Windsor Vacations from $245

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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
Save 100% on your flight
Price was $427, price is now $245 per person
$245
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.8/10 Excellent! (1,007 reviews)

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
Price was $1,187, price is now $753 per person
$753
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9.2/10 Wonderful! (1,921 reviews)
Right on the beach.

Reviewed on Aug 3, 2026

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Save 100% on your flight
Price was $712, price is now $454 per person
$454
per person
Sep 22 - Sep 29
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.4/10 Very Good! (1,012 reviews)
This place was very welcoming to our family. Terrific staff. This was our first time in the OBX area, and they were able to recommend places to eat and were very accomodating to our family. Friendly staff. Clean room. Everything was perfect. Thank you so much!!!!

Reviewed on Aug 3, 2026

Sea Scape Beach and Golf Villas

Sea Scape Beach and Golf Villas

3.5 out of 5
Sea Scape
Save 100% on your flight
Price was $929, price is now $631 per person
$631
per person
Sep 19 - Sep 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9.4/10 Exceptional! (176 reviews)

The Barclay Towers Resort Hotel

The Barclay Towers Resort Hotel

2.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $364, price is now $257 per person
$257
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8/10 Very Good! (1,007 reviews)
When we checked in the lady behind the counter was friendly but right away I could tell that cleanliness was an issue. The lobby was dingy and not a spacious as the pictures. The floors had a smell (not a good one) the room was dingy and drab looking certainly not like the pictures. The floor was dirty. Never received cleaned towels. We went to the front desk twice and they said that they were waiting on laundry and they would send them up but we never received them. Absolutely overpriced. The only positive was the location.

Reviewed on Aug 3, 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

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
$93 nightly
The price is $110 total per night from Sep 2 to Sep 3
$110 total
Sep 2 - Sep 3
Total with taxes and fees
Wyndham Garden Norfolk Downtown
Comfort Suites Airport

Comfort Suites Airport

2.5 out of 5
12570 Jefferson Ave Newport News VA
Fully refundable
$98 nightly
The price is $113 total per night from Aug 30 to Aug 31
$113 total
Aug 30 - Aug 31
Total with taxes and fees
8.8/10 Excellent! (1,084 reviews)
"Front sleeks kept saying they didn’t work there normally and weren’t helpful."

Reviewed on Aug 4, 2026

Comfort Suites Airport
Kingsmill Resort

Kingsmill Resort

4 out of 5
1010 Kingsmill Rd Williamsburg VA
Fully refundableReserve now, pay when you stay
$218 nightly
The price is $240 total per night from Sep 1 to Sep 2
$240 total
Sep 1 - Sep 2
Total with taxes and fees
8.8/10 Excellent! (1,015 reviews)
"Great services, views, and perfect for a small getaway"

Reviewed on Aug 4, 2026

Kingsmill Resort
See all 707 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 $245 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.