Greenwood Vacations from $743

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The Latest Greenwood vacation packages

Price found within the past 48 hours. Click for updated prices.
Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD

2 out of 5
Price was $854, price is now $743 per person
$743
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Salisbury (SBY)
15.2/10 Exceptional! (56 reviews)
Staff was courteous, but slow in directing to a room that needed a short approach due to mobility issues. ,(500 ft exterior walk is not user friendly &mobility challenge. Third time into office for room placement. Lock card did not work,after 1 night, No toiletries, a bar of soap! No cable print guide. Room amenities very poor. Ads said it had been renovated,but rooms sure did not look it. Overall poor communication,but one observant worker noticed people were moving about and opened the free breakfast 30 min early. Competitor- Red Roof Inn was all that this wasn't.

Reviewed on Nov 9, 2025

Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $2,156, price is now $1,558 per person
$1,558
per person
Jan 1 - Jan 4
found 8 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Salisbury (SBY)
15.2/10 Exceptional! (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

Howard Johnson Plaza Hotel by Wyndham Ocean City Oceanfront

Howard Johnson Plaza Hotel by Wyndham Ocean City Oceanfront

2.5 out of 5
Downtown Ocean City
Price was $1,416, price is now $1,185 per person
$1,185
per person
Jan 1 - Jan 4
found 8 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Salisbury (SBY)
18.4/10 Exceptional! (1,112 reviews)
Not much to do during off season here. Since, it's a Howard Johnson's you would expect a Howard Johnson restaurant to be there right? Nope. I'm sure during the summer the place is hoping. Other good places around to eat thankfully. Not bad place.

Reviewed on Nov 22, 2025

Comfort Inn Ocean City Boardwalk

Comfort Inn Ocean City Boardwalk

2.5 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $5,694, price is now $4,836 per person
$4,836
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Salisbury (SBY)
18/10 Exceptional! (1,003 reviews)
Very friendly staff! Efficient check-in process and a nice clean room with a mini kitchen.

Reviewed on Nov 22, 2025

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

3 out of 5
Midtown Ocean City
Price was $856, price is now $750 per person
$750
per person
Jan 1 - Jan 4
found 8 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Salisbury (SBY)
16.8/10 Exceptional! (39 reviews)
I loved the dock and the gorgeous sunsets .

Reviewed on Sep 7, 2025

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Greenwood Hotel Deals

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
$82 nightly
The price is $91 total per night from Dec 1 to Dec 2
$91 total
Dec 1 - Dec 2
Total with taxes and fees
9.2/10 Wonderful! (994 reviews)
Staff was very friendly. Room's studio design was different but functional and we enjoyed it. Overall the room, kitchen and bathroom areas were very clean.

Reviewed on Nov 21, 2025

Hyatt House Lewes/Rehoboth Beach
Tru by Hilton Georgetown

Tru by Hilton Georgetown

2.5 out of 5
301 College Park Lane Georgetown DE
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $100 total per night from Dec 14 to Dec 15
$100 total
Dec 14 - Dec 15
Total with taxes and fees
8.8/10 Excellent! (495 reviews)
We had a great time, looking forward to the next visit.

Reviewed on Nov 14, 2025

Tru by Hilton Georgetown
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
$67 nightly
The price is $75 total per night from Nov 30 to Dec 1
$75 total
Nov 30 - Dec 1
Total with taxes and fees
9.4/10 Exceptional! (1,005 reviews)
Our stay there was wonderful nice hotel clean and comfy and very nice staff. Definitely will be returning.

Reviewed on Nov 19, 2025

Home2 Suites by Hilton Lewes Rehoboth Beach
See all 644 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 $743 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.