Windsor Vacations from $386

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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 $450, price is now $386 per person
$386
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Greenville (PGV)
4/10 (16 reviews)
Williamston Inn

Williamston Inn

2 out of 5
Price was $497, price is now $421 per person
$421
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Greenville (PGV)
8.2/10 Very Good! (22 reviews)
The room and bathroom were clean. The room was spacious. Water pressure and temperature was great. Mattress was comfortable but the bed platform made a loud metal rumbling noise every time we got out of bed, not great for light sleepers. Check in took a long time because they had a new system that the night clerk hadn’t been trained on very well. She was very nice and apologetic about the wait, but also made a slightly snarky comment about our diesel truck running outside. The bathroom had very little vanity space to sit a makeup bag and no electrical outlets. I wound up getting ready in the bedroom area at a small table where there was another mirror and I could sit my bag. Overall a good stay for a night or two.

Reviewed on Apr 26, 2026

Little Inn on Main

Little Inn on Main

3 out of 5
Price was $706, price is now $629 per person
$629
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Greenville (PGV)
9.6/10 Exceptional! (85 reviews)
Access and parking was simple and convent. Loved being right on W Main by lots of restaurants and waterfront. Clean, comfortable room.

Reviewed on Apr 30, 2026

Super 8 by Wyndham Greenville

Super 8 by Wyndham Greenville

2 out of 5
Price was $496, price is now $443 per person
$443
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Greenville (PGV)
6.6/10 (592 reviews)
Ac Great. Left before breakfast was served

Reviewed on Apr 13, 2026

Red Roof Inn Greenville, NC

Red Roof Inn Greenville, NC

2 out of 5
Price was $454, price is now $408 per person
$408
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Greenville (PGV)
4.8/10 (270 reviews)
Upon arrival the gentleman at the front was very kind and accommodating. It was a nice room very clean My only complaint is the night desk lady who gave my boyfriend her phone number to hang out together. Kinda disrespectful but other then that very comfy!! Thank you

Reviewed on Feb 23, 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 Jun 1 to Jun 2
$702 total
Jun 1 - Jun 2
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
Luxury 3 Bedroom House, Arnold Palmer Occano Coastal Club, Villa 122

Luxury 3 Bedroom House, Arnold Palmer Occano Coastal Club, Villa 122

Windsor NC
$440 nightly
The price is $494 total per night from May 3 to May 4
$494 total
May 3 - May 4
Total with taxes and fees
Luxury 3 Bedroom House, Arnold Palmer Occano Coastal Club, Villa 122
See all 146 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 $386 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.