Greenwood Vacations from $496

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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 $610, price is now $496 per person
$496
per person
Mar 20 - Mar 27
found 2 hours ago
Roundtrip flight included
Minneapolis (MSP) to Salisbury (SBY)
7.2/10 Good! (415 reviews)
Clean and friendly staff. Good location.

Reviewed on Jan 2, 2026

Harrington Welcome Inn

Harrington Welcome Inn

2.5 out of 5
Save 100% on your flight
Price was $1,159, price is now $730 per person
$730
per person
Mar 20 - Mar 27
found 2 hours ago
Roundtrip flight included
Minneapolis (MSP) to Salisbury (SBY)
7.4/10 Good! (146 reviews)
Very cheap we usually book there late minute Just to get away.. quiet and convenient.. I clean every time we go. But today was too much. The shower curtain was dirty and moldy. Bathtub dirty and water filled up when taking a shower. Clogged drain. . I don't complain because it's a cheap motel. But they definitely need to hire a new house keeper . Nobody checks behind them? Omg!

Reviewed on Dec 25, 2025

Comfort Inn & Suites Milford

Comfort Inn & Suites Milford

2.5 out of 5
Price was $859, price is now $700 per person
$700
per person
Mar 20 - Mar 27
found 2 hours ago
Roundtrip flight included
Minneapolis (MSP) to Salisbury (SBY)
8/10 Very Good! (614 reviews)
Very clean! No noise! Great staff!

Reviewed on Nov 30, 2025

Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHG

Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHG

2.5 out of 5
Price was $788, price is now $686 per person
$686
per person
Mar 20 - Mar 27
found 3 hours ago
Roundtrip flight included
Minneapolis (MSP) to Salisbury (SBY)
9/10 Wonderful! (1,001 reviews)
I stayed with this hotel chain because it is one of my favorite chains. This is the first time in 10 years that I was disappointed. The staff wasn't as friendly as I am normally use to. The shower wasn't cleaned properly. When the water began to run old soap scum ran into the shower and on my feet. This isn't the normal standards that I am use to experiencing with this chain and won't utilize this property again.

Reviewed on Oct 16, 2025

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
Price was $726, price is now $645 per person
$645
per person
Mar 20 - Mar 27
found 2 hours ago
Roundtrip flight included
Minneapolis (MSP) to Salisbury (SBY)
8.6/10 Excellent! (847 reviews)
The controls on motorized blinds did not work. No milk for cereal 2 out of 3 days. Very slow to stock breakfast items. There was second TV but remote missing and wifi was si slow we couldn't actually use it. Beds were comfortable and room matched description.

Reviewed on Dec 21, 2025

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Greenwood Hotel Deals

Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

Greenwood DE
9.8/10 Exceptional! (32 reviews)
Great property for a family stay.Close to our event in Milford DE

Reviewed on Dec 4, 2025

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Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf
Luxury Treehouse with Large Deck

Luxury Treehouse with Large Deck

Harrington DE
10/10 Exceptional! (14 reviews)
The stay was absolutely amazing. It was truly peaceful, the view was beautiful, the feeling of a nice cozy family home.

Reviewed on Dec 28, 2025

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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
$89 nightly
The price is $99 total per night from Jan 12 to Jan 13
$99 total
Jan 12 - Jan 13
Total with taxes and fees
9.2/10 Wonderful! (1,009 reviews)
Everything was exceptional! Will definitely recommend

Reviewed on Jan 1, 2026

Hyatt House 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 $496 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.