Greenwood Vacations from $984
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The Latest Greenwood vacation packages
Price found within the past 48 hours. Click for updated prices.
Boardwalk One
Downtown Ocean City
$984
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
7.4/10 Good! (174 reviews)
Room was as expected, worked well for our family. The women in the office were very kind and the check-in process was very smooth. We would stay here again.
Reviewed on Aug 3, 2026
Ocean 1 Hotel and Suites
Downtown Ocean City
$1,763
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
8.2/10 Very Good! (766 reviews)
First noticed that there was no sound proofing and could hear everything (even people talking) from street 4 floors down. Found TV cable line disconnected after front desk could not find why TV not working. There were connection issues the entire time there. Then found the bath tub did not drain. Limited towels and seemed to be an issue getting more. Coffee maker in room dirty and no coffee at front desk.
Reviewed on Aug 12, 2026
Greenwood Hotel Deals
Luxury Treehouse with Large Deck
Harrington DE
10/10 Exceptional! (39 reviews)
"This cute little treehouse was just perfect! My 19 yo daughter and I stayed and didn’t want to leave. Close to cute small towns, beaches and shopping. The small details inside the house made it so special. Plus Eddie the pup visited and welcomed us like family. We will definitely be back!!"
Reviewed on Aug 12, 2026
Hyatt House Lewes/Rehoboth Beach
17254 Five Points Square Lewes DE
Fully refundableReserve now, pay when you stay
$106 nightly
$118 total
Sep 8 - Sep 9
Total with taxes and fees
9.4/10 Exceptional! (1,028 reviews)
"Very spacious room and bathroom! Easy to navigate due to helpful staff and everything is well kept and clean."
Reviewed on Aug 13, 2026
Tru by Hilton Georgetown
301 College Park Lane Georgetown DE
Fully refundableReserve now, pay when you stay
$93 nightly
$103 total
Sep 6 - Sep 7
Total with taxes and fees
9/10 Wonderful! (606 reviews)
"Great"
Reviewed on Aug 12, 2026
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 Greenwood Vacation Packages
Greenwood Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 1,050 |
Max Temp Winter | 45ºF |
Max Temp Summer | 80ºF |
Top Sights | Second Street Players - Riverfront Theatre, The Rookery North Golf Course and Abbotts Mill Nature Center |
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Frequently asked questions
How much does a Greenwood vacation package cost?
Offering great value package deals from $984 on Expedia, you'll be thrilled with how little a vacation to Greenwood costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Greenwood?
October, November and December are great times to look for cheap Greenwood vacation packages. Opting to travel in quieter months means you can usually find lower prices on hotels and flights.
How many days is enough for Greenwood?
With a well-organized travel plan, you can easily tick off the most popular Greenwood sights in a few days. But if you want to venture off the beaten track or take day trips, consider booking your Greenwood vacation for longer.
How to find the best Greenwood package deals?
Use Expedia's filters to find some unbeatable Greenwood package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or look for Greenwood package deals in the low season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Greenwood vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Greenwood vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Greenwood?
If you have your Greenwood vacation dates confirmed, book early to snap up some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Greenwood vacation packages?
Your Greenwood getaway is meant to be a relaxing escape from your busy life, not a source of money-related stress. So to allow you extra flexibility, we've partnered with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
