Greenwood Vacation 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

Vacation Rentals in Greenwood

Captain's Quarters

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

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

10.0 out of 10, Exceptional, (100)
"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!

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.

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 CA $162
CA $318 total
includes taxes & fees
Aug 18 - Aug 19
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

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

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

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

9.4 out of 10, Exceptional, (15)
"Exactly as described and nicer than the pictures, and the pictures were amazing. "
The price is CA $674
CA $934 total
includes taxes & fees
Sep 2 - Sep 3
Cozy home w/ amazing sunsets minutes to DE/MD Beaches: Come enjoy! 4 BR 3 BATH

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 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

Cozy Waterfront Cottage– Dog Friendly & Fully Stocked!

10.0 out of 10, Exceptional, (200)
"A nice peaceful, beautiful getaway that is still close to Rehoboth!"
Cozy Waterfront Cottage– Dog Friendly & Fully Stocked!

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!

NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

10.0 out of 10, Exceptional, (23)
"The house was amazing, and close to Killens Pond State Park where we had additional family camping."
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

Villages of Five Points 2nd floor condo - great location & amenities!

9.6 out of 10, Exceptional, (7)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Very nice place! Had everything we needed. Loved the pool!"
Villages of Five Points 2nd floor condo - great location & amenities!

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

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.

Cozy Beach Front Cottage Pet Friendly w/no pet fees

10.0 out of 10, Exceptional, (26)
"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

Mini Aruba Glamper in Dover with WiFi, AC and guest access to backyard oasis

10.0 out of 10, Exceptional, (2)
"My husband and I stayed for two nights. The oasis makes you feel like you’re vacationing in the Caribbean. The camper is clean and comfortable for two people. Everything was perfect and cannot wait to return!"
The price is CA $224
CA $353 total
includes taxes & fees
Sep 16 - Sep 17
Mini Aruba Glamper in Dover with WiFi, AC and guest access to backyard oasis

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

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
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 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?

Stunning, light-filled beachfront sanctuary with full views of Delaware Bay.: Visitors like this Greenwood vacation home rental. It is located on the beach and has a balcony, a rooftop terrace, and a barbecue grill 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 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 Delaware Technical Community College Georgetown Campus 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.