
Windsor Vacations from $310
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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.

Boardwalk Resort and Villas
Northeast Virginia Beach
Save 100% on your flight
Price was $544, price is now $310 per person
$310
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.6/10 Excellent! (1,003 reviews)
The view was all worth it!!! The room was ok, but had to request towels as none in the room. Did not give any directions at check-in as far as where anything was. The tvs were both terrible with lines in both.
Checkout was great, they gave me door key as we were still parking there and just spending some time on the beach.
Reviewed on Feb 22, 2026

The Sanderling
Save 100% on your flight
Price was $2,439, price is now $1,550 per person
$1,550
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip flight included
Boston (BOS) 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



The Burrus House Inn Waterfront Suites
Save 100% on your flight
Price was $2,312, price is now $1,583 per person
$1,583
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9.6/10 Exceptional! (27 reviews)
What a gorgeous property- conveniently located, close to the beaches and all types of activities. We couldn’t have been happier.
Andrew and Julie G.
Reviewed on Sep 1, 2025
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

Hyatt Place Hampton Convention Center
1905 Coliseum Dr Hampton VA
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $119 total per night from Mar 1 to Mar 2
$119 total
Mar 1 - Mar 2
Total with taxes and fees
8.8/10 Excellent! (1,341 reviews)
Bathroom and room
Reviewed on Feb 18, 2026

Norfolk Waterside Marriott
235 E Main St Norfolk VA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Mar 8 to Mar 9
$149 total
Mar 8 - Mar 9
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
Nice room
Reviewed on Feb 19, 2026

Wyndham Garden Norfolk Downtown
700 Monticello Avenue Norfolk VA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $110 total per night from Mar 1 to Mar 2
$110 total
Mar 1 - Mar 2
Total with taxes and fees
6.6/10 (1,008 reviews)
I loved the hotel. The hallways were a little chilly as it is being remolded. But beautiful and the location is ideal.
Reviewed on Feb 18, 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.




















