Windsor Vacations from $628

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Your Windsor Vacation

With a vacation package to Windsor, say goodbye to endless planning and hello to trouble-free adventure. Every detail of your escape has been taken care of before departing, so you can make the most of your time discovering this awesome city. During your trip to Windsor, set aside some time for sightseeing. One of the best places to start exploring is Historic Hope Plantation. Check out Expedia's extensive range of travel options and start planning your dream vacation to Windsor today.

The Latest Windsor vacation packages

Price found within the past 48 hours. Click for updated prices.
Homewood Suites By Hilton Greenville, NC

Homewood Suites By Hilton Greenville, NC

3 out of 5
per person
Sep 24 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Greenville (PGV)
9.4/10 Exceptional! (262 reviews)
I liked the cleanliness of the entire hotel. The staff were very polite and professional. I also appreciated the amenities and convenience of the room to comfortably fit my family. We were in town for a funeral and Homewood suites made us feel comfortable and treated us like family.

Reviewed on Aug 10, 2025

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Discover the most popular places to visit in Windsor

Historic Hope Plantation

You can learn about the history of Windsor with a visit to Historic Hope Plantation. Make some time to visit the monuments while you're in the area.

Historic Hope Plantation

Windsor Hotel Deals

"Country Farm House"

"Country Farm House"

Windsor
10/10 Exceptional! (23 reviews)
Serenity in Windsor
"My family needed a place to stay for Memorial Day weekend. It worked out much better than a hotel. The beds were comfortable. It was as advertised. An old farm house that brought back many memories. Will definitely stay again if the need arises."

Reviewed on May 29, 2025

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"Country Farm House"
A remote getaway ... Enjoy nature, have fun and embrace relaxation!

A remote getaway ... Enjoy nature, have fun and embrace relaxation!

windsor
Hunting Trip
"The Legacy Lodge was cozy and convenient. We enjoy staying there."

Reviewed on Oct 19, 2024

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A remote getaway ... Enjoy nature, have fun and embrace relaxation!
Americas Best Value Inn Edenton

Americas Best Value Inn Edenton

2 out of 5
501 Virginia Rd, Us-17 Bypass & Rt.32 Exit#227, Edenton, NC
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $101 total per night from Aug 13 to Aug 14
$101 total
Aug 13 - Aug 14
Total includes taxes and fees
6/10 (371 reviews)
"This is an older property. Not bad for the price. Generally positive. Some gripes. Small bathroom, poor TV quality."

Reviewed on Jul 23, 2025

Americas Best Value Inn Edenton
See all 130 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 $628 on Expedia, you'll be pleasantly surprised at how much a vacation to Windsor costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Windsor?
If you'd like to book a cheap Windsor vacation package, consider visiting in November, December and January. You'll usually find better rates on flights and accommodations during these quieter months — ideal for a budget-friendly break.
How many days is enough for Windsor?
Usually, a handful of days is enough to check out the top sights during your Windsor vacation. However, if you want to have some time to kick back or go on day trips, consider extending your trip.
How to find the best Windsor package deals?
Bagging a cheap Windsor package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Windsor package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Windsor vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and accommodations individually. Better still, you can tailor your Windsor escape to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Windsor?
If you're planning a spur-of-the-moment Windsor adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Windsor vacation packages?
Secure your dream getaway to Windsor with Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait until your next payday — we've partnered with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to budget for your trip and snap up travel deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.