A swamp with tall trees and water reflecting the greenery.

Greenwood Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Greenwood holiday rentals

A wooden cabin with a porch, a rocking chair, and a table.

1. Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape

Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
Lincoln
10.0 out of 10, Exceptional, (2 reviews)
"Thank you, we had a very pleasant stay"
United States
andy O.
The price is AU$433
includes taxes & fees
28 Oct - 29 Oct
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
A bedroom with a bed, a dresser, a mirror, and a door leading to another room.

2. Cozy Unit in Milford, Delaware -Close to DE Turf

Cozy Unit in Milford, Delaware -Close to DE Turf
Milford
9.6 out of 10, Exceptional, (4 reviews)
"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$326
includes taxes & fees
19 Oct - 20 Oct
Cozy Unit in Milford, Delaware -Close to DE Turf
A patio area with outdoor seating, string lights, and potted plants.

3. Poe Themed Home Close to Beaches and DE Turf

Poe Themed Home Close to Beaches and DE Turf
Milford
8.6 out of 10, Excellent, (17 reviews)
"The owner thought of many amenities that I haven't seen before like breakfast bars and oatmeal packets. Very much appreciated."
United States
Sharon
The price is AU$391
includes taxes & fees
16 Oct - 17 Oct
Poe Themed Home Close to Beaches and DE Turf
A modern living space with a dining area, sofa, and kitchen.

4. Luxury 2 bedroom Apt. Near DE Turf & Beaches!

Luxury 2 bedroom Apt. Near DE Turf & Beaches!
Milford
10.0 out of 10, Exceptional, (1 review)
"This property was perfect for our family while at a lacrosse tournament. It was close to the field and very comfortable. Having two full bathrooms to get ready for the day was a treat! The property was clean and spacious. Also, the host was also extremely responsive. We will definitely return."
United States
Jill M.
The price is AU$472
includes taxes & fees
19 Oct - 20 Oct
Luxury 2 bedroom Apt. Near DE Turf & Beaches!
A bedroom with a bunk bed, a single bed, a desk, and a chair.

5. Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Frederica
9.6 out of 10, Exceptional, (25 reviews)
"We enjoy this place!!!"
United States
nahum f.
The price is AU$309
includes taxes & fees
28 Oct - 29 Oct
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
A two-story house with a front porch, a driveway, and a landscaped garden with various plants and a small tree.

6. 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, (63 reviews)
"The suite was very clean and our two children greatly enjoyed the pool!"
United States
Kay Lorelle R.
The price is AU$312
includes taxes & fees
21 Oct - 22 Oct
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
Pool

7. Waterfront studio w/ pool - shopping and beaches

Waterfront studio w/ pool - shopping and beaches
Lincoln
10.0 out of 10, Exceptional, (1 review)
"Location was great for our needs. Left feeling refreshed and happy. The decor is uplifting. Beds very comfortable. Thanks for the offering!"
United States
Paula R.
The price is AU$294
includes taxes & fees
20 Oct - 21 Oct
Waterfront studio w/ pool - shopping and beaches
Pool

8. The Little house W/ Pool & Spa

The Little house W/ Pool & Spa
Lincoln
9.8 out of 10, Exceptional, (6 reviews)
"Host was very helpful and has great communication. Beautiful place to stay!"
United States
veronica d.
The price is AU$447
includes taxes & fees
18 Oct - 19 Oct
The Little house W/ Pool & Spa
Pool

9. Tiny house w/ Pool on water near Beaches / turf

Tiny house w/ Pool on water near Beaches / turf
Lincoln
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful tiny home with lavish pool in a quiet neighborhood. Loved the area, the home, and amenities provided. Although, we did not receive the code to unlock the door at check in time and host did not answer our text for about 40 minutes. Thankfully the housecleaner was there to let us in! Still a great stay. "
United States
Jessica W.
The price is AU$274
includes taxes & fees
18 Oct - 19 Oct
Tiny house w/ Pool on water near Beaches / turf
Pool

10. New 3‑BR Ranch by DE Turf & Beaches

New 3‑BR Ranch by DE Turf & Beaches
Lincoln
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful accommodations that are very comfortable. We would stay there again."
United States
Beth S.
The price is AU$412
includes taxes & fees
19 Oct - 20 Oct
New 3‑BR Ranch by DE Turf & Beaches
A covered patio with a table and chairs, a white fence, and a view of the greenery.

11. Getaway on 1/2 Acre w/ Deck in Georgetown

Getaway on 1/2 Acre w/ Deck in Georgetown
3.0 star property
Georgetown
10.0 out of 10, Exceptional, (1 review)
"This place is just as you see in the photos; clean, welcoming, great location, and very peaceful. We are certainly looking forward to staying here next year, if available. The contact person was available and answered quickly when I contacted him. "
United States
ANA
The price is AU$478
includes taxes & fees
9 Nov - 10 Nov
Getaway on 1/2 Acre w/ Deck in Georgetown
A room with a large window overlooking a river, a wicker chair, and a glass table.

