Greenwood Holiday Rentals

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Holiday Rentals in Greenwood

Holiday Home in Milton

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 HK$469
HK$919 total
includes taxes & fees
7 Dec - 8 Dec
Historic home, great yard & Walk to Dogfish Head Brewery!

Holiday Home in Georgetown

9.8 out of 10, Exceptional, (47)
"Very thoughtful and hospitable hosts. We had a lovely time!"
United States
Eve S.
The price is HK$701
HK$1,518 total
includes taxes & fees
8 Dec - 9 Dec
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

Cottage in Milton

9.8 out of 10, Exceptional, (28)
"Comfortable and close to the beach - perfect!"
United States
Saundra P.
The price is HK$981
HK$2,908 total
includes taxes & fees
9 Dec - 10 Dec
Serene beach cottage a short walk from beautiful Broadkill Beach. Pet friendly!

Mobile Home in Lincoln

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 HK$654
HK$1,711 total
includes taxes & fees
30 Dec - 31 Dec
The Little house W/ Pool & Spa

Condo in Villages of Five Points

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 HK$609
HK$2,108 total
includes taxes & fees
10 Dec - 11 Dec
1st Floor Beach-town Condo. We are Pet Friendly!

Condo in Plantations East

9.8 out of 10, Exceptional, (20)
"Amazing location!!!!"
United States
Tania W.
The price is HK$595
HK$2,015 total
includes taxes & fees
15 Dec - 16 Dec
Elegant 3-Bedroom Condo in Lewes with Pond Views

Holiday Home in Milton

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 HK$1,168
HK$2,691 total
includes taxes & fees
16 Dec - 17 Dec
Pets Friendly, Waterfront, Large backyard, Bonfire with grill, outside shower

Holiday Home in Milford

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 HK$1,044
HK$2,765 total
includes taxes & fees
15 Dec - 16 Dec
Spacious Home-Steps Away From Quiet Beach-Nature and Wildlife-Pet Friendly!

Apartment in Lewes

10.0 out of 10, Exceptional, (2)
"Great condo. Fantastic pool. Close to nice Family Beach."
United States
Mary K.
The price is HK$778
HK$2,121 total
includes taxes & fees
7 Dec - 8 Dec
Specious & Cozy. Close to Lewes and Rehoboth Beaches. Community Pool

Apartment in Milford

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 HK$925
HK$1,760 total
includes taxes & fees
6 Dec - 7 Dec
Cozy Unit in Milford, Delaware -Close to DE Turf

Holiday Home in Lewes

10.0 out of 10, Exceptional, (3)
"The house was excellent in nearly all regards."
United States
Andrew B.
The price is HK$3,956
HK$8,847 total
includes taxes & fees
9 Dec - 10 Dec
Lewes beach relax hot-tub games

Holiday Home in Milford

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 HK$1,261
HK$2,166 total
includes taxes & fees
8 Dec - 9 Dec
Poe Themed Home Close to Beaches and DE Turf

Holiday Home in Milton

2.0 star property
The price is HK$567
HK$1,020 total
includes taxes & fees
9 Dec - 10 Dec
Premier Host: 2nd Story Suite Historic Home, walk to Dogfish Head!

Holiday Home in Milford

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 HK$1,425
HK$4,129 total
includes taxes & fees
6 Dec - 7 Dec
Delaware Beachfront Private Getaway on the Bay

Holiday Home in Lincoln

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 HK$973
HK$2,124 total
includes taxes & fees
10 Dec - 11 Dec
New 3‑BR Ranch by DE Turf & Beaches

Holiday Home in Harbeson

The price is HK$1,401
HK$2,126 total
includes taxes & fees
12 Dec - 13 Dec
Come Be Our Guest At A Place of Peace

Holiday Home in Denton

9.8 out of 10, Exceptional, (12)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is HK$3,113
HK$5,115 total
includes taxes & fees
31 Dec - 1 Jan 2026
Turnbridge Manor

Holiday Home in Milton

2.0 star property
The price is HK$1,308
HK$4,067 total
includes taxes & fees
7 Dec - 8 Dec
Mid-Century Milton w/Pool, Pond, and Bike Trails!

Holiday Home in Lewes

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 HK$2,958
HK$5,262 total
includes taxes & fees
5 Dec - 6 Dec
Cozy home w/ amazing sunsets minutes to DE/MD Beaches: Come enjoy! 4 BR 3 BATH

Holiday Home in Magnolia

9.8 out of 10, Exceptional, (7)
"Great house for a large family "
United States
Stephanie
The price is HK$3,169
HK$6,674 total
includes taxes & fees
30 Dec - 31 Dec
Spacious 5 Bedroom w/Pool, Patio and Theater
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

Find out more about Greenwood

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Frequently asked questions

Can I find a holiday rental in Greenwood?

Yes, there are holiday rentals close to the most popular sights in Greenwood, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Greenwood has to offer?

Captain's Quarters: This holiday home rental outside of Greenwood is located near the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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 Delaware Technical Community College Georgetown Campus are a couple of places you'll find in the wider area.

What are holiday rentals like in Greenwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Greenwood. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for a small group gathering.