Greenwood Holiday Rentals

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Holiday Rentals in Greenwood

Historic home, great yard & Walk to Dogfish Head Brewery!
10.0 out of 10, Exceptional, (3)
"Enjoyed the house very clean liked the area. "
The price is NZ$359
includes taxes & fees
14 Oct - 15 Oct
Historic home, great yard & Walk to Dogfish Head Brewery!
Cozy Beach Front Cottage Pet Friendly
10.0 out of 10, Exceptional, (27)
"We had an amazing experience at this cottage! It was very home like an private. I hope to visit again one day!"
Cozy Beach Front Cottage Pet Friendly
Bayfront Cottage with Spectacular Views
10.0 out of 10, Exceptional, (462)
"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!"
Bayfront Cottage with Spectacular Views
✨Pet Friendly✨Walk to the beach from this coastal cottage on Broadkill!
10.0 out of 10, Exceptional, (104)
"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!
12 Mi to Dtwn Lewes & Beach: Delaware Home w/ Deck
3.0 star property
10.0 out of 10, Exceptional, (1)
"Was great for are trip host was great when needed help "
12 Mi to Dtwn Lewes & Beach: Delaware Home w/ Deck
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!
9.8 out of 10, Exceptional, (46)
"Great location, peaceful, clean, quaint & accommodating hosts"
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, (130)
"Nice quiet spot, steps away from the Bay! Very beautiful!"
GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE
Piper's Paradise - Beachfront, Views, Sonos, Sauna, Tesla charger, Arcade
10.0 out of 10, Exceptional, (44)
"Beautiful home great stay will do again "
Piper's Paradise - Beachfront, Views, Sonos, Sauna, Tesla charger, Arcade
Newly renovated brand new listing - Just Steps from the Beach in Broadkill!
9.6 out of 10, Exceptional, (5)
Newly renovated brand new listing - Just Steps from the Beach in Broadkill!
Cool Little Cottage Minutes forFrom Beaches, Shopping and Dining
10.0 out of 10, Exceptional, (141)
"The cottage is a cute love nest a short drive away from Lewes and other area attractions. We had a pleasant stay!"
Cool Little Cottage Minutes forFrom Beaches, Shopping and Dining
Delaware Beachfront Private Getaway on the Bay
9.8 out of 10, Exceptional, (191)
"Wonderful place for nature, peace, and quiet. Beautiful sunrises every morning. A great getaway."
The price is NZ$1,051
includes taxes & fees
14 Oct - 15 Oct
Delaware Beachfront Private Getaway on the Bay
Beach House at Broadkill- Sleeps 13, Dog Friendly
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!!"
Beach House at Broadkill- Sleeps 13, Dog Friendly
ON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.
10.0 out of 10, Exceptional, (103)
"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.
♦︎ Waterfront ♦︎ Pet Friendly ♦︎ Broadkill Beach ♦︎
9.8 out of 10, Exceptional, (194)
"What a beautiful beach house! Exactly what I was looking for when booking. Quiet, private beach escape."
♦︎ Waterfront ♦︎ Pet Friendly ♦︎ Broadkill Beach ♦︎
3+ Night Rentals Allowed - Large Pet Friendly Home with Fenced-In Back Yard
8.8 out of 10, Excellent, (26)
"Property was spacious, clean, and secure. Neighborhood was private and friendly. The short walk to the beach was nice. It was great that we were able to bring our large dog. Overall a pleasant experience. "
3+ Night Rentals Allowed - Large Pet Friendly Home with Fenced-In Back Yard
3 bedroom Family Friendly condo - September and October Specials
9.8 out of 10, Exceptional, (164)
"We really enjoyed our stay!"
3 bedroom Family Friendly condo - September and October Specials
Cozy home minutes from Lewes and Rehoboth Beach
10.0 out of 10, Exceptional, (34)
"Second stay at this house and like last time, it was a great experience. Great location and AC is very welcome after hot days. "
Cozy home minutes from Lewes and Rehoboth Beach
Captain's Quarters
9.8 out of 10, Exceptional, (100)
"This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. "
Captain's Quarters
Beachfront Sunrise - Waterfront house w/ bay and refuge views Sleeps 6-8 people
10.0 out of 10, Exceptional, (178)
"Our 5 members truly enjoyed the privacy of the beach and the large picture windows to gaze on the beach when it was too hot to be in the sun. The lower level was perfect for one of our members and for coming in and out from the beach. We appreciated two showers and toilets. The horseshoe crabs were a bit much at first, but we just got accustomed to them. We had a very relaxing, enjoyable week."
Beachfront Sunrise - Waterfront house w/ bay and refuge views Sleeps 6-8 people
Available off season clean & cozy townhome. Near historic Lewes and bike trails.
10.0 out of 10, Exceptional, (95)
"Excellent stay! the place is in a great location with lots of functionality, nice decor,clean and a responsive host. Would definitely stay here again!"
Available off season clean & cozy townhome. Near historic Lewes and bike trails.
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

Everything you need to know about Greenwood holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Greenwood holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Greenwood holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Greenwood holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Greenwood. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Greenwood holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Greenwood holiday rentals we have selected for you start as low as NZ$359 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Greenwood rentals

At Expedia, we put the best Greenwood holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Greenwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Greenwood holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Greenwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Historic home, great yard & Walk to Dogfish Head Brewery!: This holiday home rental outside of Greenwood offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

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 Abbott's Mill Nature Center. 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.