Greenwood Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Greenwood

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

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

Greenwood
9.8 out of 10, Exceptional, (31)
"Great place to stay with a family. Very nicely decorated and clean. "
United States
Meg E.
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf
Interior
Charming 3-bedroom Ranch in delightful Dover with AC

Charming 3-bedroom Ranch in delightful Dover with AC

Dover
10.0 out of 10, Exceptional, (1)
"Host was great"
United States
mark o.
Charming 3-bedroom Ranch in delightful Dover with AC
Outdoor pool
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

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

Georgetown
9.8 out of 10, Exceptional, (47)
"Very thoughtful and hospitable hosts. We had a lovely time!"
United States
Eve S.
The price is HK$701
HK$1,526 total
includes taxes & fees
5 Dec - 6 Dec
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
Fridge, microwave, oven, stovetop
Captain's Quarters

Captain's Quarters

Frederica
9.8 out of 10, Exceptional, (104)
"This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. "
United States
Criselle A.
Captain's Quarters
Terrace/patio
Bayfront Cottage with Spectacular Views

Bayfront Cottage with Spectacular Views

Slaughter Beach
10.0 out of 10, Exceptional, (472)
"We enjoyed our stay very much. Would definitely consider going back. The views from the deck were beautiful. Short walk to the beach. Quiet & relaxing stay. "
United States
Bonnie D.
Bayfront Cottage with Spectacular Views
On the beach, sun-loungers
Delaware Beachfront Private Getaway on the Bay

Delaware Beachfront Private Getaway on the Bay

Milford
9.8 out of 10, Exceptional, (193)
"We've stayed here a couple of other times- house is perfect, location is wonderful! It was nice and quiet this time of year which is exactly what we were looking for. Our pup had a blast...the fenced in yard is perfect! "
United States
Dana M.
The price is HK$1,425
HK$4,130 total
includes taxes & fees
5 Dec - 6 Dec
Delaware Beachfront Private Getaway on the Bay
Beach nearby
Beach House at Broadkill- Sleeps 13, Dog Friendly

Beach House at Broadkill- Sleeps 13, Dog Friendly

Milton
9.4 out of 10, Exceptional, (6)
"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!!"
United States
Angie B.
Beach House at Broadkill- Sleeps 13, Dog Friendly
Smart TV
Pets Friendly, Waterfront, Large backyard, Bonfire with grill, outside shower

Pets Friendly, Waterfront, Large backyard, Bonfire with grill, outside shower

Milton
10.0 out of 10, Exceptional, (12)
"The host was very friendly and responsive. We love taking our puppy to her first trip to the beach!"
United States
Mary-Liz E.
The price is HK$1,168
HK$2,692 total
includes taxes & fees
3 Dec - 4 Dec
Pets Friendly, Waterfront, Large backyard, Bonfire with grill, outside shower
Fridge, microwave, oven, stovetop
3+ Night Rentals Allowed - Large Pet Friendly Home with Fenced-In Back Yard

3+ Night Rentals Allowed - Large Pet Friendly Home with Fenced-In Back Yard

Milton
8.8 out of 10, Excellent, (28)
"Beautiful house with lots of space and activities for the family. We had a great time and took advantage of the privileged location to explore the beach and bike around the town."
United States
Carlos M.
3+ Night Rentals Allowed - Large Pet Friendly Home with Fenced-In Back Yard
Exterior
Cool Little Cottage Minutes forFrom Beaches, Shopping and Dining

Cool Little Cottage Minutes forFrom Beaches, Shopping and Dining

Lewes
10.0 out of 10, Exceptional, (142)
"We loved our stay! We will definitely be back! The host was so nice and friendly!! Just a charming place. "
United States
Heidi G.
Cool Little Cottage Minutes forFrom Beaches, Shopping and Dining
Exterior detail
Historic home, great yard & Walk to Dogfish Head Brewery!

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

Milton
9.8 out of 10, Exceptional, (7)
"We had a great experience! It was clean, cozy, and had easy access to a number of locations. Will book again!"
United States
Jeffrey
The price is HK$470
HK$919 total
includes taxes & fees
3 Dec - 4 Dec
Historic home, great yard & Walk to Dogfish Head Brewery!
3 bedrooms, iron/ironing board, WiFi, bed sheets
Delaware Turf Bungalow’s Sister!

