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Vacation Homes in Greenwood

Bayfront Cottage with Spectacular Views

10.0 out of 10, Exceptional, (451)
"This is an amazing place for a winter escape (Seems great for other seasons, but we went in the winter). Directly on the beach with access for walks, and bird watching across the street at the wetlands. Hot tub is great, and the night sky views are incredible. House is really comfortable, with a large kitchen and dining area. Short trip to Lewes for dinner or brunch. "
Bayfront Cottage with Spectacular Views

beachfront on the Delaware Bay- beautiful Prime Hook Beach

9.8 out of 10, Exceptional, (109)
"This is my 2nd year staying and it's always excellent and well equipped with everything and anything you need. We will be back again next year! "
beachfront on the Delaware Bay- beautiful Prime Hook Beach

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

10.0 out of 10, Exceptional, (15)
"It was a awesome great comfy house."
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

The Lilly Pad: Big fenced in yard, close to beaches, kayaking and more!

10.0 out of 10, Exceptional, (24)
"My family and I enjoyed our stay! The owners were very generous to us. The property was in a wonderful town close to beaches and Sports at the Beach! Would love to stay there again!"
The Lilly Pad: Big fenced in yard, close to beaches, kayaking and more!

205 Priscilla Circle - New listing with private pool!

8.4 out of 10, Very Good, (6)
"We had a great time at the Priscilla ranch. The pool was spacious and we had fun splashing and grilling!"
205 Priscilla Circle - New listing with private pool!

Family friendly home w/ 360 views of the bay and wild life preserve (sleeps 12)

10.0 out of 10, Exceptional, (63)
"Awesome stay at Bliss at Broadkill beach! Everything was clean and well maintained, and our host was very quick to respond back to any questions we had. Views were amazing from the house and we were able to make so many fun memories going to the beach and using the back dock. Would definitely consider returing for another stay :)"
Family friendly home w/ 360 views of the bay and wild life preserve (sleeps 12)

510 DuPont Avenue - Brand New House In-Town Lewes!

510 DuPont Avenue - Brand New House In-Town Lewes!

Luxury Treehouse with Large Deck

Luxury Treehouse with Large Deck

10 Florida Ave 200Ft to Water Pet Friendly Broadkill Beach Home Bay Block

10.0 out of 10, Exceptional, (43)
"We enjoyed our stay at Manatee Manor. Clean, organized, so close to the beach! We had a wonderful time!"
10 Florida Ave 200Ft to Water Pet Friendly Broadkill Beach Home Bay Block

3BR/4BA Beach Front Property with Spectacular Water Views from Every Room!

10.0 out of 10, Exceptional, (99)
"This was our third stay at this property. It is perfect for our family of four. One of the reasons we keep returning is that we can hear the ocean from the master bedroom. It doesn’t get better than that! We will come back again, which is the measure of an outstanding property. "
3BR/4BA Beach Front Property with Spectacular Water Views from Every Room!

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

10.0 out of 10, Exceptional, (78)
"Family of 12 had a great week at your house. Great location and loved fishing from the dock out back."
EXCLUSIVELY YOURS! Private Beach Path, Double Water Access, and Dog Friendly.

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

10.0 out of 10, Exceptional, (1)
"This was the cutest cottage. It has everything I needed and then some. The host thought of everything to make the stay comfortable."
Charming 2-bedroom bungalow with WiFi, AC in delightful Milton

In-Town Lewes Charm...Steps to the Canal & Hot Tub!

In-Town Lewes Charm...Steps to the Canal & Hot Tub!

Cozy Waterfront Cottage– Dog Friendly & Fully Stocked!

10.0 out of 10, Exceptional, (193)
"Very nice house and quiet surroundings "
Cozy Waterfront Cottage– Dog Friendly & Fully Stocked!

♦︎ Waterfront ♦︎ Pet Friendly ♦︎ Broadkill Beach ♦︎

10.0 out of 10, Exceptional, (91)
"Wonderful property, great location, beautiful views. "
♦︎ Waterfront ♦︎ Pet Friendly ♦︎ Broadkill Beach ♦︎

Beachfront Sunrise - Waterfront house w/ bay and refuge views Sleeps 6-8 people

10.0 out of 10, Exceptional, (168)
"It was amazing, we loved the house and all the amenities. Being right on the beach was great. We also loved having all the birds in the yard."
Beachfront Sunrise - Waterfront house w/ bay and refuge views Sleeps 6-8 people

Casa del Rio, a River House in Millsboro!

9.2 out of 10, Wonderful, (9)
"Great house to come back from a long day out! "
Casa del Rio, a River House in Millsboro!

Gorgeous pano views, Beach Front Access and hot tub! Your peaceful escape!

10.0 out of 10, Exceptional, (26)
"It’s was a beautiful house that’s was perfect for our family/friends trip!"
Gorgeous pano views, Beach Front Access and hot tub! Your peaceful escape!

Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

9.8 out of 10, Exceptional, (11)
"We loved the property and the excellent way the owners took care of it"
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

Village of Five Points townhouse with community pool, gym, and tennis access

10.0 out of 10, Exceptional, (1)
"House was exactly what we budgeted for. Loved the back patio. Comfortable beds. Parking outside the front doors. The kitchen was very nice too. Did not have a ton of amenities, but everything was sufficient. "
Village of Five Points townhouse with community pool, gym, and tennis access
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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