Greenwood Vacations from $308

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The Latest Greenwood vacation packages

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
Price was $352, price is now $308 per person
$308
per person
Feb 28 - Mar 4
found 18 hours ago
Roundtrip non-stop flight included
St. Louis (STL) to Salisbury (SBY)
7.2/10 Good! (415 reviews)
Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish.

Reviewed on Jan 16, 2026

Harrington Welcome Inn

Harrington Welcome Inn

2.5 out of 5
Save 100% on your flight
Price was $591, price is now $422 per person
$422
per person
Feb 28 - Mar 4
found 18 hours ago
Roundtrip non-stop flight included
St. Louis (STL) to Georgetown (GED)
7.4/10 Good! (146 reviews)
The hotel manager lady was amazing and treated me with amazing respect. Plus she always makes me smile.

Reviewed on Jan 21, 2026

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $928, price is now $794 per person
$794
per person
Apr 1 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
9/10 Wonderful! (3,316 reviews)
The hotel is great has everything you need to stay w your family a pool, restaurant, games for kids. The mattress was a little hard my only complaint but other wise great place to stay w kids.

Reviewed on Jan 24, 2026

Ashore Resort & Beach Club

Ashore Resort & Beach Club

3.5 out of 5
North Ocean City
Price was $861, price is now $740 per person
$740
per person
Apr 1 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
8.2/10 Very Good! (1,825 reviews)
Clean, comfortable and quiet.

Reviewed on Dec 28, 2025

Country Inn & Suites by Radisson, Salisbury, MD

Country Inn & Suites by Radisson, Salisbury, MD

3 out of 5
Price was $941, price is now $843 per person
$843
per person
Apr 1 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Salisbury (SBY)
7.4/10 Good! (1,002 reviews)
Affordable and clean

Reviewed on Jan 22, 2026

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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
$73 nightly
The price is $81 total per night from Feb 15 to Feb 16
$81 total
Feb 15 - Feb 16
Total with taxes and fees
9.4/10 Exceptional! (1,014 reviews)
Couldn't believe they plant based chicken strips on the buffet. Would be great to also have 21 grain bread and a plant based butter or cream cheese, but the plant based chicken strips is a great start. Also, the front desk team was awesome.

Reviewed on Jan 23, 2026

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
$81 nightly
The price is $90 total per night from Feb 1 to Feb 2
$90 total
Feb 1 - Feb 2
Total with taxes and fees
9.2/10 Wonderful! (1,012 reviews)
Very clean. Great menu and taste.

Reviewed on Jan 19, 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
$73 nightly
The price is $79 total per night from Feb 1 to Feb 2
$79 total
Feb 1 - Feb 2
Total with taxes and fees
8/10 Very Good! (1,002 reviews)
Excellent property, well maintained, clean and courteous staff. Seems like new construction. Water in the lobby retail shop is only $1. Couldn't ask for more.

Reviewed on Jan 18, 2026

Microtel Inn & Suites by Wyndham Dover
See all 640 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 $308 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.