Greenwood Vacations from $443

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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
Price was $584, price is now $443 per person
$443
per person
Jun 27 - Jun 29
found 1 day ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
9.8/10 Exceptional! (319 reviews)
Wonderful place ocean block …

Reviewed on May 18, 2026

Sahara Motel

Sahara Motel

2.5 out of 5
Downtown Ocean City
Price was $949, price is now $675 per person
$675
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Baltimore (BWI) to Salisbury (SBY)
7.6/10 Good! (545 reviews)
ok for a last minute stay

Reviewed on May 27, 2026

Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $1,801, price is now $1,307 per person
$1,307
per person
Jul 19 - Jul 25
found 22 hours 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

The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
Price was $1,282, price is now $1,002 per person
$1,002
per person
Aug 13 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
8.6/10 Excellent! (1,202 reviews)
The staff was amazing!!!!! From the front desk to the cleaning staff they were all so friendly and helpful. We interacted with so many of them on a daily basis & they all made our stay amazing. We want to shoutout Bre, we had a small issue that could have become bigger but she went above & beyond to remedy it immediately. Our room was fabulous! We had a king suite on the 7th floor with an ocean view & it didn’t disappoint. Very clean & spacious for the 2 of us. We loved the location & proximity to the ocean & boardwalk. Even with not great weather we loved our stay & will definitely stay here again because of the amazing staff.

Reviewed on May 27, 2026

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

3 out of 5
Midtown Ocean City
Price was $1,769, price is now $1,387 per person
$1,387
per person
Jul 2 - Jul 5
found 20 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
8.4/10 Very Good! (39 reviews)
I loved the dock and the gorgeous sunsets .

Reviewed on Sep 7, 2025

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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
$120 nightly
The price is $133 total per night from Jun 3 to Jun 4
$133 total
Jun 3 - Jun 4
Total with taxes and fees
9.4/10 Exceptional! (1,005 reviews)
"Everything was wonderful about hotel I love my stay"

Reviewed on May 26, 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
$90 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! (1,007 reviews)
"Love the hotel nice n clean plus indoor pool which was a plus due to the weather being rainy and cloudy that's why I picked to stay there. The only thing I would suggest in the pool area is getting some floor fans to keep the floors dry cuz is was slippery being very wet."

Reviewed on May 26, 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 $443 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.