Greenwood Holiday Rentals from €182: Search Short-Term Rentals

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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

Lincoln

andy O.

includes taxes & fees

8 Oct - 9 Oct

A modern living space with a dining area, sofa, and kitchen.

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

Milford

Jill M.

A bedroom with a bed, a dresser, a mirror, and a door leading to another room.

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

Milford

Shaine L.

includes taxes & fees

19 Oct - 20 Oct

A patio area with outdoor seating, string lights, and potted plants.

4. Poe Themed Home Close to Beaches and DE Turf

Milford

Dee Z. B.

includes taxes & fees

8 Oct - 9 Oct

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!

Frederica

nahum f.

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!

Georgetown

Haileigh

includes taxes & fees

8 Oct - 9 Oct

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

Lincoln

Jessica W.

includes taxes & fees

19 Oct - 20 Oct

8. Waterfront studio w/ pool - shopping and beaches

Lincoln

Paula R.

includes taxes & fees

19 Oct - 20 Oct

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

Lincoln

Beth S.

includes taxes & fees

8 Oct - 9 Oct

10. The Little house W/ Pool & Spa

Lincoln

veronica d.

includes taxes & fees

14 Oct - 15 Oct

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

Georgetown

ANA

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.

12. Turnbridge Manor

Denton

Glenn S.

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!

Milford

Krista L.

includes taxes & fees

8 Oct - 9 Oct

A room with a large window overlooking a river, a wicker chair, and a glass table.

14. Spacious Condo•Pond Views•Centrally located

Plantations East

Jennifer B.

includes taxes & fees

25 Oct - 26 Oct

A swimming pool with a tiled edge, surrounded by potted plants and outdoor furniture.

15. Mini Aruba RV/Glamping Tent

Dover

Robert N.

includes taxes & fees

19 Oct - 20 Oct

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!

Villages of Five Points

Mandy M.

includes taxes & fees

4 Nov - 5 Nov

A kitchen with white cabinets, a granite countertop, a stainless steel refrigerator, a microwave, and a stove.

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

Milton

Lauren B.

includes taxes & fees

3 Nov - 4 Nov

A round window with a view of a garden, a tree, and a building in the background.

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

Kitts Hummock

"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...

Alex L.

includes taxes & fees

19 Oct - 20 Oct

A spacious living area with a large sofa, a dining table, and a kitchen with white cabinets and a wooden countertop.

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

Milton

Alexis P.

includes taxes & fees

8 Oct - 9 Oct

A modern kitchen with a large island, bar stools, and pendant lighting.

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

Magnolia

John K.

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Top Greenwood Hotel Reviews

Hyatt House Lewes/Rehoboth Beach

10/10 Excellent

"Great stay, clean rooms, good breakfast, big pool, great staff. Didn’t get to bring our pet but the hotel is very pet friendly. Will be back!"

Quality Inn & Suites Harrington - Milford

8/10 Good

"The staff was lovely and their complimentary breakfast was better than what I expected. They had a waffle machine and many other options. The room was a bit outdated and I didn’t expect much but it produced the atmosphere of a motel. Overall it was decent given the location and price."

Luxury Treehouse with Large Deck

10/10 Excellent

"What a joy it was to be able to stay at this property. My husband and I traveled to Delaware for a wedding and the property was perfect for the two of us. The owner is super helpful and very attentive. We both felt right at home in this space and lived the porch area.. thanks for making and sharing such an awesome place with travelers."

Best Western Plus Easton Inn & Suites

8/10 Good

"Very good location, there was variety at breakfast and the food and coffee very good. The room was in very good condition; there was not enough lighting in the room or bathroom. The toilet paper and tissues were very cheap. Overall our experience was very good and we enjoyed our stay."

Holiday Inn Express Hotel & Suites Harrington-Dover area, DE by IHG

8/10 Good

"Room was mostly clean but definitely had a pet odor in it. We had to burn candles to lessen the odor when we were in the room. Had an issue when we had to extend our trip a day because we had used Expedia. We were able to get another reservation and spoke directly to the front desk about staying in the same room and not being disturbed. (This was a working trip and we had been up almost 26 hours which is why we wanted everything set when we got to the hotel to sleep) We were guaranteed everything was set. The next morning housekeeping knocked on our door (waking us up) and then about 30 minutes later the front desk called, waking us up a second time. They apologized, but that isn’t much of a consolation when all you needed was sleep. Parking was great, and staff were nice. The breakfast was also good."

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, apart-hotels, 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 €182 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?

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.

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Check prices for these dates

Our top choices for Greenwood holiday rentals

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

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

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

4. Poe Themed Home Close to Beaches and DE Turf

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

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

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