Holiday Homes in Greenwood

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Featured Holiday Homes in Greenwood and around

Our top choices for Greenwood holiday homes

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

Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

9.8 out of 10, Exceptional, (22)
"It was a awesome great comfy house."
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

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.

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 €204
includes taxes & fees
26 Aug - 27 Aug
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

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

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

10.0 out of 10, Exceptional, (24)
"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!

Cozy cottage on the Miller farm.

10.0 out of 10, Exceptional, (229)
"Awesome place. "
Cozy cottage on the Miller farm.

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

Mill Pond Acres home w/pool table, Xbox X, free WIFI

2.0 star property
8.4 out of 10, Very good, (8)
"Nice house simply needs a few upgrades like furniture in the living room and WiFi bandwidth needs improved. I would rent this place again regardless."
Mill Pond Acres home w/pool table, Xbox X, free WIFI

Luxury Treehouse with Large Deck

10.0 out of 10, Exceptional, (8)
"This is a place that I we can’t wait to go back to!! Everything was so unique and done up with thought. You have to go and read the beautiful story behind the “Tree House” "
Luxury Treehouse with Large Deck

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 €602
includes taxes & fees
4 Sept - 5 Sept
Cozy home w/ amazing sunsets minutes to DE/MD Beaches: Come enjoy! 4 BR 3 BATH

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

10.0 out of 10, Exceptional, (93)
"Perfect place to hang your hat after exploring Lewes DE"
Clean & cozy townhome. Easy access to trails & historic Lewes. 5 mins to beach.

The Plantations condo with sunroom - near beach

7.8 out of 10, Good, (10)
"Nice, comfortable stay."
The Plantations condo with sunroom - near beach

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

♦︎ 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 ♦︎

1 Mississippi Ave. Bayfront Broadkill Beach

8.0 out of 10, Very good, (1)
"There was a bit if confusion out the gate as a Real Estate company handles the booking, not VRBO but once that was figured out it was smooth. Good: Amazing views. Spent much of the stay staring out the windows. Kitchen was well equipped. House is clean and well maintained. Easy beach access. Bay is relatively warm and very calm.Things to note: If you have older adults with you or toddlers, theres a ton of steps. The second king bed is in what is essentially a finished garage on the ground floor....
1 Mississippi Ave. Bayfront Broadkill Beach
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