Greenwood Vacations from $529

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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 $673, price is now $529 per person
$529
per person
Jul 31 - Aug 3
found 20 hours ago
Roundtrip flight included
Cleveland (CLE) 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

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was $2,859, price is now $2,042 per person
$2,042
per person
Aug 30 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) to Salisbury (SBY)
9.6/10 Exceptional! (764 reviews)
Paying 16 dollars to park in the parking lot

Reviewed on Jun 7, 2026

Americana Condos 10th street

Americana Condos 10th street

3.5 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $2,194, price is now $1,645 per person
$1,645
per person
Aug 18 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
8.4/10 Very Good! (19 reviews)
No complaints it was super nice! Will definitely book again

Reviewed on May 26, 2026

Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Price was $1,160, price is now $887 per person
$887
per person
Aug 18 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
7.6/10 Good! (95 reviews)
Everything was exactly what you would expect for a budget friendly room, only complaint was that the steps and porch going to 3rd floor was sketchy and theres a large soft spot on 3rd floor side landing

Reviewed on Oct 17, 2025

Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $1,819, price is now $1,400 per person
$1,400
per person
Aug 30 - Sep 4
found 1 day ago
Roundtrip non-stop flight included
New York (LGA) 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! (29 reviews)
"My son had a lacrosse tourney at DE Turf complex, this property is only 25 min which was perfect. It was so nice to have a very clean & comfortable place to stay nearby with a full fridge, washer/dryer, kitchen & the cutest porch to relax after a long day. Beds are extremely comfortable, linens soft, ..."

Reviewed on Jun 8, 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
$143 nightly
The price is $159 total per night from Jun 14 to Jun 15
$159 total
Jun 14 - Jun 15
Total with taxes and fees
9.4/10 Exceptional! (1,009 reviews)
"The staff is so personable. Jamie, the night manager, knows us by name and welcomes us as soon as she saw us. The hotel is always clean with a great staff."

Reviewed on Jun 7, 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
$72 nightly
The price is $78 total per night from Jun 28 to Jun 29
$78 total
Jun 28 - Jun 29
Total with taxes and fees
8.2/10 Very Good! (1,010 reviews)
"Great"

Reviewed on Jun 8, 2026

Microtel Inn & Suites by Wyndham Dover
See all 660 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 $529 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.