Windsor Vacations from $982

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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.
John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
Price was $1,595, price is now $982 per person
$982
per person
Jun 17 - Jun 23
found 2 days ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9/10 Wonderful! (1,865 reviews)
Confortanke room with a great view. Centrally located.

Reviewed on Apr 9, 2026

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Save 100% on your flight
Price was $1,895, price is now $1,077 per person
$1,077
per person
Jun 17 - Jun 23
found 2 days ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,001 reviews)
It was a great visit for 1st time and hotel is at excellent location . There was no daily housekeeping services . Other than everything seems fine

Reviewed on Apr 6, 2026

Pamlico Station Edgecamp

Pamlico Station Edgecamp

2 out of 5
South Rodanthe
Save 100% on your flight
Price was $1,850, price is now $1,186 per person
$1,186
per person
Jun 17 - Jun 23
found 2 days ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9.4/10 Exceptional! (27 reviews)
We came out for our anniversary and had a wonderful time! The sauna and cold plunges were being repaired, which was disappointing, but understandable to service them in the off season. It was quiet and very relaxing and our text to the concierge was very quick!

Reviewed on Mar 30, 2026

Sanderling Resort Residences

Sanderling Resort Residences

4 out of 5
Save 100% on your flight
Price was $3,004, price is now $2,049 per person
$2,049
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip flight included
New York (NYC) to Norfolk (ORF)
No reviews
The Burrus House Inn Waterfront Suites

The Burrus House Inn Waterfront Suites

3 out of 5
Save 100% on your flight
Price was $2,373, price is now $1,623 per person
$1,623
per person
Jun 17 - Jun 23
found 2 days ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9.6/10 Exceptional! (27 reviews)
What a gorgeous property- conveniently located, close to the beaches and all types of activities. We couldn’t have been happier. Andrew and Julie G.

Reviewed on Sep 1, 2025

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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
$98 nightly
The price is $114 total per night from Apr 12 to Apr 13
$114 total
Apr 12 - Apr 13
Total with taxes and fees
8.6/10 Excellent! (1,344 reviews)
No hot water in the room A/c didn’t get cold

Reviewed on Apr 9, 2026

Embassy Suites by Hilton Hampton Convention Center
Comfort Inn & Suites Hampton near Coliseum

Comfort Inn & Suites Hampton near Coliseum

3 out of 5
1551 Hardy Cash Dr Hampton VA
Fully refundable
$89 nightly
The price is $104 total per night from Apr 22 to Apr 23
$104 total
Apr 22 - Apr 23
Total with taxes and fees
8.8/10 Excellent! (1,205 reviews)
Great place to stay. Very close to PTC for shopping and eating needs.

Reviewed on Apr 7, 2026

Comfort Inn & Suites Hampton near Coliseum
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 $158 total per night from Apr 19 to Apr 20
$158 total
Apr 19 - Apr 20
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
The M club breakfast was disappointing.

Reviewed on Apr 9, 2026

Norfolk Waterside Marriott
See all 727 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 $982 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.