Greenwood Vacations from $655

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The Latest Greenwood vacation packages

Price found within the past 48 hours. Click for updated prices.
Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Save 100% on your flight
Price was $936, price is now $655 per person
$655
per person
Aug 3 - Aug 8
found 18 hours ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
8.8/10 Excellent! (1,008 reviews)
This was my second stay with my family and as usual 10/10! Amazingly kind staff at the front desk! We will definitely be back !

Reviewed on May 17, 2026

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Save 100% on your flight
Price was $1,751, price is now $1,113 per person
$1,113
per person
Aug 3 - Aug 8
found 18 hours ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
9.4/10 Exceptional! (753 reviews)
Clean room, great staff, nice bar

Reviewed on May 13, 2026

The Surf Shanty Motel

The Surf Shanty Motel

2.5 out of 5
Save 100% on your flight
Price was $1,199, price is now $779 per person
$779
per person
Aug 3 - Aug 8
found 18 hours ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
9.8/10 Exceptional! (317 reviews)
Wonderful place ocean block …

Reviewed on May 18, 2026

Hampton Inn & Suites Ocean City/Bayfront-Convention Center

Hampton Inn & Suites Ocean City/Bayfront-Convention Center

2.5 out of 5
Midtown Ocean City
Save 100% on your flight
Price was $1,285, price is now $862 per person
$862
per person
Aug 3 - Aug 8
found 18 hours ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
8.8/10 Excellent! (1,000 reviews)
The price was good and the stay was also good.

Reviewed on May 15, 2026

Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $1,845, price is now $1,322 per person
$1,322
per person
Jul 18 - Jul 23
found 1 hour ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
7.4/10 Good! (171 reviews)
Got better than what I expected for the price. Front desk ladies were happy & helpfully. Only thing that would be nice would be some type of dimmer lights for night, outlets near beds & softer beds. Will definately be staying here again! Full kitchen with full size fridge saved us $ not having to eat out. It's like a hotel sized condo.

Reviewed on Oct 1, 2025

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Greenwood Hotel Deals

Luxury Treehouse with Large Deck

Luxury Treehouse with Large Deck

Harrington DE
10/10 Exceptional! (24 reviews)
"What a peaceful place to stay with your love ones.i can’t say how pleasant my host was to work with.this is such a dream treehouse to stay in . I hope I will someday return here ."

Reviewed on May 7, 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
$113 nightly
The price is $125 total per night from May 25 to May 26
$125 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (1,003 reviews)
"Great place recommended to everybody very clean the food was great and the people were friendly"

Reviewed on May 17, 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
$123 nightly
The price is $137 total per night from May 28 to May 29
$137 total
May 28 - May 29
Total with taxes and fees
9.4/10 Exceptional! (1,006 reviews)
"There was amble space in the hotel room. Unfortunately, the hotel smelled of dog. I had difficulty sleeping with the noise from the room next to me. I was hoping to use the pool, but the floors were soaked & it was a small pool. Overall I didn't sleep well & felt allergic in the hotel."

Reviewed on May 17, 2026

Home2 Suites by Hilton Lewes Rehoboth Beach
See all 617 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 $655 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.