A swamp with tall trees and water reflecting the greenery.

Greenwood Vacation Rentals

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Our top choices for Greenwood vacation rentals

1. Pet-Friendly Pond Cottage • Nature Escape Near Beaches

Pet-Friendly Pond Cottage • Nature Escape Near Beaches
Seaford
The price is CA $179
CA $219 total
includes taxes & fees
Sep 21 - Sep 22
Pet-Friendly Pond Cottage • Nature Escape Near Beaches

2. Pool • Bike Trail • Minutes to Lewes Beach

Pool • Bike Trail • Minutes to Lewes Beach
Lewes
The price is CA $254
CA $560 total
includes taxes & fees
Sep 22 - Sep 23
Pool • Bike Trail • Minutes to Lewes Beach

3. 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, (1 review)
"Thank you, we had a very pleasant stay"
United States
andy O.
The price is CA $237
CA $397 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape

4. 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, (59 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 CA $156
CA $315 total
includes taxes & fees
Sep 2 - Sep 3
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

5. 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 CA $164
CA $312 total
includes taxes & fees
Aug 27 - Aug 28
Cozy Unit in Milford, Delaware -Close to DE Turf

6. 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 CA $131
CA $495 total
includes taxes & fees
Sep 2 - Sep 3
Luxury 2 bedroom Apt. Near DE Turf & Beaches!

7. 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 CA $111
CA $278 total
includes taxes & fees
Aug 27 - Aug 28
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

8. 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, (15 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 CA $224
CA $381 total
includes taxes & fees
Aug 27 - Aug 28
Poe Themed Home Close to Beaches and DE Turf

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 CA $114
CA $262 total
includes taxes & fees
Sep 2 - Sep 3
Tiny house w/ Pool on water near Beaches / turf

10. 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 CA $199
CA $453 total
includes taxes & fees
Sep 8 - Sep 9
Getaway on 1/2 Acre w/ Deck in Georgetown

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

Getaway on 1/2 Acre w/ Deck in Georgetown
Georgetown
10.0 out of 10, Exceptional, (8 reviews)
"Fantastic experience! The home was clean and well stocked."
United States
June T.
The price is CA $144
CA $466 total
includes taxes & fees
Sep 8 - Sep 9
Getaway on 1/2 Acre w/ Deck in Georgetown

12. 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 CA $145
CA $299 total
includes taxes & fees
Sep 2 - Sep 3
Waterfront studio w/ pool - shopping and beaches

13. 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 CA $188
CA $438 total
includes taxes & fees
Sep 2 - Sep 3
New 3‑BR Ranch by DE Turf & Beaches

14. The Little house W/ Pool & Spa

The Little house W/ Pool & Spa
Lincoln
9.8 out of 10, Exceptional, (6 reviews)
"The host was very welcoming. The house was very nice."
United States
Lisa H.
The price is CA $151
CA $435 total
includes taxes & fees
Sep 15 - Sep 16
The Little house W/ Pool & Spa

15. Cozy Room in Dover

Cozy Room in Dover
Dover
The price is CA $81
CA $133 total
includes taxes & fees
Aug 31 - Sep 1
Cozy Room in Dover

16. Cozy home minutes from Lewes and Rehoboth Beach

Cozy home minutes from Lewes and Rehoboth Beach
Milton
10.0 out of 10, Exceptional, (40 reviews)
"All went well.. keep doing a great job!We had a great stay"
United States
Deb W.
The price is CA $249
CA $444 total
includes taxes & fees
Aug 29 - Aug 30
Cozy home minutes from Lewes and Rehoboth Beach

17. 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
9.0 out of 10, Wonderful, (7 reviews)
The price is CA $227
CA $386 total
includes taxes & fees
Aug 27 - Aug 28
Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!

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

Pool • Private Wooded Deck • Mins. to Lewes Beach
Lewes
8.8 out of 10, Excellent, (5 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 CA $167
CA $456 total
includes taxes & fees
Sep 1 - Sep 2
Pool • Private Wooded Deck • Mins. to Lewes Beach

19. Spacious Condo•Pond Views•Centrally located

Spacious Condo•Pond Views•Centrally located
Plantations East
9.8 out of 10, Exceptional, (39 reviews)
"Great set up and plenty of room and parking! Host was easy to communicate with and they were very quick to reply. I would definitely stay there again in the future. "
United States
Jennifer B.
The price is CA $174
CA $482 total
includes taxes & fees
Sep 21 - Sep 22
Spacious Condo•Pond Views•Centrally located

20. 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, (34 reviews)
"Easy booking and check in process- clean and lovely property exactly as advertised. Would book again if we come back to the area! "
United States
Cassandra P.
Coastal Cottage 15 Minutes to Lewes Beach + Bike Trail Access.
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a vacation rental in Greenwood?

Yes, there are vacation rentals near popular local attractions in Greenwood, or you can choose a secluded option if you'd like a relaxing place to 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 vacation rentals that Greenwood has to offer?

Gorgeous pano views, Beach Front Access and hot tub! Your peaceful escape! : Visitors like this Greenwood vacation home rental. It is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

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 larger area.

What are vacation rentals like in Greenwood?

Vacation rentals are private accommodations you can stay in for a few days or a quick weekend in Greenwood. Vacation rentals offer extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a small group gathering.