Windsor Vacations from $683

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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.
OYO Hotel Williamston

OYO Hotel Williamston

2 out of 5
Price was $771, price is now $683 per person
$683
per person
Dec 21 - Dec 28
found 14 hours ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Greenville (PGV)
5.8/10 (205 reviews)
Great place to bring the wife to play with other couples

Reviewed on Nov 7, 2026

Charming Single-Family Home

Charming Single-Family Home

2 out of 5
Price was $1,387, price is now $1,206 per person
$1,206
per person
Dec 21 - Dec 28
found 14 hours ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Greenville (PGV)
No reviews
Fair priced and did the job

Reviewed on Nov 1, 2026

Williamston Inn NC Near Greenville US 64

Williamston Inn NC Near Greenville US 64

2 out of 5
Price was $819, price is now $719 per person
$719
per person
Dec 21 - Dec 28
found 14 hours ago
Roundtrip non-stop flight included
Grand Rapids (GRR) to Greenville (PGV)
7.8/10 Good! (32 reviews)

Knights Inn Greenville, NC

Knights Inn Greenville, NC

2 out of 5
Price was $815, price is now $808 per person
$808
per person
Dec 24 - Dec 27
found 6 hours ago
Roundtrip non-stop flight included
White Plains (HPN) to Greenville (PGV)
4.8/10 (436 reviews)
Terrible room don’t stay

Reviewed on Nov 12, 2026

Best Western Plus Suites-Greenville

Best Western Plus Suites-Greenville

2.5 out of 5
Price was $897, price is now $895 per person
$895
per person
Dec 24 - Dec 27
found 6 hours ago
Roundtrip non-stop flight included
White Plains (HPN) to Greenville (PGV)
9/10 Wonderful! (1,007 reviews)

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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.
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Windsor Hotel Deals

"Country Farm House"

"Country Farm House"

Windsor NC
10/10 Exceptional! (34 reviews)
"The property is older as stated but a nice clean quiet place dog friendly. We enjoyed our stay and would stay here again. Nice yard and front porch. The yard is not fenced Host was responsive to questions."

Reviewed on Sep 22, 2026

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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 NC
10/10 Exceptional! (10 reviews)
"Stayed at this cute place for the third year in a row. Nice and relaxing."

Reviewed on Oct 21, 2025

Get rates
A remote getaway ... Enjoy nature, have fun and embrace relaxation!
Hampton Inn Williamston

Hampton Inn Williamston

2.5 out of 5
1099 Hampton Ct Williamston NC
$91 nightly
The price is $103 total per night from Dec 6 to Dec 7
$103 total
Dec 6 - Dec 7
Total with taxes and fees
Hampton Inn Williamston
See all 129 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
Population
3,800

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Frequently asked questions

How much does a Windsor vacation package cost?
Offering great value package deals from $683 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.