Greenwood Vacation Rentals

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Vacation Rentals in Greenwood

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

✨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!

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 ¥13,254
¥29,167 total
includes taxes & fees
Sep 1 - Sep 2
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

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

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

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 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 ¥58,518
¥82,030 total
includes taxes & fees
Sep 29 - Sep 30
Cozy home w/ amazing sunsets minutes to DE/MD Beaches: Come enjoy! 4 BR 3 BATH

Cozy home minutes from Lewes and Rehoboth Beach

10.0 out of 10, Exceptional, (33)
"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, (201)
"A nice peaceful, beautiful getaway that is still close to Rehoboth!"
Cozy Waterfront Cottage– Dog Friendly & Fully Stocked!

ON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.

10.0 out of 10, Exceptional, (100)
"The property was beautiful. Clean house with everything you would need on a private, quiet beach. I would definitely return. "
ON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.

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

10.0 out of 10, Exceptional, (1)
"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

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.

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.

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!

♦︎ Waterfront ♦︎ Pet Friendly ♦︎ Broadkill Beach ♦︎

9.8 out of 10, Exceptional, (188)
"We really enjoyed our stay at Snow Goose! The place was quiet and peaceful, we loved the location right on the beach, and we absolutely loved watching the sunrises in the morning! We would definitely stay here again!"
♦︎ Waterfront ♦︎ Pet Friendly ♦︎ Broadkill Beach ♦︎

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.

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

10.0 out of 10, Exceptional, (25)
"Nice stay… good family home…. Lots of sleeping accommodations…. A few steps from the beach!!!!! Great host!!!!!"
NEW! Bowers Retreat - Sleeps 10 - Steps to beach! 10 Minutes to DE Turf!

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

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

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

9.4 out of 10, Exceptional, (3)
"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!
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

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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?

Captain's Quarters: Visitors like this Greenwood vacation home rental. It is located near the beach and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 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.