
Windsor Vacations from $432
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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 $592, price is now $432 per person
$432
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


Pamlico Station Edgecamp
South Rodanthe
Save 100% on your flight
Price was $1,091, price is now $751 per person
$751
per person
Apr 15 - Apr 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9.4/10 Exceptional! (19 reviews)
beautiful room with very responsive concierge
Reviewed on Jan 15, 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 1 hour 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 8 to Feb 9
$89 total
Feb 8 - Feb 9
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
$89 nightly
The price is $105 total per night from Feb 4 to Feb 5
$105 total
Feb 4 - Feb 5
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.


















