Greenwood Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Greenwood vacation rentals

Smart TV, computer monitors
1st Floor Beach-town Condo. We are Pet Friendly!

Condo in Villages of Five Points

1st Floor Beach-town Condo. We are Pet Friendly!
10.0 out of 10, Exceptional, (32)
"We thoroughly enjoyed our stay at our condo! It was very clean and we felt right at home. The 2 pools were an added bonus and the location was close to the beach, shops, and restaurants. We hope to return in the future!"
United States
Lauren S.
The price is ￥13,714
￥44,185 total
includes taxes & fees
Dec 23 - Dec 24
1st Floor Beach-town Condo. We are Pet Friendly!
Interior
Elegant 3-Bedroom Condo in Lewes with Pond Views

Condo in Plantations East

Elegant 3-Bedroom Condo in Lewes with Pond Views
9.8 out of 10, Exceptional, (20)
"Amazing location!!!!"
United States
Tania W.
The price is ￥10,884
￥39,207 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Elegant 3-Bedroom Condo in Lewes with Pond Views
Beach
Specious & Cozy. Close to Lewes and Rehoboth Beaches. Community Pool

Apartment in Lewes

Specious & Cozy. Close to Lewes and Rehoboth Beaches. Community Pool
10.0 out of 10, Exceptional, (2)
"Great condo. Fantastic pool. Close to nice Family Beach."
United States
Mary K.
The price is ￥15,574
￥41,816 total
includes taxes & fees
Dec 14 - Dec 15
Specious & Cozy. Close to Lewes and Rehoboth Beaches. Community Pool
Exterior detail
Historic home, great yard & Walk to Dogfish Head Brewery!

Vacation Home in Milton

Historic home, great yard & Walk to Dogfish Head Brewery!
9.8 out of 10, Exceptional, (7)
"We had a great experience! It was clean, cozy, and had easy access to a number of locations. Will book again!"
United States
Jeffrey
The price is ￥12,906
￥22,039 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Historic home, great yard & Walk to Dogfish Head Brewery!
Pool
The Little house W/ Pool & Spa

Mobile Home in Lincoln

The Little house W/ Pool & Spa
10.0 out of 10, Exceptional, (1)
"Marissa was very attentive in answering my questions quickly! The house was perfect for myself and my small dog! It was in close proximity to all the beaches. The bed was super comfortable. The house was spotless. All of the decor in the house was absolutely adorable! Perfect weekend getaway! Thank you for sharing your tiny home! "
United States
Katherine P.
The price is ￥15,730
￥37,702 total
includes taxes & fees
Jan 12 - Jan 13, 2026
The Little house W/ Pool & Spa
Exterior
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

Vacation Home in Georgetown

EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
9.8 out of 10, Exceptional, (47)
"Very thoughtful and hospitable hosts. We had a lovely time!"
United States
Eve S.
The price is ￥13,994
￥30,484 total
includes taxes & fees
Dec 15 - Dec 16
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
Beach nearby
Spacious Home-Steps Away From Quiet Beach-Nature and Wildlife-Pet Friendly!

Vacation Home in Milford

Spacious Home-Steps Away From Quiet Beach-Nature and Wildlife-Pet Friendly!
9.6 out of 10, Exceptional, (17)
"An amazing beach area that shows the oceans natural beauty! Neighborhood is extremely quiet and welcoming. "
United States
Frank R.
The price is ￥20,851
￥56,929 total
includes taxes & fees
Dec 16 - Dec 17
Spacious Home-Steps Away From Quiet Beach-Nature and Wildlife-Pet Friendly!
On the beach
Pets Friendly, Waterfront, Large backyard, Bonfire with grill, outside shower

Vacation Home in Milton

Pets Friendly, Waterfront, Large backyard, Bonfire with grill, outside shower
10.0 out of 10, Exceptional, (12)
"The host was very friendly and responsive. We love taking our puppy to her first trip to the beach!"
United States
Mary-Liz E.
The price is ￥23,361
￥53,224 total
includes taxes & fees
Dec 13 - Dec 14
Pets Friendly, Waterfront, Large backyard, Bonfire with grill, outside shower
Fridge, microwave, oven, stovetop
Serene beach cottage a short walk from beautiful Broadkill Beach. Pet friendly!

