Windsor Vacations from $462

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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.
Ramada Plaza by Wyndham Nags Head Oceanfront

Ramada Plaza by Wyndham Nags Head Oceanfront

3 out of 5
Save 100% on your flight
per person
Sep 12 - Sep 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.2/10 Very Good! (1,011 reviews)
Rooms need major upgrades. Door to the balcony very hard to open. Carpet in the room looked filthy. Balcony dirty and old. Bathroom upgrade needed also.

Reviewed on Jul 30, 2025

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
per person
Sep 12 - Sep 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
9/10 Wonderful! (1,775 reviews)
Our patio door didn’t lock. Our room was not as clean as we would have liked it was around a 7 out of 10

Reviewed on Jul 31, 2025

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Save 100% on your flight
per person
Sep 12 - Sep 17
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.6/10 Excellent! (1,001 reviews)
Very quiet relaxing atmosphere.

Reviewed on Jul 27, 2025

Four Sails Resort

Four Sails Resort

3.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
7.6/10 Good! (36 reviews)
Property could use a bit of power washing and some paint. Update to memory foam beds, update the appliances and it will be perfect.

Reviewed on May 5, 2025

The Sanderling

The Sanderling

4 out of 5
Save 100% on your flight
per person
Sep 12 - Sep 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.8/10 Excellent! (496 reviews)
Great stay and clean rooms. The building exterior needs repair. The pool was awesome and not crowded. Great pool service also. Definitely would stay again.

Reviewed on Jul 24, 2025

Don't see what you're looking for?
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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

Norfolk Waterside Marriott

Norfolk Waterside Marriott

3.5 out of 5
235 E Main St, Norfolk, VA
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $159 total per night from Sep 1 to Sep 2
$159 total
Sep 1 - Sep 2
Total includes taxes and fees
8.6/10 Excellent! (1,005 reviews)
"Pretty outdated, smelly elevator"

Reviewed on Aug 1, 2025

Norfolk Waterside Marriott
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
$110 nightly
The price is $128 total per night from Aug 10 to Aug 11
$128 total
Aug 10 - Aug 11
Total includes taxes and fees
8/10 Very Good! (1,002 reviews)
Top Tier Service
"Natasha was a great customer service rep that made the check in very quick and easy. I have no complaints"

Reviewed on Jul 31, 2025

The Landing at Hampton Marina, Tapestry Collection by Hilton
Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
1551 Hardy Cash Dr, Hampton, VA
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $107 total per night from Sep 2 to Sep 3
$107 total
Sep 2 - Sep 3
Total includes taxes and fees
8.6/10 Excellent! (879 reviews)
"The hotel was convenient to the Interstate. There was plenty of close-in parking. The staff was very friendly and helpful. The one thing which I think could be done is a better description of its location when searching for it with GPS. There are a number of Comfort Inns in the vicinity and someone ..."

Reviewed on Jul 31, 2025

Comfort Inn & Suites Hampton near Coliseum
See all 694 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.

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Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from $462 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.