Windsor Vacations from $639

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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.
Residence Inn by Marriott Greenville

Residence Inn by Marriott Greenville

3 out of 5
Price was $639, price is now $639 per person
$639
per person
May 15 - May 18
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Greenville (PGV)
8.8/10 Excellent! (493 reviews)
Wish the pool was open already. Its warm enough. Other than that it was good stay

Reviewed on Apr 6, 2026

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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
Get rates
"Country Farm House"
Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, The Inn

Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, The Inn

Merry Hill NC
$626 nightly
The price is $702 total per night from Apr 12 to Apr 13
$702 total
Apr 12 - Apr 13
Total with taxes and fees
6/10 (1 review)
Washing machine brokenMinimal kitchen untensils (no restaurants close )Was unaware the rooms are adjacent to the office area. Employees are able to walk around the living space. Each room has an individual key. This information should be shared with renters.

Reviewed on Mar 7, 2026

Luxury 4 Bedroom, Arnold Palmer Occano Coastal Club, The Inn
Quality Inn Williamston

Quality Inn Williamston

2.5 out of 5
102 East Boulevard Williamston NC
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $77 total per night from May 10 to May 11
$77 total
May 10 - May 11
Total with taxes and fees
8/10 Very Good! (507 reviews)
We were very pleased, especially with the front desk staff. Excellent!!!

Reviewed on Apr 4, 2026

Quality Inn Williamston
See all 150 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 $639 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.