Greenwood Vacations from $696

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The Latest Greenwood vacation packages

Price found within the past 48 hours. Click for updated prices.
The Surf Shanty Motel

The Surf Shanty Motel

2.5 out of 5
Save 100% on your flight
Price was $918, price is now $696 per person
$696
per person
Jul 13 - Jul 17
found 10 hours ago
Roundtrip flight included
New York (LGA) to Salisbury (SBY)
9.8/10 Exceptional! (319 reviews)
Wonderful place ocean block …

Reviewed on May 18, 2026

Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $1,707, price is now $1,221 per person
$1,221
per person
Jul 4 - Jul 11
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
8/10 Very Good! (31 reviews)
The unit was outdated, small, and had mismatched and old furniture. The shower in one of our bathrooms wouldn’t drain. The oven did not work. There was only one television. Concerns couldn’t be communicated because the staff hardly spoke English (although they were very nice). The unit was in a really nice location - 1.5 blocks from the boardwalk and beach. We liked the outside showers.

Reviewed on Aug 9, 2025

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Save 100% on your flight
Price was $1,410, price is now $1,059 per person
$1,059
per person
Jul 13 - Jul 17
found 10 hours ago
Roundtrip flight included
New York (LGA) to Salisbury (SBY)
9.6/10 Exceptional! (757 reviews)
We loved loved loved the property, the staff, especially Stacey, who prepared our breakfast, The amenities were amazing. The bed and shower were extra cozy. It was super quiet. We felt relaxed, cared for, and the location was awesome for traveling to either Rehoboth or Ocean City. We will be definitely booking again. Thank you for an enjoyable and relaxing vacation!

Reviewed on May 22, 2026

The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
Price was $2,064, price is now $1,562 per person
$1,562
per person
Aug 13 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
8.6/10 Excellent! (1,196 reviews)
El hotel estaba muy limpio solo algunos detalles que se pueden arreglar como el techo del baño pero de los d3mas muy limpio y buena ubicación!!

Reviewed on May 25, 2026

Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Price was $2,026, price is now $1,562 per person
$1,562
per person
Aug 13 - Aug 19
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Salisbury (SBY)
8.2/10 Very Good! (720 reviews)
Clean room. Nice staff, great location on the boardwalk.

Reviewed on May 13, 2026

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Greenwood Hotel Deals

Luxury Treehouse with Large Deck

Luxury Treehouse with Large Deck

Harrington DE
10/10 Exceptional! (26 reviews)
"We traveled for a wedding and decided it was a wonderful opportunity to try something different. Who would book a hotel when this is available. The property was perfect such a beautiful peaceful location. It rained our entire stay but having the doors open and enjoying the sound of the trees was ..."

Reviewed on May 24, 2026

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Luxury Treehouse with Large Deck
Hyatt House Lewes/Rehoboth Beach

Hyatt House Lewes/Rehoboth Beach

3.5 out of 5
17254 Five Points Square Lewes DE
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $135 total per night from Jun 3 to Jun 4
$135 total
Jun 3 - Jun 4
Total with taxes and fees
9.4/10 Exceptional! (1,004 reviews)
"Staff is great. The breakfast is awesome. The room was spotless clean. Highly recommend."

Reviewed on May 24, 2026

Hyatt House Lewes/Rehoboth Beach
Home2 Suites by Hilton Lewes Rehoboth Beach

Home2 Suites by Hilton Lewes Rehoboth Beach

3 out of 5
17388 Ocean One Plaza Lewes DE
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $99 total per night from Jun 7 to Jun 8
$99 total
Jun 7 - Jun 8
Total with taxes and fees
9.4/10 Exceptional! (1,003 reviews)
"Clean facilities and very spacious. Good breakfast"

Reviewed on May 23, 2026

Home2 Suites by Hilton Lewes Rehoboth Beach
See all 623 properties in Greenwood
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 $696 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.