Windsor Vacations from $441

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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 $549, price is now $441 per person
$441
per person
Jan 14 - Jan 18
found 18 hours ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
8.8/10 Excellent! (1,003 reviews)

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

4 out of 5
Northeast Virginia Beach
Price was $662, price is now $541 per person
$541
per person
Jan 14 - Jan 18
found 17 hours ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
8.2/10 Very Good! (1,447 reviews)

Marriott Virginia Beach Oceanfront Resort

Marriott Virginia Beach Oceanfront Resort

4 out of 5
Northeast Virginia Beach
Price was $792, price is now $678 per person
$678
per person
Jan 14 - Jan 18
found 17 hours ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
9/10 Wonderful! (1,001 reviews)
Awesome beach view

Reviewed on Nov 3, 2026

The Barclay Towers Resort Hotel

The Barclay Towers Resort Hotel

2.5 out of 5
Northeast Virginia Beach
Price was $605, price is now $521 per person
$521
per person
Jan 14 - Jan 18
found 17 hours ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
7.8/10 Good! (1,002 reviews)
Cool stay. Staff was very cool.

Reviewed on Nov 2, 2026

Fairfield Inn & Suites by Marriott Virginia Beach Oceanfront

Fairfield Inn & Suites by Marriott Virginia Beach Oceanfront

3 out of 5
Northeast Virginia Beach
Price was $646, price is now $564 per person
$564
per person
Jan 14 - Jan 18
found 17 hours ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
8.6/10 Excellent! (1,006 reviews)
Great stay! Indoor pool & hot tub was wonderful. We stayed in a suite and loved it! Breakfast was nice. Bummed we had to pay $24 a night to park! That should have been included in cost of hotel.

Reviewed on Nov 2, 2026

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Stay near popular Windsor attractions

Boykin's Tavern

8.0/10 (1 review)
This 18th-century tavern showcases original colonial paneling and period furnishings adjacent to the historic courthouse. Explore the well-preserved rooms for an authentic glimpse into Revolutionary War-era social life.
See properties

Windsor Hotel Deals

Comfort Suites Airport

Comfort Suites Airport

2.5 out of 5
12570 Jefferson Ave Newport News VA
Fully refundable
$90 nightly
The price is $105 total per night from Nov 30 to Dec 1
$105 total
Nov 30 - Dec 1
Total with taxes and fees
Comfort Suites Airport
Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
1551 Hardy Cash Dr Hampton VA
Fully refundable
$84 nightly
The price is $98 total per night from Nov 29 to Nov 30
$98 total
Nov 29 - Nov 30
Total with taxes and fees
Comfort Inn & Suites Hampton near Coliseum
Wyndham Garden Norfolk Downtown

Wyndham Garden Norfolk Downtown

3.5 out of 5
700 Monticello Avenue Norfolk VA
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $103 total per night from Nov 15 to Nov 16
$103 total
Nov 15 - Nov 16
Total with taxes and fees
Wyndham Garden Norfolk Downtown
See all 691 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 $441 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.