Cottage in Milton

Serene beach cottage a short walk from beautiful Broadkill Beach. Pet friendly!
9.8 out of 10, Exceptional, (28)
"Comfortable and close to the beach - perfect!"
United States
Saundra P.
The price is ￥19,623
￥58,195 total
includes taxes & fees
Dec 16 - Dec 17
Serene beach cottage a short walk from beautiful Broadkill Beach. Pet friendly!
1 bedroom, iron/ironing board, WiFi, bed sheets
Cozy Unit in Milford, Delaware -Close to DE Turf

Apartment in Milford

Cozy Unit in Milford, Delaware -Close to DE Turf
10.0 out of 10, Exceptional, (2)
"Perfect place for my son and I that had a lacrosse tourney that was only 8 minutes away at the Delaware turf fields Cat was awesome and replied very fast and was super accommodating!! "
United States
Shaine L.
The price is ￥18,472
￥35,008 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Cozy Unit in Milford, Delaware -Close to DE Turf
Pool
New 3‑BR Ranch by DE Turf & Beaches

Vacation Home in Lincoln

New 3‑BR Ranch by DE Turf & Beaches
10.0 out of 10, Exceptional, (3)
"Beautiful accommodations that are very comfortable. We would stay there again."
United States
Beth S.
The price is ￥19,468
￥42,187 total
includes taxes & fees
Dec 30 - Dec 31
New 3‑BR Ranch by DE Turf & Beaches
Outdoor dining
Poe Themed Home Close to Beaches and DE Turf

Vacation Home in Milford

Poe Themed Home Close to Beaches and DE Turf
9.6 out of 10, Exceptional, (5)
"Comfortable beds, meticulous details of EA Poe throughout, walking distance to adorable Dolce’ for coffee and pastries, and lovely Milford charm are a few of the outstanding qualities of this home away from home. "
United States
Linda I.
The price is ￥25,189
￥43,271 total
includes taxes & fees
Dec 14 - Dec 15
Poe Themed Home Close to Beaches and DE Turf
3 bedrooms, WiFi, bed sheets
Premier Host: 2nd Story Suite Historic Home, walk to Dogfish Head!

Vacation Home in Milton

Premier Host: 2nd Story Suite Historic Home, walk to Dogfish Head!
2.0 star property
The price is ￥11,320
￥20,382 total
includes taxes & fees
Dec 15 - Dec 16
Premier Host: 2nd Story Suite Historic Home, walk to Dogfish Head!
Dining
Delaware Beachfront Private Getaway on the Bay

Vacation Home in Milford

Delaware Beachfront Private Getaway on the Bay
9.8 out of 10, Exceptional, (193)
"Lovely place for us and our pets! It was so nice to just relax. It’s right on the beach and has a great fenced in yard for the pups!! They have just about thought of everything you need for a beach day and have it there in the shed for you to use. Was wonderful!!!!!Definitely would stay there again! "
United States
Shanna L.
The price is ￥28,467
￥80,612 total
includes taxes & fees
Dec 21 - Dec 22
Delaware Beachfront Private Getaway on the Bay
Fridge, microwave, oven, stovetop
Spacious 5 Bedroom w/Pool, Patio and Theater

Vacation Home in Magnolia

Spacious 5 Bedroom w/Pool, Patio and Theater
9.8 out of 10, Exceptional, (7)
"Great house for a large family "
United States
Stephanie
The price is ￥54,497
￥121,426 total
includes taxes & fees
Dec 22 - Dec 23
Spacious 5 Bedroom w/Pool, Patio and Theater
Terrace/patio
Lewes beach relax hot-tub games

