Windsor Vacations from $310

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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 $544, price is now $310 per person
$310
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Norfolk (ORF)
8.6/10 Excellent! (1,003 reviews)
The view was all worth it!!! The room was ok, but had to request towels as none in the room. Did not give any directions at check-in as far as where anything was. The tvs were both terrible with lines in both. Checkout was great, they gave me door key as we were still parking there and just spending some time on the beach.

Reviewed on Feb 22, 2026

The Sanderling

The Sanderling

4 out of 5
Save 100% on your flight
Price was $2,439, price is now $1,550 per person
$1,550
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.8/10 Excellent! (523 reviews)
The elevator was broken. We were told that had been struck by lightning. I was also told that it had been broken for one year. They have three floors almost 2 of the buildings and I think two on the other, but I don’t know if they meant elevators in the building that we were in or every single one wasn’t clarified also told that they were having a New Year’s Eve celebration. Nothing was held in the lobby as previously expected the restaurant on site closed at 9 PM New Year’s Eve and we were rushed like you wouldn’t believe for six course meal that cost $300.

Reviewed on Jan 7, 2026

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Save 100% on your flight
Price was $945, price is now $620 per person
$620
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,001 reviews)
Friendly staff. Great balcony ocean view. Cozy room.

Reviewed on Feb 20, 2026

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
Price was $951, price is now $626 per person
$626
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Norfolk (ORF)
9/10 Wonderful! (1,793 reviews)
Nice room! Loved the direct access to the beach.

Reviewed on Feb 20, 2026

The Burrus House Inn Waterfront Suites

The Burrus House Inn Waterfront Suites

3 out of 5
Save 100% on your flight
Price was $2,312, price is now $1,583 per person
$1,583
per person
Apr 11 - Apr 18
found 1 day 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

Hyatt Place Hampton Convention Center

Hyatt Place Hampton Convention Center

3 out of 5
1905 Coliseum Dr Hampton VA
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $119 total per night from Mar 1 to Mar 2
$119 total
Mar 1 - Mar 2
Total with taxes and fees
8.8/10 Excellent! (1,341 reviews)
Bathroom and room

Reviewed on Feb 18, 2026

Hyatt Place Hampton Convention Center
Norfolk Waterside Marriott

Norfolk Waterside Marriott

3.5 out of 5
235 E Main St Norfolk VA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Mar 8 to Mar 9
$149 total
Mar 8 - Mar 9
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
Nice room

Reviewed on Feb 19, 2026

Norfolk Waterside Marriott
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 Mar 1 to Mar 2
$110 total
Mar 1 - Mar 2
Total with taxes and fees
6.6/10 (1,008 reviews)
I loved the hotel. The hallways were a little chilly as it is being remolded. But beautiful and the location is ideal.

Reviewed on Feb 18, 2026

Wyndham Garden Norfolk Downtown
See all 720 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 $310 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.