Windsor Vacations from $480

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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.
Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Price was $699, price is now $480 per person
$480
per person
Sep 5 - Sep 8
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,010 reviews)
Adequate

Reviewed on Jul 2, 2026

The Ocean Key Virginia Beach Resort

The Ocean Key Virginia Beach Resort

3 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $905, price is now $641 per person
$641
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
7.6/10 Good! (1,552 reviews)
The location is pretty much all you pay for. The hotel pool was tiny and had a silky film all over the top. The hot tub was broken and no one was informed while booking that it was broken. Also, there was people screaming and strung out yelling down our hall way acting like they were fighting or murdering people. Very scary. Also, they have “guests” living there who send their children out to pan handle the guest. They ask for money or they sell stuff. Very disappointed. But it was clean and it was a cute room with a good location.

Reviewed on Jul 3, 2026

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

4 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $980, price is now $696 per person
$696
per person
Sep 12 - Sep 19
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.2/10 Very Good! (1,312 reviews)
Me encanto, buen servicio excelente ubicación ambiente familiar

Reviewed on Jul 3, 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 $823, price is now $602 per person
$602
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.2/10 Very Good! (1,530 reviews)
The room was clean and presentable. The staff were friendly and available at reception. If you wanted clean towels you could swap out at the linen dept. Room cleaning want available. Parking was available free of charge with a ticket. Enjoyable stay, swimming pool was a bonus.

Reviewed on Jul 3, 2026

Belmont Inn And Suites

Belmont Inn And Suites

2 out of 5
Northeast Virginia Beach
Price was $4,245, price is now $3,202 per person
$3,202
per person
Sep 5 - Sep 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
4.8/10 (244 reviews)
Clean Room, Helpful Staff, Shopp

Reviewed on Jun 26, 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
$100 nightly
The price is $118 total per night from Aug 2 to Aug 3
$118 total
Aug 2 - Aug 3
Total with taxes and fees
7/10 Good! (1,003 reviews)
"This was the loudest property I have ever stayed in. Be aware if you want a good nights sleep that the walls are paper thin."

Reviewed on Jul 1, 2026

Wyndham Garden Norfolk Downtown
Comfort Suites Airport

Comfort Suites Airport

2.5 out of 5
12570 Jefferson Ave Newport News VA
Fully refundable
$101 nightly
The price is $117 total per night from Jul 26 to Jul 27
$117 total
Jul 26 - Jul 27
Total with taxes and fees
8.8/10 Excellent! (1,019 reviews)
"We had a great stay! Comfy beds, very accommodating staff and great breakfast."

Reviewed on Jul 4, 2026

Comfort Suites Airport
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
$98 nightly
The price is $114 total per night from Aug 2 to Aug 3
$114 total
Aug 2 - Aug 3
Total with taxes and fees
8.6/10 Excellent! (1,511 reviews)
"Very nice place enjoyed my 4day stay"

Reviewed on Jul 4, 2026

Embassy Suites by Hilton Hampton Convention Center
See all 716 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 $480 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.