Greenwood Vacation Rentals from ￥29,059: Search Short-Term Rentals

Q: What are some of the best vacation rentals that Greenwood has to offer?

Bayfront Cottage with Spectacular Views : Visitors like this Greenwood vacation home rental. It is located on the beach and has a fireplace, a patio, 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. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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Vacation Rentals in Greenwood

"The house was so cute! The gardens in the back and around the front entry were really amazing and added to the charm. When you walk in the little hall way goes left to a living area or right to a set of stairs that leads to the upper floor. The upstairs has a huge bathroom and 3 bedrooms. The bedroom all the way to the left has 2 beds and a kitchenette in it which was pretty cool. The other side of the hall has a queen bedroom and a single bedroom. The upstairs also has a door at the bottom...

"Amazing stay! The home was beautiful, cozy, and extremely well stocked. Beautiful and peaceful location. We felt very much at home. We would love to come back for another visit!"

"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!"

"Was great for are trip host was great when needed help "

"Having rented homes on the water for over 30 years we found "Great Escape" to be rated in the top tier. Starting with Tess the owner's communication and endless information to be accurate and valuable. The house was immaculate with everything needed for an enjoyable week. Looking forward to renting again .... john h "

"Our 3rd time staying at the cottage & it was wonderful. Can’t wait to come back :)"

"This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. "

"We had an amazing experience at this cottage! It was very home like an private. I hope to visit again one day!"

"This home is beautiful and clean and perfectly located for us to take advantage of the beaches as well as the baseball tournament that our grandson was in. The Host was very responsive and we thoroughly enjoyed our stay here."

￥85,944 total

includes taxes & fees

Sep 29 - Sep 30

"A great place to stay to see the horseshoe crabs at Full moon! Nicely equipped house on the perfect quiet beach. Close enough to restaurants and stores to be easy…"

"Our stay was lovely! The house was clean, spacious for our family (5 adults, 2 kids), the beds were clean and it was in a quiet neighborhood. We would stay here again! "

"Beautiful home great stay will do again "

"Perfect cottage! Clean, nicely stocked with essentials, and right on the beach. The dogs appreciated the fenced yard. Flies were biting so be sure to take bug spray. Thank you for allowing us to stay at your home!"

"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! "

￥29,059 total

includes taxes & fees

Oct 4 - Oct 5

"Wonderful place for nature, peace, and quiet. Beautiful sunrises every morning. A great getaway."

￥108,406 total

includes taxes & fees

Oct 1 - Oct 2

Beach nearby, sun loungers, beach towels

3 bedrooms, travel crib, free WiFi, bed sheets

"A nice peaceful, beautiful getaway that is still close to Rehoboth!"

"We really enjoyed our stay!"

"Loved our stay at this cozy cottage at Prime Hook Beach. We were able to enjoy the space on the rainy days, hang out on the beach on the nice days and find tons of shells or hop to neighboring beaches and towns. Great spot and great property. The listing is accurate. "

"Karen and Kaylyn were wonderful hosts!! The rental was perfect for our family, plenty of space to spread out!! The rental was very clean, stocked and at a perfect location! Will definitely rent from them again!!"

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Top Greenwood Hotel Reviews

Springhill Suites By Marriott Frederica

10/10 Excellent

"A fantastic stay with a swift check-in and a very quiet, comfortable room. The hotel is modern (2-3 years old) and well-maintained. We loved the spacious bathroom with a separate toilet, a separate shower, and two sinks. The free breakfast had a wonderful array of oatmeal toppings. The fire pit was a lovely amenity. When our shower door wouldn't open, the staff sent a repairperson who fixed it immediately."

Home2 Suites by Hilton Lewes Rehoboth Beach

10/10 Excellent

"Was pleasantly surprised with a very modern Hotel. The room was incredibly spacious and clean and comfortable! Loved my stay. Free breakfast in the morning was presented well, good coffee and so many options in a very well thought out space that could accommodate a lot of people.. did not feel crowded what so ever. Very nice. I can see why people would want long term stays here!"

Find out more about Greenwood

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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?

Bayfront Cottage with Spectacular Views: Visitors like this Greenwood vacation home rental. It is located on the beach and has a fireplace, a patio, 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. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.

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Greenwood Vacation Rentals

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Vacation Rentals in Greenwood

Historic home, great yard & Walk to Dogfish Head Brewery!

Bayfront Cottage with Spectacular Views

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

12 Mi to Dtwn Lewes & Beach: Delaware Home w/ Deck

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

GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE

Captain's Quarters

Cozy Beach Front Cottage Pet Friendly

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

Nirvana on the beach

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

Piper's Paradise - Beachfront, Views, Sonos, Sauna, Tesla charger, Arcade

🔷 Water Front 🔷 Pet Friendly 🔷 Prime Hook Beach 🔷

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

Delaware Beachfront Private Getaway on the Bay

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

Cozy Waterfront Cottage– Dog Friendly & Fully Stocked!

3 bedroom Family Friendly condo - September and October Specials

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

Beach House at Broadkill- Sleeps 13, Dog Friendly

Top Greenwood Hotel Reviews

Springhill Suites By Marriott Frederica

Home2 Suites by Hilton Lewes Rehoboth Beach

Hampton Inn Milford

Motel 6 Seaford, DE

Microtel Inn & Suites by Wyndham Dover

Hyatt House Lewes/Rehoboth Beach

Comfort Inn & Suites Milford

Best Western Plus Easton Inn & Suites

Quality Inn

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