Windsor Vacations from $418

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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.
Washington Motel By OYO

Washington Motel By OYO

2.5 out of 5
Price was $442, price is now $418 per person
$418
per person
Mar 14 - Mar 16
found 3 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Greenville (PGV)
4/10 (16 reviews)
Little Inn on Main

Little Inn on Main

3 out of 5
Price was $565, price is now $506 per person
$506
per person
Mar 14 - Mar 16
found 3 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Greenville (PGV)
9.8/10 Exceptional! (72 reviews)
Cutest place - was very happy when we opened the door to our room. Everything spotless, room was as described. Location was excellent! Would recommend and we will stay here again since we have family close by!

Reviewed on Dec 19, 2025

Fairfield Inn & Suites by Marriott Greenville

Fairfield Inn & Suites by Marriott Greenville

2.5 out of 5
Price was $513, price is now $491 per person
$491
per person
Mar 14 - Mar 16
found 3 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Greenville (PGV)
8.6/10 Excellent! (450 reviews)
Very nice. Would suggest something non slip in shower floor. Very slippery

Reviewed on Dec 1, 2025

Holiday Inn Express Greenville by IHG

Holiday Inn Express Greenville by IHG

2.5 out of 5
Price was $521, price is now $503 per person
$503
per person
Mar 14 - Mar 16
found 3 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Greenville (PGV)
8.4/10 Very Good! (960 reviews)
Shower and sink were not in good working order

Reviewed on Nov 6, 2025

Holiday Inn Greenville by IHG

Holiday Inn Greenville by IHG

3 out of 5
Convention District
Price was $505, price is now $489 per person
$489
per person
Mar 14 - Mar 16
found 3 hours ago
Roundtrip non-stop flight included
Houston (HOU) to Greenville (PGV)
8.8/10 Excellent! (1,000 reviews)
The front desk lady was so nice and helped my parents out when my mom became ill. Everyone was friendly and the hotel was well kept and decorated for the holidays.

Reviewed on Dec 22, 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 NC
10/10 Exceptional! (26 reviews)
Great place, peaceful

Reviewed on Sep 28, 2025

Get rates
"Country Farm House"
Golfing Paradise, Arnold Palmer Signature Golf, Luxury 4 Bedroom, Villa 116

Golfing Paradise, Arnold Palmer Signature Golf, Luxury 4 Bedroom, Villa 116

Merry Hill NC
$480 nightly
The price is $535 total per night from Jan 4 to Jan 5
$535 total
Jan 4 - Jan 5
Total with taxes and fees
Golfing Paradise, Arnold Palmer Signature Golf, Luxury 4 Bedroom, Villa 116
The Capehart - Arnold Palmer Signature Golf Community, Luxury 4 BD

The Capehart - Arnold Palmer Signature Golf Community, Luxury 4 BD

Merry Hill NC
$566 nightly
The price is $635 total per night from Jan 4 to Jan 5
$635 total
Jan 4 - Jan 5
Total with taxes and fees
The Capehart - Arnold Palmer Signature Golf Community, Luxury 4 BD
See all 148 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 $418 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.