Greenwood Vacations from $779

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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 $1,199, price is now $779 per person
$779
per person
Aug 3 - Aug 8
found 1 day 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

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Save 100% on your flight
Price was $1,876, price is now $1,186 per person
$1,186
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
9.4/10 Exceptional! (753 reviews)
Location, it’s proximity to Ocean City as well as Bethany Beach and Dewey Beach! Within walking distance of some of our favorite restaurants.

Reviewed on May 19, 2026

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

3 out of 5
Midtown Ocean City
Save 100% on your flight
Price was $1,882, price is now $1,252 per person
$1,252
per person
Jul 3 - Jul 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
8.4/10 Very Good! (39 reviews)
I loved the dock and the gorgeous sunsets .

Reviewed on Sep 7, 2025

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $1,470, price is now $986 per person
$986
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
9/10 Wonderful! (3,574 reviews)
My only complaint was the outside pool was empty. Other then that the hotel was excellent.

Reviewed on May 19, 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 1 day ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
8.8/10 Excellent! (1,000 reviews)
I have stayed at this property for the past number of years. And in all that time I've had only one inconvenience. The fridge did not work. However, the staff did everything possible to fix or replace the fridge. Neither could be done, so when I checked out the manager most

Reviewed on May 18, 2026

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Greenwood Hotel Deals

Luxury Treehouse with Large Deck

Luxury Treehouse with Large Deck

Harrington DE
10/10 Exceptional! (25 reviews)
"This was the perfect spot for our honeymoon and was so beautiful and relaxing! Everything was very clean and just done perfectly. We thoroughly enjoyed taking walks daily and befriending the cows, Eddie, and the farm cats and it was overall an amazing trip. If we come back in the area, we will definitely ..."

Reviewed on May 18, 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
$118 nightly
The price is $131 total per night from Jun 3 to Jun 4
$131 total
Jun 3 - Jun 4
Total with taxes and fees
9.4/10 Exceptional! (1,004 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
$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! (1,008 reviews)
"Very nice place to stay. Would definitely go back"

Reviewed on May 19, 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 $779 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.