Delaware Turf Bungalow’s Sister!

Milford
10.0 out of 10, Exceptional, (2)
"This bungalow was the perfect getaway for the weekend. It was clean, cozy and had enough space for my children and I to relax without being on top of each other. We were close enough to several beaches and the boardwalk but far enough away to get away from the hustle and bustle of the big beach town. The host was amazing. She was so nice to communicate with and very accommodating. She made us feel very welcomed and even suggested some sights to check out around the area. The whole experience was...
United States
Christina T.
Delaware Turf Bungalow’s Sister!
Smart TV, fireplace
Secluded Beach home with amazing views.

Secluded Beach home with amazing views.

Milford
10.0 out of 10, Exceptional, (44)
"Easy check in, amazing views, clean, just as described! "
United States
Marissa S.
Secluded Beach home with amazing views.
Fridge, microwave, oven, stovetop
Charming 2-bedroom bungalow with WiFi, AC in delightful Milton

Charming 2-bedroom bungalow with WiFi, AC in delightful Milton

Milton
10.0 out of 10, Exceptional, (5)
"Great place to stay! Very comfortable and conveniently located to Rehoboth."
United States
Jasmine P.
Charming 2-bedroom bungalow with WiFi, AC in delightful Milton
Interior
12 Mi to Dtwn Lewes & Beach: Delaware Home w/ Deck

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

3.0 star property
Georgetown
10.0 out of 10, Exceptional, (1)
"Was great for are trip host was great when needed help "
United States
Alex
12 Mi to Dtwn Lewes & Beach: Delaware Home w/ Deck
Exterior
Cozy cottage on the Miller farm.

Cozy cottage on the Miller farm.

Milford
10.0 out of 10, Exceptional, (240)
"We’ve stayed here several timesWe always feel welcome and the cottage is perfect!!"
United States
Ron F.
Cozy cottage on the Miller farm.
Property grounds
GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE

GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE

Milford
10.0 out of 10, Exceptional, (133)
"Stay was great! House was clean and area was quaint and quiet. "
United States
Allison G.
GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE
Terrace/patio
Coastal Club Community Resort Style Amenities - 6 BR's 4 Baths in Lewes-Rehoboth

Coastal Club Community Resort Style Amenities - 6 BR's 4 Baths in Lewes-Rehoboth

Lewes
10.0 out of 10, Exceptional, (10)
"The house was great. Loved the pool table and the yard. Lots of space, very clean and lots of room for everyone."
United States
Matt H.
Coastal Club Community Resort Style Amenities - 6 BR's 4 Baths in Lewes-Rehoboth
Interior
EXCLUSIVELY YOURS! Private Beach Path, Double Water Access, and Dog Friendly.

EXCLUSIVELY YOURS! Private Beach Path, Double Water Access, and Dog Friendly.

Milton
10.0 out of 10, Exceptional, (83)
"Beautiful area. If you are looking for a quiet vacation away from the main beach areas, I highly recommend. Wendy was fabulous!!"
United States
Heather C.
EXCLUSIVELY YOURS! Private Beach Path, Double Water Access, and Dog Friendly.
Exterior detail
✨Pet Friendly✨Walk to the beach from this coastal cottage on Broadkill!

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

Milton
10.0 out of 10, Exceptional, (108)
"Our stay was a great experience. The house was clean and nicely decorated. Gina was very easy to contact and the check-in process was very easy. The location is convenient and it’s only steps from the beach. The outdoor shower and hose were also great features! We would definitely recommend to anyone looking for a peaceful and relaxing beach vacation! "
United States
Lisa H.
✨Pet Friendly✨Walk to the beach from this coastal cottage on 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

Home2 Suites by Hilton Lewes Rehoboth Beach

Home2 Suites by Hilton Lewes Rehoboth Beach

10/10 Excellent
"Always a fantastic stay!"
Brandon 1-night trip
Posted 3 days ago
Home2 Suites by Hilton Lewes Rehoboth Beach

Find out more about Greenwood

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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?

Captain's Quarters: This holiday home rental outside of Greenwood is located near the beach, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 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.