Greenwood Vacations from $430

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The Latest Greenwood vacation packages

Price found within the past 48 hours. Click for updated prices.
Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Price was $556, price is now $430 per person
$430
per person
Sep 3 - Sep 6
found 12 hours ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
8.8/10 Excellent! (1,000 reviews)
It is always a great experience and the staff is very helpful and welcoming.

Reviewed on Jun 27, 2026

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Save 100% on your flight
Price was $926, price is now $651 per person
$651
per person
Sep 3 - Sep 6
found 12 hours ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
9.4/10 Exceptional! (774 reviews)
We had such a fantastic time! Incredible, attentive staff, steps away from the beach and the amenities were well kept.

Reviewed on Jun 22, 2026

Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Downtown Bethany Beach
Save 100% on your flight
Price was $1,307, price is now $1,010 per person
$1,010
per person
Sep 3 - Sep 6
found 12 hours ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
9/10 Wonderful! (842 reviews)
Great location. Spacious rooms. Great AC. Poorly maintained facility. Staff is poorly trained. Not what I would expect for the price paid.

Reviewed on Jun 11, 2026

Boardwalk One

Boardwalk One

3 out of 5
Downtown Ocean City
Price was $1,157, price is now $945 per person
$945
per person
Aug 18 - Aug 21
found 19 hours ago
Roundtrip flight included
Philadelphia (PHL) 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

Hyatt House Lewes/Rehoboth Beach

Hyatt House Lewes/Rehoboth Beach

3.5 out of 5
Price was $789, price is now $649 per person
$649
per person
Sep 3 - Sep 6
found 12 hours ago
Roundtrip flight included
New York (NYC) to Salisbury (SBY)
9.4/10 Exceptional! (1,013 reviews)
Everything was great! Staff very accommodating and nice. Nice big pool, great for kids! Breakfast and bar food were great! Located in a quiet spot and close enough to everything!

Reviewed on Jun 25, 2026

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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
$169 nightly
The price is $188 total per night from Jun 28 to Jun 29
$188 total
Jun 28 - Jun 29
Total with taxes and fees
9.4/10 Exceptional! (1,001 reviews)
"I had a pleasant stay and would happily return"

Reviewed on Jun 26, 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 Jul 28 to Jul 29
$75 total
Jul 28 - Jul 29
Total with taxes and fees
8.2/10 Very Good! (1,007 reviews)
"Great room! Very clean and comfortable"

Reviewed on Jun 26, 2026

Microtel Inn & Suites by Wyndham Dover
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
$157 nightly
The price is $175 total per night from Jul 5 to Jul 6
$175 total
Jul 5 - Jul 6
Total with taxes and fees
9.4/10 Exceptional! (1,000 reviews)
"The amenities were awesome and staff was helpful and friendly."

Reviewed on Jun 23, 2026

Home2 Suites by Hilton Lewes Rehoboth Beach
See all 698 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 $430 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.