Greenwood Holiday Rentals

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Holiday Rentals in Greenwood

Our top choices for Greenwood holiday rentals

Captain's Quarters

9.8 out of 10, Exceptional, (97)
"This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. "
Captain's Quarters

Bayfront Cottage with Spectacular Views

10.0 out of 10, Exceptional, (457)
"Well stocked house with everything you need for an amazing vacation."
Bayfront Cottage with Spectacular Views

Cozy Waterfront Cottage– Dog Friendly & Fully Stocked!

10.0 out of 10, Exceptional, (202)
"A nice peaceful, beautiful getaway that is still close to Rehoboth!"
Cozy Waterfront Cottage– Dog Friendly & Fully Stocked!

GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE

10.0 out of 10, Exceptional, (125)
"Our 3rd time staying at the cottage & it was wonderful. Can’t wait to come back :)"
GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE

✨Pet Friendly✨Walk to the beach from this coastal cottage on Broadkill!

10.0 out of 10, Exceptional, (102)
"We had a wonderful weekend getaway. The location was incredibly quiet—perfect for relaxing and disconnecting. The house was clean, well-equipped, and beautifully maintained. Ideal spot for anyone looking to unwind, with the beach just a short walk away. Will definitely stay again!"
✨Pet Friendly✨Walk to the beach from this coastal cottage on Broadkill!

Prime Hook Retreat - Amazing View of the Refuge - Beach Access Across the Street

10.0 out of 10, Exceptional, (37)
"Clean, quiet and great location "
Prime Hook Retreat - Amazing View of the Refuge - Beach Access Across the Street

Cozy home minutes from Lewes and Rehoboth Beach

10.0 out of 10, Exceptional, (34)
"Had a good stay. Was very clean."
Cozy home minutes from Lewes and Rehoboth Beach

Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!

2.0 star property
10.0 out of 10, Exceptional, (11)
Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!

Clean & cozy townhome. Easy access to trails & historic Lewes. 5 mins to beach.

10.0 out of 10, Exceptional, (94)
"We enjoyed our time in celebration of a wedding. Our host was very communicative, helpful and even did a dance to help improve the weather! Also appreciated that they are dog friendly."
Clean & cozy townhome. Easy access to trails & historic Lewes. 5 mins to beach.

Escape to this charming beach cottage along the coast of Broadkill Beach

10.0 out of 10, Exceptional, (2)
"Clean, cozy and very detailed oriented. It is a great choice for a beach stay."
Escape to this charming beach cottage along the coast of Broadkill Beach

Cozy home w/ amazing sunsets minutes to DE/MD Beaches: Come enjoy! 4 BR 3 BATH

9.4 out of 10, Exceptional, (15)
"Exactly as described and nicer than the pictures, and the pictures were amazing. "
The price is AU$860
includes taxes & fees
29 Sept - 30 Sept
Cozy home w/ amazing sunsets minutes to DE/MD Beaches: Come enjoy! 4 BR 3 BATH

Waterfront- Yr 2025 Downstair den; no pet fees; toiletries for your convenience.

9.8 out of 10, Exceptional, (47)
"The stay was very enjoyable. Being on a semi private beach area was very relaxing."
Waterfront- Yr 2025 Downstair den; no pet fees; toiletries for your convenience.

3+ Night Rentals Allowed - Large Pet Friendly Home with Fenced-In Back Yard

9.0 out of 10, Wonderful, (22)
"Great place for family and dogs!"
3+ Night Rentals Allowed - Large Pet Friendly Home with Fenced-In Back Yard

Cozy Beach Front Cottage Pet Friendly

10.0 out of 10, Exceptional, (27)
"Great stay for a couple. Cozy home, quiet neighborhood, kitchen had all we needed as we brought food to heat and eat. We went birding at a bunch of parks. The beach was pretty private only a handful of people walking, no loud kids, really relaxing. "
Cozy Beach Front Cottage Pet Friendly

Beachfront Sunrise - Waterfront house w/ bay and refuge views Sleeps 6-8 people

10.0 out of 10, Exceptional, (174)
"What a lovely house with beautiful panoramic windows and views of the bay and beach! The house was well-maintained and well-equipped for guests, with plenty of space for this family of four dog. (We loved the doggie designated towels.) The hosts were responsive and accommodating; their TLC for the house is apparent and appreciated. If given the opportunity, we will definitely come back. "
Beachfront Sunrise - Waterfront house w/ bay and refuge views Sleeps 6-8 people

Great Escape ~Unique Beach Views ~ Right on the Water~Child Items ~ Linens

10.0 out of 10, Exceptional, (116)
"This home is beautiful. Incredible views from all levels. It was clean and well stocked with everything you could need to feel at home. Plenty of beach toys and chairs for everyone. The kitchen was a delight with all a chef could desire. The owners Tess & Andy were wonderful and highly communicative. Lots of TLC put into this home. We would highly recommend. "
Great Escape ~Unique Beach Views ~ Right on the Water~Child Items ~ Linens

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

9.8 out of 10, Exceptional, (45)
"This is the best place I have stayed at. The hosts were wonderful. Their hospitality is unmatched. They have a beautiful property that is well maintained and close to all Delaware has to offer that we were looking for. The place was clean and in such a safe part of town. We will definitely be staying here again! "
The price is AU$307
includes taxes & fees
1 Sept - 2 Sept
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

Pet Friendly Broadkill Beach retreat—where coastal living, natural beauty, and relaxation come together in perfect harmony!

10.0 out of 10, Exceptional, (1)
"lovely property. the door lock was tight, but we managed fine.i was concerned with the outside, adorable cat that seems to sleep on the porches. i really hope he has a home somewhere"
Pet Friendly Broadkill Beach retreat—where coastal living, natural beauty, and relaxation come together in perfect harmony!

Village of Five Points condo with pool, gym, and tennis access

8.0 out of 10, Very good, (5)
"Property is well kept, clean and has everything needed for relaxing getaway. It's located conveniently from shopping, restaurants, downtown and Beech."
Village of Five Points condo with pool, gym, and tennis access

3 bedroom Family Friendly condo - Last Minute Labor Day Opening

9.8 out of 10, Exceptional, (160)
"We had a wonderful time at this cute property! "
3 bedroom Family Friendly condo - Last Minute Labor Day Opening
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

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$307 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?

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 Delaware Technical Community College Georgetown Campus 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.