Book Holiday Homes in Greenwood

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Featured Holiday Homes in Greenwood

Bayfront Cottage with Spectacular Views

Bayfront Cottage with Spectacular Views

Slaughter Beach
With a stay at this vacation home in Milford, you'll be on the beach, just steps from Slaughter Beach and a 2-minute drive from Prime Hook National Wildlife ...
Opens in a new windowBayfront Cottage with Spectacular Views
Cozy Waterfront Cottage– Dog Friendly & Fully Stocked!

Cozy Waterfront Cottage– Dog Friendly & Fully Stocked!

Milford
When you a stay at this vacation home in Milford, you'll be on the waterfront, just steps from Prime Hook National Wildlife Refuge and Prime Hook Beach.
Opens in a new windowCozy Waterfront Cottage– Dog Friendly & Fully Stocked!
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
Located in Greenwood, this vacation home is in a rural location, within a 15-minute drive of T.S. Smith & Sons and Bridgeville Historical Society Museum.
Opens in a new windowBackroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf
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Captain's Quarters

Captain's Quarters

Frederica
When you stay at this vacation home in Frederica, you'll be near the beach and 14 minutes by car from John Dickinson Plantation.
Opens in a new windowCaptain's Quarters
Great Escape ~Unique Beach Views ~ Right on the Water~Child Items ~ Linens

Great Escape ~Unique Beach Views ~ Right on the Water~Child Items ~ Linens

Milton
Located in Milton, this vacation home is on the beach, within a 5-minute walk of Prime Hook National Wildlife Refuge and Beach Plum Island Nature Preserve.
Opens in a new windowGreat Escape ~Unique Beach Views ~ Right on the Water~Child Items ~ Linens
Historic home, great yard & Walk to Dogfish Head Brewery!

Historic home, great yard & Walk to Dogfish Head Brewery!

Milton, DE
With a stay at this vacation home in Milton, you'll be within a 10-minute walk of Dogfish Head Craft Brewery and Milton Theater.
Opens in a new windowHistoric home, great yard & Walk to Dogfish Head Brewery!
Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!

Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!

2 out of 5
Milford
With a stay at this vacation home in Milford, you'll be on the beach, just steps from Slaughter Beach and a 2-minute drive from Prime Hook National Wildlife ...
Opens in a new windowWelcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!
Lee's Place Brand New 2BR Townhouse w/free parking

Lee's Place Brand New 2BR Townhouse w/free parking

Milford
Located in Milford, this vacation home is within a 5-minute drive of Second Street Players - Riverfront Theatre and Live Cheap & Make Art Studios.
Opens in a new windowLee's Place Brand New 2BR Townhouse w/free parking
Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

Frederica
When you stay at this vacation home in Frederica, you'll be near the beach and 15 minutes by car from John Dickinson Plantation.
Opens in a new windowCharming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf
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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.

Greenwood Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Greenwood vacation homes are the perfect way for you to wing it.

Holiday houses in Greenwood let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Greenwood in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Greenwood adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Greenwood with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Greenwood vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Greenwood Holiday Homes essential information

Accommodation
356 Holiday Homes
Lowest Price
AU$141
Highest Price
AU$190
Popular accommodation
Bayfront Cottage with Spectacular Views, Cozy Waterfront Cottage– Dog Friendly & Fully Stocked!, Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf, Captain's Quarters, Great Escape ~Unique Beach Views ~ Right on the Water~Child Items ~ Linens, Historic home, great yard & Walk to Dogfish Head Brewery!, Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!, Lee's Place Brand New 2BR Townhouse w/free parking, Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

Top trending hotels in Greenwood

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
The price is AU$180 per night from 28 Oct to 29 Oct
AU$180
28 Oct - 29 Oct
includes taxes & fees
Located in Lewes, Hyatt House Lewes/Rehoboth Beach is within a 10-minute drive of Cape Henlopen State Park and Cape May - Lewes Ferry.
Opens in a new windowHyatt House Lewes/Rehoboth Beach
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
The price is AU$151 per night from 27 Oct to 28 Oct
AU$151
27 Oct - 28 Oct
includes taxes & fees
With a stay at Home2 Suites by Hilton Lewes Rehoboth Beach in Lewes, you'll be within a 10-minute drive of Cape Henlopen State Park and Cape May - Lewes ...
Opens in a new windowHome2 Suites by Hilton 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
The price is AU$190 per night from 6 Oct to 7 Oct
AU$190
6 Oct - 7 Oct
includes taxes & fees
With a stay at Tru by Hilton Georgetown in Georgetown, you'll be within a 5-minute drive of Delaware Technical Community College Georgetown Campus and Georgetown ...
Opens in a new windowTru by Hilton Georgetown
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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
The price is AU$141 per night from 9 Oct to 10 Oct
AU$141
9 Oct - 10 Oct
includes taxes & fees
With a stay at Microtel Inn & Suites by Wyndham Dover, you'll be centrally located in Dover, within a 10-minute drive of Dover Downs Casino and Dover International ...
Opens in a new windowMicrotel Inn & Suites by Wyndham Dover
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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.

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^Subject to availability and chosen travel dates.