Book Holiday Homes in Greenwood

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Featured Holiday Homes in Greenwood

Charming 3-bedroom Ranch in delightful Dover with AC

Charming 3-bedroom Ranch in delightful Dover with AC

Dover DE
With a stay at this vacation home in Dover, you'll be within a 5-minute drive of Carrolls Center Shopping Center and Great Geneva.
Opens in a new windowCharming 3-bedroom Ranch in delightful Dover with AC
Cozy cottage on the Miller farm.

Cozy cottage on the Miller farm.

Milford DE
Located in Milford, this vacation home is a 1-minute drive from Abbott's Mill Nature Center and 7 minutes from Second Street Players - Riverfront Theatre.
Opens in a new windowCozy cottage on the Miller farm.
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
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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Family friendly home w/  360 views of the bay and wild life preserve (sleeps 12)

Family friendly home w/ 360 views of the bay and wild life preserve (sleeps 12)

Milton DE
Located in Milton, this vacation home is on the waterfront, within a 5-minute walk of Prime Hook National Wildlife Refuge and Beach Plum Island Nature ...
Opens in a new windowFamily friendly home w/ 360 views of the bay and wild life preserve (sleeps 12)
Wind Song Getaway on the Beach

Wind Song Getaway on the Beach

Frederica DE
When you stay at this vacation home in Frederica, you'll be on the beach and 15 minutes by car from John Dickinson Plantation.
Opens in a new windowWind Song Getaway on the Beach
Spacious Coastal Home perfect for Holidays! Large game room. 5 minutes to beach!

Spacious Coastal Home perfect for Holidays! Large game room. 5 minutes to beach!

2 out of 5
Lewes DE
Located in Lewes, this vacation home is within a 15-minute drive of Rehoboth Beach Boardwalk and Lewes Beach.
Opens in a new windowSpacious Coastal Home perfect for Holidays! Large game room. 5 minutes to beach!
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 DE
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
Secluded Beach home with amazing views.

Secluded Beach home with amazing views.

Milford DE
With a stay at this vacation home in Milford, you'll be on the beach, and 7.8 mi (12.5 km) from DE Turf Sports Complex and 12.8 mi (20.7 km) from Killens Pond ...
Opens in a new windowSecluded Beach home with amazing views.
Piper's Paradise -  Beachfront, Views, Sonos, Sauna, Tesla charger, Arcade

Piper's Paradise - Beachfront, Views, Sonos, Sauna, Tesla charger, Arcade

Milton DE
With a stay at this vacation home in Milton, you'll be on the beach, just a 1-minute walk from Prime Hook National Wildlife Refuge and 7 minutes by foot from ...
Opens in a new windowPiper's Paradise - Beachfront, Views, Sonos, Sauna, Tesla charger, Arcade
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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
363 Holiday Homes
Lowest Price
AU$124
Highest Price
AU$179
Popular accommodation
Charming 3-bedroom Ranch in delightful Dover with AC, Cozy cottage on the Miller farm. , Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf, Family friendly home w/ 360 views of the bay and wild life preserve (sleeps 12), Wind Song Getaway on the Beach, Spacious Coastal Home perfect for Holidays! Large game room. 5 minutes to beach!, Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf, Secluded Beach home with amazing views. , Piper's Paradise - Beachfront, Views, Sonos, Sauna, Tesla charger, Arcade

Top trending hotels in Greenwood

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
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
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$140 per night from 6 Jan to 7 Jan
AU$140
6 Jan - 7 Jan 2026
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$124 per night from 24 Dec to 25 Dec
AU$124
24 Dec - 25 Dec
includes taxes & fees
Located in Lewes, Home2 Suites by Hilton Lewes Rehoboth Beach is within a 15-minute drive of Tanger Outlets and Rehoboth Beach Boardwalk.
Opens in a new windowHome2 Suites by Hilton Lewes Rehoboth Beach
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Home2 Suites by Hilton Dover, DE

Home2 Suites by Hilton Dover, DE

3 out of 5
222 S Dupont Hwy Dover DE
Fully refundableReserve now, pay when you stay
The price is AU$179 per night from 21 Dec to 22 Dec
AU$179
21 Dec - 22 Dec
includes taxes & fees
With a stay at Home2 Suites by Hilton Dover, DE, you'll be centrally located in Dover, just a 4-minute walk from Edgehill Shopping Center and 8 minutes by foot ...
Opens in a new windowHome2 Suites by Hilton Dover, DE
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See all available properties in Greenwood
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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.