Greenwood Vacations from $505

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The Latest Greenwood vacation packages

Price found within the past 48 hours. Click for updated prices.
The Inn at Lewes

The Inn at Lewes

3 out of 5
Price was $629, price is now $505 per person
$505
per person
Jul 6 - Jul 10
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
6.2/10 (97 reviews)
This was the best place I stayed. However, it was not at the Inn for which I paid. When I arrived, no one was in the office, but I ran into some guys renovating the property. The called the boss for me, and he put me at a much nicer property at Staybridge Suites, 34521 Old Postal Lane, Lewes. That was the nicest place Instayed on this vacations so far and the breakfast was the best. The WiFi was flawless.

Reviewed on May 17, 2026

The Surf Shanty Motel

The Surf Shanty Motel

2.5 out of 5
Save 100% on your flight
Price was $902, price is now $680 per person
$680
per person
Jul 6 - Jul 10
found 14 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
9.8/10 Exceptional! (319 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
Price was $1,640, price is now $1,300 per person
$1,300
per person
Aug 2 - Aug 6
found 7 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Salisbury (SBY)
9.6/10 Exceptional! (759 reviews)
Love this hotel! Has everything I need, great location and love the space!

Reviewed on May 27, 2026

Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Downtown Bethany Beach
Price was $2,199, price is now $1,821 per person
$1,821
per person
Aug 2 - Aug 6
found 7 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Salisbury (SBY)
9/10 Wonderful! (826 reviews)
Great location, very close to everything in town & beach. The rooms & property were very clean & well maintained.

Reviewed on May 27, 2026

The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
Price was $1,269, price is now $1,077 per person
$1,077
per person
Aug 17 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
8.6/10 Excellent! (1,202 reviews)
This was the perfect little getaway in a great location.

Reviewed on May 27, 2026

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Greenwood Hotel Deals

Luxury Treehouse with Large Deck

Luxury Treehouse with Large Deck

Harrington DE
10/10 Exceptional! (27 reviews)
"It was a great location and great place for what we hoped to achieve. Rest, relaxation, and quiet time. The listing was represented perfectly, and the hostess was very easy to connect with. Her pup, Eddie, was adorable when he visited during our stay! :) Would definitely stay here again."

Reviewed on May 28, 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
$135 nightly
The price is $150 total per night from Jun 7 to Jun 8
$150 total
Jun 7 - Jun 8
Total with taxes and fees
9.4/10 Exceptional! (1,000 reviews)
"Everything was wonderful about hotel I love my stay"

Reviewed on May 26, 2026

Hyatt House Lewes/Rehoboth Beach
Microtel Inn & Suites by Wyndham Dover

Microtel Inn & Suites by Wyndham Dover

2 out of 5
1703 E Lebanon Rd Dover DE
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $75 total per night from Jun 29 to Jun 30
$75 total
Jun 29 - Jun 30
Total with taxes and fees
8.2/10 Very Good! (1,002 reviews)
"A suggestion: There was no bar for safe in and out access in the shower. Even a mat would be helpful."

Reviewed on May 30, 2026

Microtel Inn & Suites by Wyndham Dover
See all 625 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 $505 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.