Greenwood Holiday Rentals

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Our top choices for Greenwood holiday rentals

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

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 NZ$646
includes taxes & fees
23 Dec - 24 Dec
Serene beach cottage a short walk from beautiful Broadkill Beach. Pet friendly!

The Little house W/ Pool & Spa

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 NZ$361
includes taxes & fees
30 Dec - 31 Dec
The Little house W/ Pool & Spa

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

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 NZ$695
includes taxes & fees
11 Jan - 12 Jan 2026
Spacious Home-Steps Away From Quiet Beach-Nature and Wildlife-Pet Friendly!

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

Historic home, great yard & Walk to Dogfish Head Brewery!
Milton
9.8 out of 10, Exceptional, (9)
"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 NZ$245
includes taxes & fees
14 Jan - 15 Jan 2026
Historic home, great yard & Walk to Dogfish Head Brewery!

Elegant 3-Bedroom Condo in Lewes with Pond Views

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 NZ$433
includes taxes & fees
7 Jan - 8 Jan 2026
Elegant 3-Bedroom Condo in Lewes with Pond Views

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

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 NZ$598
includes taxes & fees
17 Dec - 18 Dec
Pets Friendly, Waterfront, Large backyard, Bonfire with grill, outside shower

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

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 NZ$337
includes taxes & fees
17 Dec - 18 Dec
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

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

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 NZ$503
includes taxes & fees
19 Dec - 20 Dec
1st Floor Beach-town Condo. We are Pet Friendly!

Poe Themed Home Close to Beaches and DE Turf

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 NZ$481
includes taxes & fees
19 Dec - 20 Dec
Poe Themed Home Close to Beaches and DE Turf

Lewes Beach town Condo on 1st Floor!

Lewes Beach town Condo on 1st Floor!
Villages of Five Points
10.0 out of 10, Exceptional, (21)
"We had a great stay. The place was prefect! "
United States
Lisa S.
Lewes Beach town Condo on 1st Floor!

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

Specious & Cozy. Close to Lewes and Rehoboth Beaches. Community Pool
Lewes
10.0 out of 10, Exceptional, (3)
"We thoroughly enjoyed our stay"
United States
Jonathan D.
The price is NZ$462
includes taxes & fees
17 Dec - 18 Dec
Specious & Cozy. Close to Lewes and Rehoboth Beaches. Community Pool

Adorable two-bedroom retreat close to Easton, Denton, Centreville

Adorable two-bedroom retreat close to Easton, Denton, Centreville
Queen Anne
10.0 out of 10, Exceptional, (26)
"Quiet, quaint....perfect"
United States
Catherine M.
Adorable two-bedroom retreat close to Easton, Denton, Centreville

Cozy Unit in Milford, Delaware -Close to DE Turf

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 NZ$393
includes taxes & fees
30 Dec - 31 Dec
Cozy Unit in Milford, Delaware -Close to DE Turf

Delaware Beachfront Private Getaway on the Bay

Delaware Beachfront Private Getaway on the Bay
Milford
9.8 out of 10, Exceptional, (193)
"All our cares slipped away as we pulled into the driveway to this beachfront retreat. Comfortable, clean and cozy rooms provided great sleep and room to relax. The proximity to the water was convenient and effortless. I look forward to staying there again. "
United States
Debbie T.
The price is NZ$922
includes taxes & fees
17 Dec - 18 Dec
Delaware Beachfront Private Getaway on the Bay

New 3‑BR Ranch by DE Turf & Beaches

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 NZ$468
includes taxes & fees
30 Dec - 31 Dec
New 3‑BR Ranch by DE Turf & Beaches

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

Premier Host: 2nd Story Suite Historic Home, walk to Dogfish Head!
2.0 star property
Milton
The price is NZ$227
includes taxes & fees
17 Dec - 18 Dec
Premier Host: 2nd Story Suite Historic Home, walk to Dogfish Head!

Come Be Our Guest At A Place of Peace

Come Be Our Guest At A Place of Peace
Harbeson
The price is NZ$496
includes taxes & fees
19 Dec - 20 Dec
Come Be Our Guest At A Place of Peace

Turnbridge Manor

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 NZ$1,123
includes taxes & fees
30 Dec - 31 Dec
Turnbridge Manor

Spacious 5 Bedroom w/Pool, Patio and Theater

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 NZ$1,342
includes taxes & fees
22 Dec - 23 Dec
Spacious 5 Bedroom w/Pool, Patio and Theater

Lewes beach relax hot-tub games

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 NZ$2,222
includes taxes & fees
11 Jan - 12 Jan 2026
Lewes beach relax hot-tub games
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 favorite 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 depends 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 NZ$245 per night. Entering your travel dates in the search wizard you might find 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?

Bayfront Cottage with Spectacular Views: This holiday home rental outside of Greenwood is located on the beach, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 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.