Greenwood Vacations from $742

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The Latest Greenwood vacation packages

Price found within the past 48 hours. Click for updated prices.
Lankford Hotel and Lodge

Lankford Hotel and Lodge

3.5 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $1,071, price is now $742 per person
$742
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
8.6/10 Excellent! (642 reviews)
The water takes a while to get warm ' no kutchenet was something that was overlooked 'not a place I'd recommend if you're going to be there a while , because you'll be spending more funds eating.

Reviewed on Jun 3, 2026

Ocean 1 Hotel and Suites

Ocean 1 Hotel and Suites

2 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $1,421, price is now $956 per person
$956
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
8.2/10 Very Good! (722 reviews)
The balcony is on top of your neighbors no privacy and railing is all moldy. Fridge didn’t work when we arrived but they did replace it with another. The 2nd shift front desk guy was rude as heck. He parked in the lane that you had to drive in and back out of and there was plenty of parking. If an occupant had done that they would have been towed. He never said “hi” when you walked by. The day girl was great. The wallpaper was coming off the walls in our room. I would choose another place next time

Reviewed on Jun 4, 2026

Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $1,846, price is now $1,258 per person
$1,258
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) 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

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was $2,830, price is now $2,010 per person
$2,010
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)
This is our go-to spot for enjoying a beach getaway. It’s centrally located between Rehoboth Beach and Ocean City. The pool is nice and everything is clean. We appreciate the quiet pace of the hotel.

Reviewed on Jun 4, 2026

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $1,801, price is now $1,312 per person
$1,312
per person
Aug 18 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Salisbury (SBY)
9/10 Wonderful! (3,600 reviews)
Didn’t like the balcony. Didn’t have any privacy. The rooms are separated by wrought iron fencing. Everything else was nice

Reviewed on Jun 6, 2026

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Greenwood Hotel Deals

Luxury Treehouse with Large Deck

Luxury Treehouse with Large Deck

Harrington DE
10/10 Exceptional! (28 reviews)
"Absolutely amazing!! Everyone needs to go!!!"

Reviewed on Jun 2, 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
$132 nightly
The price is $147 total per night from Jun 10 to Jun 11
$147 total
Jun 10 - Jun 11
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
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $75 total per night from Jun 14 to Jun 15
$75 total
Jun 14 - Jun 15
Total with taxes and fees
8.2/10 Very Good! (1,005 reviews)
"The room was very clean and comfortable. Couldn’t get the icemaker to work properly."

Reviewed on Jun 3, 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 $742 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.