Book Holiday Homes in Greenwood

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Featured Holiday Homes 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
Luxury Treehouse with Large Deck

Luxury Treehouse with Large Deck

Harrington DE
When you stay at this vacation home in Greenwood, you'll be 11 minutes by car from Abbott's Mill Nature Center.
Opens in a new windowLuxury Treehouse with Large Deck
Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!

Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!

Milford DE
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!
Save an average of 15% on thousands of hotels when you're signed in
Beachfront Sunrise - Waterfront house w/ bay and refuge views
Sleeps 6-8 people

Beachfront Sunrise - Waterfront house w/ bay and refuge views Sleeps 6-8 people

Milford DE
When you stay at this vacation home in Milford, you'll be on the beach, just steps from Prime Hook National Wildlife Refuge and Prime Hook Beach.
Opens in a new windowBeachfront Sunrise - Waterfront house w/ bay and refuge views Sleeps 6-8 people
Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

Frederica DE
Located in Frederica, this vacation home is by the sea, within a 15-minute drive of John Dickinson Plantation and Wesley College Dover Air Force Base ...
Opens in a new windowBowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!
Bayfront Cottage with Spectacular Views

Bayfront Cottage with Spectacular Views

Slaughter Beach DE
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
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
Historic home in downtown Milton w/hot tub. Quick drive to the Delaware beaches!

Historic home in downtown Milton w/hot tub. Quick drive to the Delaware beaches!

Milton DE
With a stay at this vacation home in Milton, you'll be within a 5-minute walk of Milton Historical Society and Lydia Black Cannon Museum.
Opens in a new windowHistoric home in downtown Milton w/hot tub. Quick drive to the Delaware beaches!
Pets Friendly,  Waterfront, Large backyard, Bonfire with grill, outside shower

Pets Friendly, Waterfront, Large backyard, Bonfire with grill, outside shower

Milton DE
When you stay at this vacation home in Milton, you'll be on the beach, just steps from Prime Hook Beach and Prime Hook National Wildlife Refuge.
Opens in a new windowPets Friendly, Waterfront, Large backyard, Bonfire with grill, outside shower
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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$116
Highest Price
AU$134
Popular accommodation
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf, Luxury Treehouse with Large Deck, Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!, Beachfront Sunrise - Waterfront house w/ bay and refuge views Sleeps 6-8 people, Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!, Bayfront Cottage with Spectacular Views, Charming 3-bedroom Ranch in delightful Dover with AC, Historic home in downtown Milton w/hot tub. Quick drive to the Delaware beaches!, Pets Friendly, Waterfront, Large backyard, Bonfire with grill, outside shower

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$134 per night from 23 Mar to 24 Mar
AU$134
23 Mar - 24 Mar
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$116 per night from 23 Mar to 24 Mar
AU$116
23 Mar - 24 Mar
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
Save an average of 15% on thousands of hotels when you're signed in
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$124 per night from 22 Mar to 23 Mar
AU$124
22 Mar - 23 Mar
includes taxes & fees
A stay at Microtel Inn & Suites by Wyndham Dover places you in the heart of Dover, within a 5-minute drive of Great Geneva and Blue Hen Mall.
Opens in a new windowMicrotel Inn & Suites by Wyndham Dover
Don't see what you're looking for?
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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.