Greenwood Holiday Rentals

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Holiday Rentals in Greenwood

Historic home, great yard & Walk to Dogfish Head Brewery!

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 AU$183
includes taxes & fees
7 Dec - 8 Dec
Historic home, great yard & Walk to Dogfish Head Brewery!

EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

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 AU$297
includes taxes & fees
14 Dec - 15 Dec
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

Serene beach cottage a short walk from beautiful Broadkill Beach. Pet friendly!

Milton
9.8 out of 10, Exceptional, (28)
"Comfortable and close to the beach - perfect!"
United States
Saundra P.
The price is AU$572
includes taxes & fees
9 Dec - 10 Dec
Serene beach cottage a short walk from beautiful Broadkill Beach. Pet friendly!

The Little house W/ Pool & Spa

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 AU$338
includes taxes & fees
30 Dec - 31 Dec
The Little house W/ Pool & Spa

1st Floor Beach-town Condo. We are Pet Friendly!

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 AU$414
includes taxes & fees
10 Dec - 11 Dec
1st Floor Beach-town Condo. We are Pet Friendly!

Elegant 3-Bedroom Condo in Lewes with Pond Views

Plantations East
9.8 out of 10, Exceptional, (20)
"Amazing location!!!!"
United States
Tania W.
The price is AU$395
includes taxes & fees
9 Dec - 10 Dec
Elegant 3-Bedroom Condo in Lewes with Pond Views

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

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 AU$529
includes taxes & fees
11 Dec - 12 Dec
Pets Friendly, Waterfront, Large backyard, Bonfire with grill, outside shower

Spacious Home-Steps Away From Quiet Beach-Nature and Wildlife-Pet Friendly!

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 AU$542
includes taxes & fees
15 Dec - 16 Dec
Spacious Home-Steps Away From Quiet Beach-Nature and Wildlife-Pet Friendly!

Specious & Cozy. Close to Lewes and Rehoboth Beaches. Community Pool

Lewes
10.0 out of 10, Exceptional, (2)
"Great condo. Fantastic pool. Close to nice Family Beach."
United States
Mary K.
The price is AU$418
includes taxes & fees
7 Dec - 8 Dec
Specious & Cozy. Close to Lewes and Rehoboth Beaches. Community Pool

Cozy Unit in Milford, Delaware -Close to DE Turf

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 AU$348
includes taxes & fees
16 Dec - 17 Dec
Cozy Unit in Milford, Delaware -Close to DE Turf

Lewes beach relax hot-tub games

Lewes
10.0 out of 10, Exceptional, (3)
"The house was excellent in nearly all regards."
United States
Andrew B.
The price is AU$1,837
includes taxes & fees
17 Dec - 18 Dec
Lewes beach relax hot-tub games

Poe Themed Home Close to Beaches and DE Turf

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 AU$425
includes taxes & fees
5 Dec - 6 Dec
Poe Themed Home Close to Beaches and DE Turf

Premier Host: 2nd Story Suite Historic Home, walk to Dogfish Head!

2.0 star property
Milton
The price is AU$202
includes taxes & fees
16 Dec - 17 Dec
Premier Host: 2nd Story Suite Historic Home, walk to Dogfish Head!

Delaware Beachfront Private Getaway on the Bay

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 AU$814
includes taxes & fees
14 Dec - 15 Dec
Delaware Beachfront Private Getaway on the Bay

New 3‑BR Ranch by DE Turf & Beaches

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 AU$413
includes taxes & fees
8 Dec - 9 Dec
New 3‑BR Ranch by DE Turf & Beaches

Come Be Our Guest At A Place of Peace

Harbeson
The price is AU$440
includes taxes & fees
5 Dec - 6 Dec
Come Be Our Guest At A Place of Peace

Turnbridge Manor

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 AU$937
includes taxes & fees
10 Dec - 11 Dec
Turnbridge Manor

Mid-Century Milton w/Pool, Pond, and Bike Trails!

2.0 star property
Milton
The price is AU$801
includes taxes & fees
7 Dec - 8 Dec
Mid-Century Milton w/Pool, Pond, and Bike Trails!

Cozy home w/ amazing sunsets minutes to DE/MD Beaches: Come enjoy! 4 BR 3 BATH

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 AU$1,072
includes taxes & fees
17 Dec - 18 Dec
Cozy home w/ amazing sunsets minutes to DE/MD Beaches: Come enjoy! 4 BR 3 BATH

Spacious 5 Bedroom w/Pool, Patio and Theater

Magnolia
9.8 out of 10, Exceptional, (7)
"Great house for a large family "
United States
Stephanie
The price is AU$1,294
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

Everything you need to know about Greenwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Greenwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greenwood holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Greenwood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenwood. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greenwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenwood holiday rentals we have selected for you start as low as AU$183 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Greenwood rentals

At Expedia, we put the best Greenwood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Greenwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greenwood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greenwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.