A swamp with tall trees and water reflecting the greenery.

Greenwood Holiday Rentals

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Our top choices for Greenwood holiday rentals

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 NZ$528
includes taxes & fees
24 Sept - 25 Sept
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape

2. 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, (16 reviews)
"Theme decor was awesome. Location was a quick stroll downtown. Very busy street so use a white noise app on your phone if street noise is an issue."
United States
Dee Z. B.
The price is NZ$472
includes taxes & fees
23 Oct - 24 Oct
Poe Themed Home Close to Beaches and DE Turf

3. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is NZ$1,036
includes taxes & fees
30 Sept - 1 Oct
Turnbridge Manor

4. 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, (3 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 NZ$393
includes taxes & fees
24 Sept - 25 Sept
Cozy Unit in Milford, Delaware -Close to DE Turf

5. Walk to Bowers Beach! Peaceful Coastal Retreat

Walk to Bowers Beach! Peaceful Coastal Retreat
3.0 star property
Frederica
The price is NZ$1,278
includes taxes & fees
4 Oct - 5 Oct
Walk to Bowers Beach! Peaceful Coastal Retreat

6. 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 NZ$541
includes taxes & fees
29 Sept - 30 Sept
The Little house W/ Pool & Spa

7. Come stay at our beautiful 3 bedroom home located in rural Milford De.

Come stay at our beautiful 3 bedroom home located in rural Milford De.
Milford
10.0 out of 10, Exceptional, (6 reviews)
"The guys went to the race and they were very happy with the location the price and the people were very nice to deal with"
United States
debra h.
The price is NZ$837
includes taxes & fees
24 Oct - 25 Oct
Come stay at our beautiful 3 bedroom home located in rural Milford De.

8. 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 NZ$530
includes taxes & fees
28 Sept - 29 Sept
New 3‑BR Ranch by DE Turf & Beaches

9. 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
9.2 out of 10, Wonderful, (9 reviews)
"Awesome property! Great price! Excellent communication!"
United States
Krista L.
Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!

10. Escape to our spacious & serene 3-bedroom home with stunning bay views.

Escape to our spacious & serene 3-bedroom home with stunning bay views.
Milford
9.6 out of 10, Exceptional, (24 reviews)
"We had a great time! Very short walk to the beach. Good communication with the owner. Pet-friendly. Would love to stay here again! "
United States
Dannah D.
The price is NZ$865
includes taxes & fees
29 Sept - 30 Sept
Escape to our spacious & serene 3-bedroom home with stunning bay views.

11. 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 NZ$338
includes taxes & fees
21 Oct - 22 Oct
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

12. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"My son and I had a great stay here for the weekend, camper was clean and had everything we needed and the family was happy to join us or let us have our privacy. All you could ask for and the backyard pool area is as good as it looks in the pictures. Would go back anytime we are in the area."
United States
Robert N.
The price is NZ$448
includes taxes & fees
29 Sept - 30 Sept
Mini Aruba RV/Glamping Tent

13. 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 NZ$378
includes taxes & fees
29 Sept - 30 Sept
Waterfront studio w/ pool - shopping and beaches

14. 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, (62 reviews)
"We stayed at this property for 6 nights, everything was exactly like the pictures and very clean. We were just far enough to many shopping areas and grocery stores. It was very quiet and peaceful. Ed and Cindy are amazing hosts, we will be returning next year!"
United States
Haileigh
The price is NZ$367
includes taxes & fees
16 Oct - 17 Oct
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

15. 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 NZ$569
includes taxes & fees
24 Sept - 25 Sept
Luxury 2 bedroom Apt. Near DE Turf & Beaches!

16. 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 NZ$331
includes taxes & fees
24 Sept - 25 Sept
Tiny house w/ Pool on water near Beaches / turf

17. Walk to Bowers Beach! Peaceful Coastal Retreat

Walk to Bowers Beach! Peaceful Coastal Retreat
Frederica
The price is NZ$1,302
includes taxes & fees
24 Sept - 25 Sept
Walk to Bowers Beach! Peaceful Coastal Retreat

18. Lewes Beach town Condo on 1st Floor!

Lewes Beach town Condo on 1st Floor!
Villages of Five Points
10.0 out of 10, Exceptional, (26 reviews)
"We had a great stay. The place was prefect! "
United States
Lisa S.
The price is NZ$688
includes taxes & fees
3 Oct - 4 Oct
Lewes Beach town Condo on 1st Floor!

19. 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 NZ$818
includes taxes & fees
19 Oct - 20 Oct
Serene beach cottage a short walk from beautiful Broadkill Beach. Pet friendly!

20. Pool • Private Wooded Deck • Mins. to Lewes Beach

Pool • Private Wooded Deck • Mins. to Lewes Beach
Lewes
9.2 out of 10, Wonderful, (7 reviews)
"This is NOT a three bedroom property!!!!!! There are two (2) bedrooms upstairs and a small sleeper-loveseat (that was broken) located on the first floor, in the back room which leads to the rear deck. The host refused to contact me via cell phone, when I discovered this problem upon my arrival. His emails were rude and his attitude was poor overall."
United States
Anthony
The price is NZ$617
includes taxes & fees
1 Oct - 2 Oct
Pool • Private Wooded Deck • Mins. to Lewes Beach
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Greenwood holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Greenwood. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Greenwood. Seeing all the best attractions is bound to make you fall in love with Greenwood. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Greenwood short-term rentals, that won’t be hard to do.

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 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.