Greenwood Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Greenwood

3 bedroom Family Friendly condo - Last Minute August Openings

9.8 out of 10, Exceptional, (157)
"Beaches, shopping, lots to do, and a welcoming host!"
3 bedroom Family Friendly condo - Last Minute August Openings

Stunning, light-filled beachfront sanctuary with full views of Delaware Bay.

9.6 out of 10, Exceptional, (28)
"Beautiful home for a weekend away with friends. Loved the views from the rooftop deck. Would definitely stay here again!"
Stunning, light-filled beachfront sanctuary with full views of Delaware Bay.

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

10.0 out of 10, Exceptional, (100)
"Our stay at the cottage was fantastic! The location was beautiful and quiet and just a quick walk to the beach. The house was very clean upon our arrival. The host was a great communicator and answered messages quickly. We loved that we could bring our dog. We would definitely consider staying here again!"
✨Pet Friendly✨Walk to the beach from this coastal cottage on Broadkill!

Cozy Beach Front Cottage Pet Friendly w/no pet fees

10.0 out of 10, Exceptional, (25)
"This cottage was perfect for my family of 5 plus dog. The neighborhood is quiet and we enjoyed the long weekend escape! "
Cozy Beach Front Cottage Pet Friendly w/no pet fees

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

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

Captain's Quarters

9.8 out of 10, Exceptional, (97)
"We had a great weekend stay for a tournament. Thank you!"
Captain's Quarters

17059 S Brandt Street Unit 3201

17059 S Brandt Street Unit 3201

Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

9.4 out of 10, Exceptional, (3)
"Adorable cottage. Excellent location. We will definitely rent again. "
Charming bungalow w water views in Bowers Beach AC WiFi Dover Downs AFB DE Turf

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

10.0 out of 10, Exceptional, (172)
"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

101 Lakeside Drive - Newly listed Plantations West Townhouse

8.4 out of 10, Very good, (9)
"Renting was easy and the check in was very quick. Nice quiet property close to everything you’d want to do!"
101 Lakeside Drive - Newly listed Plantations West Townhouse

Newly renovated brand new listing - Just Steps from the Beach in Broadkill!

9.0 out of 10, Wonderful, (2)
"Perfect getaway! House is gorgeously furnished and has everything you need to stay & relax. Our family had a great time! House is very clean and modern. We felt very comfortable here. Host was responsive, respectful and very easy to communicate with. We had a wonderful time and will definitely stay here again. "
Newly renovated brand new listing - Just Steps from the Beach in Broadkill!

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

GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE

10.0 out of 10, Exceptional, (123)
"Our 3rd time staying at the cottage & it was wonderful. Can’t wait to come back :)"
GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE

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

9.6 out of 10, Exceptional, (14)
"Exactly as described and nicer than the pictures, and the pictures were amazing. "
The price is AU$1,043
includes taxes & fees
2 Sept - 3 Sept
Cozy home w/ amazing sunsets minutes to DE/MD Beaches: Come enjoy! 4 BR 3 BATH

Tranquil Beach Cottage directly across from beach access-Pets & Children Welcome

9.6 out of 10, Exceptional, (118)
"Once again a great stay in this house in it's central location. It's had a few upgrades since we last stayed which has made the kitchen even better."
Tranquil Beach Cottage directly across from beach access-Pets & Children Welcome

Cozy home minutes from Lewes and Rehoboth Beach

10.0 out of 10, Exceptional, (31)
"Had a good stay. Was very clean."
Cozy home minutes from Lewes and Rehoboth Beach

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

Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!

2.0 star property
10.0 out of 10, Exceptional, (8)
Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!

Charming 3-bedroom, 2 bath-room house with WiFi and AC in Lewes.

Charming 3-bedroom, 2 bath-room house with WiFi and AC in Lewes.

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

9.8 out of 10, Exceptional, (43)
"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$365
includes taxes & fees
26 Aug - 27 Aug
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Greenwood Hotel Reviews

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?

Stunning, light-filled beachfront sanctuary with full views of Delaware Bay.: This holiday home rental outside of Greenwood is located on the beach, and has a balcony, a rooftop terrace and a BBQ to put you at ease in your new surroundings. It has 3 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 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.