Windsor Vacations from $413

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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

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was $592, price is now $413 per person
$413
per person
May 27 - May 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,005 reviews)
We got a suite with ocean view. It was clean and the view was beautiful the next morning on the balcony.

Reviewed on Mar 14, 2026

Pamlico Station Edgecamp

Pamlico Station Edgecamp

2 out of 5
South Rodanthe
Save 100% on your flight
Price was $1,634, price is now $1,080 per person
$1,080
per person
Jun 8 - Jun 13
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
9.4/10 Exceptional! (23 reviews)
beautiful room with very responsive concierge

Reviewed on Jan 15, 2026

Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
Price was $5,333, price is now $3,563 per person
$3,563
per person
Jun 8 - Jun 13
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
No reviews
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
Price was $1,206, price is now $819 per person
$819
per person
Jun 8 - Jun 13
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
9/10 Wonderful! (1,868 reviews)
Room was the CUTEST! Bathroom was huge. One of the cleanest (like sparkling clean) places we have ever stayed. It is right on the beach with easy, easy beach access. Large beach area for hotel. Wonderful two-story, covered deck area. A two-minute walk to Swells'a brewery :). If we ever have the opportunity to return to the OBX, John Yancey is where we will stay.

Reviewed on Mar 12, 2026

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was $911, price is now $630 per person
$630
per person
Jun 8 - Jun 13
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.6/10 Excellent! (1,000 reviews)
Friendly staff. Great balcony ocean view. Cozy room.

Reviewed on Feb 20, 2026

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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

Embassy Suites by Hilton Hampton Convention Center

Embassy Suites by Hilton Hampton Convention Center

3.5 out of 5
1700 Coliseum Drive Hampton VA
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $105 total per night from Mar 22 to Mar 23
$105 total
Mar 22 - Mar 23
Total with taxes and fees
8.6/10 Excellent! (1,298 reviews)
Yes

Reviewed on Mar 14, 2026

Embassy Suites by Hilton Hampton Convention Center
Norfolk Waterside Marriott

Norfolk Waterside Marriott

3.5 out of 5
235 E Main St Norfolk VA
$135 nightly
The price is $158 total per night from Mar 23 to Mar 24
$158 total
Mar 23 - Mar 24
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
Great central location.

Reviewed on Mar 12, 2026

Norfolk Waterside Marriott
Sheraton Norfolk Waterside Hotel

Sheraton Norfolk Waterside Hotel

3.5 out of 5
777 Waterside Dr Norfolk VA
$107 nightly
The price is $126 total per night from Mar 22 to Mar 23
$126 total
Mar 22 - Mar 23
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
All was well until

Reviewed on Mar 14, 2026

Sheraton Norfolk Waterside Hotel
See all 727 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 $413 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

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