsor Hotel Deals

Comfort Inn Newport News - Hampton I-64
12330 Jefferson Ave Newport News VA
$77 nightly
The price is $89 total per night from Feb 9 to Feb 10
$89 total
Feb 9 - Feb 10
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
Great staff
Reviewed on Jan 18, 2026

Norfolk Waterside Marriott
235 E Main St Norfolk VA
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $129 total per night from Feb 22 to Feb 23
$129 total
Feb 22 - Feb 23
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
Perfect snd the views
Reviewed on Jan 18, 2026

Embassy Suites by Hilton Hampton Convention Center
1700 Coliseum Drive Hampton VA
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $105 total per night from Feb 8 to Feb 9
$105 total
Feb 8 - Feb 9
Total with taxes and fees
8.4/10 Very Good! (1,246 reviews)
Elegante y personal muy amable
Reviewed on Jan 30, 2026
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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