A swamp with tall trees and water reflecting the greenery.

Greenwood Vacation Rentals

Check prices for these dates

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

Our top choices for Greenwood vacation 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.
$301 nightly
The price is $310
Oct 25 - Oct 26
Total with taxes and fees
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.
$219 nightly
The price is $224
Oct 14 - Oct 15
Total with taxes and fees
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
$268 nightly
The price is $275
Oct 14 - Oct 15
Total with taxes and fees
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.
$311 nightly
The price is $331
Oct 15 - Oct 16
Total with taxes and fees
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.
$209 nightly
The price is $213
Oct 28 - Oct 29
Total with taxes and fees
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.
$212 nightly
The price is $216
Oct 21 - Oct 22
Total with taxes and fees
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.
$197 nightly
The price is $210
Oct 20 - Oct 21
Total with taxes and fees
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.
$294 nightly
The price is $313
Oct 14 - Oct 15
Total with taxes and fees
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.
$181 nightly
The price is $192
Oct 14 - Oct 15
Total with taxes and fees
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.
$278 nightly
The price is $297
Oct 19 - Oct 20
Total with taxes and fees
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
$334 nightly
The price is $334
Nov 9 - Nov 10
Total with taxes and fees
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.
$283 nightly
The price is $286
Oct 25 - Oct 26
Total with taxes and fees
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.
$317 nightly
The price is $326
Oct 14 - Oct 15
Total with taxes and fees
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.
$575 nightly
The price is $610
Oct 14 - Oct 15
Total with taxes and fees
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.
$304 nightly
The price is $309
Oct 20 - Oct 21
Total with taxes and fees
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.
$686 nightly
The price is $699
Oct 14 - Oct 15
Total with taxes and fees
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.
$457 nightly
The price is $466
Oct 14 - Oct 15
Total with taxes and fees
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.
$372 nightly
The price is $382
Oct 18 - Oct 19
Total with taxes and fees
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.
$431 nightly
The price is $439
Nov 10 - Nov 11
Total with taxes and fees
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 front desk hospitality was very great and the room was very clean and the accommodation perfect, the breakfast was excellent and free parking. I will go again very near future ."
Eyob 2-night trip
Posted less than an hour ago
Home2 Suites by Hilton Lewes Rehoboth Beach

Find out more about Greenwood

Everything you need to know about Greenwood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Greenwood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Greenwood vacation 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 low season months. For more hustle and bustle, you may prefer to visit Greenwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $216 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Greenwood rentals

At Expedia, we put the best Greenwood vacation 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 vacation.

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.

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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?

Bay Front Water & Beach Front Broadkill Pet Friendly Sleeps 12 4Bed 4Bath 4Floor: 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 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection 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 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.