12. Spacious Condo•Pond Views•Centrally located

Spacious Condo•Pond Views•Centrally located
Plantations East
9.6 out of 10, Exceptional, (42 reviews)
"This place is a great central location to everywhere we wanted to go! The whole living room area was a great space for everyone to get together and hang out. The enclosed patio is also great for playing games and relaxing. Communication was also very good and we enjoyed our stay!"
United States
Bianca S.
The price is AU$392
includes taxes & fees
25 Oct - 26 Oct
Spacious Condo•Pond Views•Centrally located
A modern kitchen with a central island, stainless steel appliances, and a dining area with a chandelier.

13. Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!

Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!
Milford
9.4 out of 10, Exceptional, (12 reviews)
"Awesome property! Great price! Excellent communication!"
United States
Krista L.
The price is AU$452
includes taxes & fees
19 Oct - 20 Oct
Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!
A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

14. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful home. Plenty of space inside with great outdoor spaces. Very clean and easy to contact host. Family friendly-would highly recommend!"
United States
Jessica H.
The price is AU$852
includes taxes & fees
27 Oct - 28 Oct
Turnbridge Manor
A living room with a leather sofa, a coffee table with a plant, a TV on the wall, and a kitchen in the background.

15. Lewes Beach town Condo on 1st Floor!

Lewes Beach town Condo on 1st Floor!
Villages of Five Points
10.0 out of 10, Exceptional, (28 reviews)
"We had a great stay. The place was prefect! "
United States
Lisa S.
Lewes Beach town Condo on 1st Floor!
A modern living room with a flat-screen TV, grey sofa, and a dining area with a white table and chairs.

16. 1st Floor Beach-town Condo. We are Pet Friendly!

1st Floor Beach-town Condo. We are Pet Friendly!
Villages of Five Points
9.8 out of 10, Exceptional, (45 reviews)
"Fantastic stay!!!! Very safe, extremely pet friendly for our senior dog - 1000% recommend "
United States
Mandy M.
The price is AU$463
includes taxes & fees
4 Nov - 5 Nov
1st Floor Beach-town Condo. We are Pet Friendly!
A modern kitchen with a large island, bar stools, and pendant lighting.

17. Spacious 5 Bedroom w/Pool, Patio and Theater

Spacious 5 Bedroom w/Pool, Patio and Theater
Magnolia
9.2 out of 10, Wonderful, (12 reviews)
"The host was very accommodating and the house was excellent and served our needs perfectly."
United States
John K.
Spacious 5 Bedroom w/Pool, Patio and Theater
A spacious living area with a large sofa, a dining table, and a kitchen with white cabinets and a wooden countertop.

18. Coastal Cottage 15 Minutes to Lewes Beach + Bike Trail Access.

Coastal Cottage 15 Minutes to Lewes Beach + Bike Trail Access.
Milton
10.0 out of 10, Exceptional, (37 reviews)
"Great location, beautiful house, perfect for our kids and dogs!"
United States
Alexis P.
Coastal Cottage 15 Minutes to Lewes Beach + Bike Trail Access.
A round window with a view of a garden, a tree, and a building in the background.

19. Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5

Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
Kitts Hummock
10.0 out of 10, Exceptional, (1 review)
"Our time here was an attraction in itself. There were so many small details. I won't mention all of them as I don't want to spoil the surprise but one of our favorites was a telescope pointed towards an ocean piling where birds frequently perch. The house felt interactive and playful. There were snacks and beverage options (including tea, coffee, water, and even other surprises) available. Very clean. One consideration is the stairscase. I would advise caution for those with mobility issues (bad...
United States
Alex L.
The price is AU$530
includes taxes & fees
18 Oct - 19 Oct
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
A kitchen with white cabinets, a granite countertop, a stainless steel refrigerator, a microwave, and a stove.

20. 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, (38 reviews)
"Love how pet friendly it was a so close to the beach!"
United States
Lauren B.
The price is AU$611
includes taxes & fees
11 Nov - 12 Nov
Serene beach cottage a short walk from beautiful Broadkill Beach. Pet friendly!
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

Home2 Suites by Hilton Lewes Rehoboth Beach

Home2 Suites by Hilton Lewes Rehoboth Beach

10/10 Excellent
"The staff is always friendly but appreciate that it is pet-friendly, especially with the fenced in play area. And, always pristine in cleanliness, very roomy accommodations."
Miya 2-night trip
Posted 7 hours ago
Home2 Suites by Hilton Lewes Rehoboth Beach

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$312 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?

Bay Front Water & Beach Front Broadkill Pet Friendly Sleeps 12 4Bed 4Bath 4Floor: This holiday home rental outside of Greenwood is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

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 Killens Pond State Park 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.