Greenwood Vacations from $268

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The Latest Greenwood vacation packages

Price found within the past 48 hours. Click for updated prices.
The Americana Hotel

The Americana Hotel

2.5 out of 5
Downtown Ocean City
Price was $330, price is now $268 per person
$268
per person
Dec 26 - Dec 29
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
8.6/10 Excellent! (1,080 reviews)
i have no complaints except that i was shocked that they charged $10 to park in the parking lot! I've stayed in other beach front hotels on the boardwalk and never been charged a fee for parking. Why isn't that included in the cost of the room?

Reviewed on Oct 23, 2025

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $383, price is now $309 per person
$309
per person
Dec 26 - Dec 29
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
9/10 Wonderful! (3,258 reviews)
They view was absolutely breath taking. The staff was extremely helpful and friendly.

Reviewed on Oct 21, 2025

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $567, price is now $458 per person
$458
per person
Dec 26 - Dec 29
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
8.8/10 Excellent! (1,008 reviews)
Very professionally cleaned. Safe.

Reviewed on Oct 15, 2025

Cypress River Inn & Spa

Cypress River Inn & Spa

5 out of 5
Price was $685, price is now $564 per person
$564
per person
Dec 26 - Dec 29
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
No reviews
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 $831, price is now $711 per person
$711
per person
Dec 26 - Dec 29
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
9/10 Wonderful! (763 reviews)
Bugs on window sill in dining area. Grease trap on sidewalk was leaking. All other public areas were EXCELLENT. Housekeeping could have cleaned the toilet . Greeter in load/unload area was very helpful and pleasant. I think his name was Olem. Front desk staff was pleasant and friendly and knowledgeable. Overall we have no complaints. We had a pleasant stay.

Reviewed on Oct 1, 2025

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Greenwood Hotel Deals

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 $98 total per night from Nov 3 to Nov 4
$98 total
Nov 3 - Nov 4
Total with taxes and fees
9.4/10 Exceptional! (1,014 reviews)
Parking was safe and easy. Hotel was very clean. Gym and pool area was very clean. Staff was exceptional from check in to housekeeping. Would definitely stay again.

Reviewed on Oct 19, 2025

Home2 Suites by Hilton Lewes Rehoboth Beach
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
$106 nightly
The price is $118 total per night from Oct 30 to Oct 31
$118 total
Oct 30 - Oct 31
Total with taxes and fees
9.2/10 Wonderful! (971 reviews)
The room was amazing and clean. Traveling on a girl's trip and felt very safe and secure while in your city. Wonderful experience.

Reviewed on Oct 15, 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
$98 nightly
The price is $108 total per night from Nov 9 to Nov 10
$108 total
Nov 9 - Nov 10
Total with taxes and fees
8.8/10 Excellent! (480 reviews)
Very nice facility. Room was clean. Loved the atmosphere of the place. Good breakfast.

Reviewed on Oct 17, 2025

Tru by Hilton Georgetown
See all 649 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 $268 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.