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 10-minute drive of Dover International Speedway and Carrolls Center Shopping Center.
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 23.3 mi (37.4 km) from Dover International Speedway and 7.8 mi (12.5 km) from DE Turf ...
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$112
Highest Price
AU$128
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

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$115 per night from 15 Feb to 16 Feb
AU$115
15 Feb - 16 Feb
includes taxes & fees
Located in Lewes, Home2 Suites by Hilton Lewes Rehoboth Beach is within a 15-minute drive of Rehoboth Beach Boardwalk and Lewes Beach.
Opens in a new windowHome2 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
The price is AU$128 per night from 5 Feb to 6 Feb
AU$128
5 Feb - 6 Feb
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
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$112 per night from 1 Mar to 2 Mar
AU$112
1 Mar - 2 Mar
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 International Speedway and Great ...
Opens in a new windowMicrotel Inn & Suites by Wyndham Dover
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Quality Inn & Suites Harrington - Milford

Quality Inn & Suites Harrington - Milford

2.5 out of 5
1259 Corn Crib Road Harrington DE
Fully refundableReserve now, pay when you stay
The price is AU$114 per night from 22 Feb to 23 Feb
AU$114
22 Feb - 23 Feb
includes taxes & fees
Located in Harrington, Quality Inn & Suites Harrington - Milford is within a 15-minute walk of Harrington Raceway and Casino and Delaware State Fairgrounds.
Opens in a new windowQuality Inn & Suites Harrington - Milford
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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.