Windsor Vacations from $257

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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 $421, price is now $257 per person
$257
per person
Sep 29 - Oct 3
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.8/10 Excellent! (1,007 reviews)
I really enjoyed my stay me and my family. The 2 televisions were extremely out dated but everything else was okay...

Reviewed on Jul 21, 2026

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
Price was $588, price is now $362 per person
$362
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
9.2/10 Wonderful! (1,938 reviews)
My family’s favorite stay at OBX!

Reviewed on Jul 22, 2026

The Atrium Resort, Virginia Beach by Vacatia

The Atrium Resort, Virginia Beach by Vacatia

3.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $549, price is now $366 per person
$366
per person
Aug 28 - Aug 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.2/10 Very Good! (1,549 reviews)
The bathroom was really clean. A high rating for that. One negative to the bathroom was that the shower curtain had stains on it. The bed was comfortable. High rating for that. Negative to the bedroom was that the pillow cover had stains on it. The wall of the bedroom had dust particles building on it. The carpet to the whole unit had stains on it. One overall negative was that the entire place smelled of nuked fish throughout the stay. The smell wouldn't go away. Overall, the place is good/great to stay at. Kitchen items were provided. Clean bathroom. Comfortable bed.

Reviewed on Jul 22, 2026

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Save 100% on your flight
Price was $416, price is now $283 per person
$283
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.6/10 Excellent! (1,001 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 $987, price is now $709 per person
$709
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.2/10 Very Good! (1,337 reviews)

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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
$98 nightly
The price is $114 total per night from Aug 16 to Aug 17
$114 total
Aug 16 - Aug 17
Total with taxes and fees
Comfort Suites Airport
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
$91 nightly
The price is $111 total per night from Aug 9 to Aug 10
$111 total
Aug 9 - Aug 10
Total with taxes and fees
7/10 Good! (1,021 reviews)
"This hotel needs to close and remodel everything. It is tired and old. Everything looks rundown. The rooms are basic. The bathroom was in desperate need of remodeling (broken tile, old shower curtain, plastic covering walls). I never would have stayed here if there was something else available. Definitely ..."

Reviewed on Jul 22, 2026

Wyndham Garden Norfolk Downtown
The Landing at Hampton Marina, Tapestry Collection by Hilton

The Landing at Hampton Marina, Tapestry Collection by Hilton

3.5 out of 5
700 Settlers Landing Rd. Hampton VA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $145 total per night from Aug 11 to Aug 12
$145 total
Aug 11 - Aug 12
Total with taxes and fees
The Landing at Hampton Marina, Tapestry Collection by Hilton
See all 710 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 $257 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.