Windsor Vacations from $545
Book a Hotel + Flight or Car together to unlock savings
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.
Williamston Inn NC Near Greenville US 64
$545
per person
Nov 12 - Nov 15
found 5 hours ago
Roundtrip non-stop flight included
New York (NYC) to Greenville (PGV)
7.8/10 Good! (31 reviews)
Rooms have been newly renovated.. very clean new fixtures. Staff was very friendly and accommodating. They have done a very nice job at renovatthr property..
Reviewed on Aug 14, 2026
Little Inn on Main
$735
per person
Nov 12 - Nov 15
found 5 hours ago
Roundtrip non-stop flight included
New York (NYC) to Greenville (PGV)
9.8/10 Exceptional! (103 reviews)
What a wonderful place to stay! Clean, quiet, everything we could ask for. Convenient parking, very friendly staff, and located on the same street where downtown Little Washington shops and restaurants are located. Can't wait to stay again!
Reviewed on Aug 16, 2026
Microtel Inn & Suites by Wyndham Greenville/University Medic
$594
per person
Nov 12 - Nov 15
found 5 hours ago
Roundtrip non-stop flight included
New York (NYC) to Greenville (PGV)
7/10 Good! (1,018 reviews)
The facility is seriously rundown and not maintained. Neither the tv or the microwave in the room were in working order and the staff would not/could not assist.
Will definitely never stay there again...
Reviewed on Sep 1, 2026
Stay near popular Windsor attractions
Historic Hope Plantation
Step back in time at Hope Plantation, where Governor Stone's 1803 mansion reveals coastal Carolina's planter elite lifestyle. Tour period-furnished rooms and explore the 1763 King-Bazemore House.
Windsor Hotel Deals
"Country Farm House"
Windsor NC
10/10 Exceptional! (32 reviews)
"Everything was perfect."
Reviewed on Jul 31, 2026
Quality Inn Williamston
102 East Boulevard Williamston NC
Fully refundable
$77 nightly
$88 total
Sep 9 - Sep 10
Total with taxes and fees
8/10 Very Good! (558 reviews)
"The staff was pleasant and helpful. The weight machine in the gym was broken. no mats to stretch on. The place was rated about what it is. We slept well and we were on our way. Thank you!"
Reviewed on Aug 28, 2026
Holiday Inn Express Williamston by IHG
1071 Cantle Court Williamston NC
Fully refundable
$93 nightly
$105 total
Sep 7 - Sep 8
Total with taxes and fees
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 |
Population | 3,800 |
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Frequently asked questions
How much does a Windsor vacation package cost?
Offering great value package deals from $545 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.