Windsor Vacations from $391

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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.
The Lodge at Kiln Creek Resort

The Lodge at Kiln Creek Resort

3.5 out of 5
Central Newport News
Price was $525, price is now $391 per person
$391
per person
Nov 28 - Dec 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9/10 Wonderful! (188 reviews)
Clean, friendly staff, high quality furniture, and easy access to the building. Would stay here again!

Reviewed on Sep 8, 2025

Beach Quarters Resort

Beach Quarters Resort

2.5 out of 5
Northeast Virginia Beach
Save 100% on your flight
Price was $678, price is now $435 per person
$435
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.2/10 Very Good! (1,675 reviews)
We have always stayed here when we visit VA Beach, unfortunately this year they implemented a no cash policy. We found out AT THE PROPERTY. So we wont be staying again.

Reviewed on Sep 17, 2025

Sea Ranch Resort

Sea Ranch Resort

3 out of 5
Save 100% on your flight
Price was $610, price is now $426 per person
$426
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,006 reviews)
LovI d that it was on the beach.

Reviewed on Sep 11, 2025

John Yancey Oceanfront Inn

John Yancey Oceanfront Inn

2 out of 5
Save 100% on your flight
Price was $566, price is now $397 per person
$397
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
9/10 Wonderful! (1,735 reviews)
What I liked:The check in staff was very pleasant and personable, the bed and pillows were comfortable, room was clean. What I didn't like: Room, bathroom, stairwell, elevator, and hallways need fresh coat of paint as well repairing some of the woodwork. Room smelled musty. Poor shower pressure. The complementary breakfast was not good. The pictures on line made the room and facilities look MUCH better than what they are.

Reviewed on Sep 17, 2025

Boardwalk Resort and Villas

Boardwalk Resort and Villas

3 out of 5
Northeast Virginia Beach
Price was $632, price is now $478 per person
$478
per person
Oct 22 - Oct 26
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Norfolk (ORF)
8.6/10 Excellent! (1,017 reviews)
Staff was super helpful and accommodating with all of our requests and needs. Pool was great. Bed was comfortable. View was perfect. Would 100% stay here again!

Reviewed on Sep 14, 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
$96 nightly
The price is $112 total per night from Sep 25 to Sep 26
$112 total
Sep 25 - Sep 26
Total with taxes and fees
8.8/10 Excellent! (1,291 reviews)
"Staff was most kind and so accommodating. Would definitely stay here again."

Reviewed on Sep 15, 2025

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
$135 nightly
The price is $159 total per night from Oct 12 to Oct 13
$159 total
Oct 12 - Oct 13
Total with taxes and fees
8.6/10 Excellent! (1,010 reviews)
"Pillows too hard and firm for comfortable sleep. Also, temperature maintained at about 68 degrees throughout property, too cold for comfort."

Reviewed on Sep 16, 2025

Norfolk Waterside Marriott
Comfort Inn Newport News - Hampton I-64

Comfort Inn Newport News - Hampton I-64

2.5 out of 5
12330 Jefferson Ave, Newport News, VA
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $85 total per night from Sep 30 to Oct 1
$85 total
Sep 30 - Oct 1
Total with taxes and fees
8.4/10 Very Good! (1,009 reviews)
"Nice that the place is dog friendly. Our room was very clean and I would stay here again."

Reviewed on Sep 16, 2025

Comfort Inn Newport News - Hampton I-64
See all 661 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 $391 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

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.