Vacation Home in Lewes

Lewes beach relax hot-tub games
10.0 out of 10, Exceptional, (3)
"The house was excellent in nearly all regards."
United States
Andrew B.
The price is ￥87,222
￥188,017 total
includes taxes & fees
Dec 16 - Dec 17
Lewes beach relax hot-tub games
Fridge, microwave, oven, stovetop
Cozy home w/ amazing sunsets minutes to DE/MD Beaches: Come enjoy! 4 BR 3 BATH

Vacation Home in Lewes

Cozy home w/ amazing sunsets minutes to DE/MD Beaches: Come enjoy! 4 BR 3 BATH
8.8 out of 10, Excellent, (17)
"This home is beautiful and clean and perfectly located for us to take advantage of the beaches as well as the baseball tournament that our grandson was in. The Host was very responsive and we thoroughly enjoyed our stay here."
United States
Carol H.
The price is ￥62,196
￥108,532 total
includes taxes & fees
Dec 13 - Dec 14
Cozy home w/ amazing sunsets minutes to DE/MD Beaches: Come enjoy! 4 BR 3 BATH
Property grounds
Adorable two-bedroom retreat close to Easton, Denton, Centreville

Vacation Home in Queen Anne

Adorable two-bedroom retreat close to Easton, Denton, Centreville
10.0 out of 10, Exceptional, (26)
"Quiet, quaint....perfect"
United States
Catherine M.
The price is ￥29,388
￥55,709 total
includes taxes & fees
Dec 22 - Dec 23
Adorable two-bedroom retreat close to Easton, Denton, Centreville
WiFi, bed sheets
Welcoming 3-bedroom house with AC in charming Milford.

Vacation Home in Milford

Welcoming 3-bedroom house with AC in charming Milford.
2.0 star property
The price is ￥50,616
￥77,501 total
includes taxes & fees
Dec 18 - Dec 19
Welcoming 3-bedroom house with AC in charming Milford.
Exterior
Come Be Our Guest At A Place of Peace

Vacation Home in Harbeson

Come Be Our Guest At A Place of Peace
The price is ￥27,988
￥44,330 total
includes taxes & fees
Dec 13 - Dec 14
Come Be Our Guest At A Place of Peace
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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Top Greenwood Hotel Reviews

Hyatt House Lewes/Rehoboth Beach

Hyatt House Lewes/Rehoboth Beach

10/10 Excellent
"Everything was beautiful as my husband and I walked in. We were very impressed with the clean look. The room was larger then other places we have stayed at. The TV also was larger. Very friendly staff at desk "
IRIS 1-night trip
Posted 2 days ago
Hyatt House Lewes/Rehoboth Beach

Find out more about Greenwood

Search for holiday rentals in Greenwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Greenwood using one of the methods below:

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Look no further and take a look at our great range of rental properties in Greenwood!

Frequently asked questions

Can I find a vacation rental in Greenwood?

Yes, there are vacation rentals near popular local attractions in Greenwood, or you can choose a secluded option if you'd like a relaxing place to stay. Greenwood is known for its restaurants and sporting events. Make sure you have time to check out the shopping and beaches during your trip.

What are some of the best vacation rentals that Greenwood has to offer?

Bayfront Cottage with Spectacular Views: Visitors like this Greenwood vacation home rental. It is located on the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

What can I see and do in Greenwood?

Explore the area and family-friendly sights such as Delaware State Fairgrounds, or get out into nature at a spot like DE Turf Sports Complex. Harrington Raceway and Casino and Second Street Players - Riverfront Theatre are a couple of places you'll find in the larger area.

What are vacation rentals like in Greenwood?

Vacation rentals are private accommodations you can stay in for a few days or a quick weekend in Greenwood. Vacation rentals offer extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a small group gathering.