Windsor Vacations from $494

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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 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 $779, price is now $494 per person
$494
per person
Apr 29 - May 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9.2/10 Wonderful! (148 reviews)
Clean room and easy check-in/check-out

Reviewed on Dec 27, 2025

Pamlico Station Edgecamp

Pamlico Station Edgecamp

2 out of 5
South Rodanthe
Save 100% on your flight
Price was $1,306, price is now $798 per person
$798
per person
Apr 29 - May 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9.4/10 Exceptional! (24 reviews)
This hotel was fabulous. Staff were super friendly and made pre-check in so easy, and were very quick to respond to any questions. Everything was so clean, thoughtful, and welcoming. Amenities were amazing, relaxing and clean. Kitchen was fully equipped with everything you need and very clean.

Reviewed on Mar 18, 2026

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Save 100% on your flight
Price was $920, price is now $594 per person
$594
per person
May 30 - Jun 5
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,000 reviews)
Place was fabulous really enjoyed

Reviewed on Mar 22, 2026

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
Price was $1,030, price is now $690 per person
$690
per person
Apr 29 - May 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9/10 Wonderful! (1,868 reviews)
The hotel is in the middle of renovations, so there’s that. Great location and check in staff was friendly. For the price we paid for an oceanfront room, the room was ok. It had been updated, but there were cigarette ashes on our balcony and hair all over our room floor. The bathroom ceiling had mold. The neighbors that stayed near us Saturday night were obnoxiously loud til 4:30am, but that’s not the hotels fault.

Reviewed on Mar 22, 2026

Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
Price was $6,037, price is now $4,140 per person
$4,140
per person
May 30 - Jun 5
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
No reviews
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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

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
$89 nightly
The price is $105 total per night from Mar 29 to Mar 30
$105 total
Mar 29 - Mar 30
Total with taxes and fees
8.6/10 Excellent! (1,309 reviews)
Not wasting my time.

Reviewed on Mar 26, 2026

Embassy Suites by Hilton Hampton Convention Center
Sheraton Norfolk Waterside Hotel

Sheraton Norfolk Waterside Hotel

3.5 out of 5
777 Waterside Dr Norfolk VA
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $145 total per night from Mar 29 to Mar 30
$145 total
Mar 29 - Mar 30
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
The young house keeper was the best on the 5th floor

Reviewed on Mar 25, 2026

Sheraton Norfolk Waterside Hotel
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 Apr 8 to Apr 9
$110 total
Apr 8 - Apr 9
Total with taxes and fees
6.8/10 (1,001 reviews)
Staff was rushing and communication was poor. Even though it was refunded I was charged for something I without knowing the amount nor that it was charge. Wasn’t aware i had to purchase a parking pass and I also had to ask the price of that because she just swiped my card for it. Not only that the ...

Reviewed on Mar 26, 2026

Wyndham Garden Norfolk Downtown
See all 712 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 $494 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.