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Vacation Homes in Greenwood

Captain's Quarters

9.8 out of 10, Exceptional, (98)
"This our second time staying here and we absolutely love it! Looking forward to staying here again in May 2026. "
Captain's Quarters

Bayfront Cottage with Spectacular Views

10.0 out of 10, Exceptional, (460)
"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

Cozy Waterfront Cottage– Dog Friendly & Fully Stocked!

10.0 out of 10, Exceptional, (203)
"A nice peaceful, beautiful getaway that is still close to Rehoboth!"
Cozy Waterfront Cottage– Dog Friendly & Fully Stocked!

Prime Hook Retreat - Amazing View of the Refuge - Beach Access Across the Street

10.0 out of 10, Exceptional, (38)
"Clean, quiet and great location "
Prime Hook Retreat - Amazing View of the Refuge - Beach Access Across the Street

Cozy home minutes from Lewes and Rehoboth Beach

10.0 out of 10, Exceptional, (34)
"Had a good stay. Was very clean."
Cozy home minutes from Lewes and Rehoboth Beach

Great Escape ~Unique Beach Views ~ Right on the Water~Child Items ~ Linens

10.0 out of 10, Exceptional, (116)
"This home is beautiful. Incredible views from all levels. It was clean and well stocked with everything you could need to feel at home. Plenty of beach toys and chairs for everyone. The kitchen was a delight with all a chef could desire. The owners Tess & Andy were wonderful and highly communicative. Lots of TLC put into this home. We would highly recommend. "
Great Escape ~Unique Beach Views ~ Right on the Water~Child Items ~ Linens

Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!

2.0 star property
10.0 out of 10, Exceptional, (14)
Welcome to COASTAL SERENITY - Your Ultimate Beachfront Escape!

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

10.0 out of 10, Exceptional, (176)
"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

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

9.8 out of 10, Exceptional, (23)
"We loved this property and hopefully will be back next year. Was amazing having room to spread out and such a nice clean house! "
Backroad Getaway -Brand New 3-bedroom retreat near Sports at the Beach & DE Turf

Lee's Place Brand New 2BR Townhouse w/free parking

9.4 out of 10, Exceptional, (28)
"It was a great option for our Lacrosse weekend!"
Lee's Place Brand New 2BR Townhouse w/free parking

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

Luxury Treehouse with Large Deck

10.0 out of 10, Exceptional, (9)
"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

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

10.0 out of 10, Exceptional, (95)
"Our stay was lovely! The house was clean, spacious for our family (5 adults, 2 kids), the beds were clean and it was in a quiet neighborhood. We would stay here again! "
Clean & cozy townhome. Quick access to trails & historic Lewes. 5 mins to beach.

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

8.8 out of 10, Excellent, (23)
"This is a beautiful property. I found it quite appropriate for a family vacation. It was quite spacious. We loved the deck area. All worked well for us. I loved the proximate to the Beach."
3+ Night Rentals Allowed - Large Pet Friendly Home with Fenced-In Back Yard

Dog Friendly Home, Views of the Delaware Bay & Prime Hook National Refuge, Dock

9.4 out of 10, Exceptional, (58)
"It was a nice house in a quiet area and great location, with the Broadkill sound on one side and the beach nearby on the other. The public beach access was just across the street and a short walk in to the sand and water!"
Dog Friendly Home, Views of the Delaware Bay & Prime Hook National Refuge, Dock

Delaware Beachfront Private Getaway on the Bay

9.8 out of 10, Exceptional, (190)
"Wonderful place for nature, peace, and quiet. Beautiful sunrises every morning. A great getaway."
The price is SAR 1,336
SAR 2,770 total
includes taxes & fees
18 Sep - 19 Sep
Delaware Beachfront Private Getaway on the Bay

Wind Song Getaway on the Beach

9.8 out of 10, Exceptional, (33)
"This home is beautiful! Host was responder quickly "
Wind Song Getaway on the Beach

Your vacation home of 4200sq ft Millsboro.Pet friendly,Private Pool Jacuzzi etc

2.0 star property
9.6 out of 10, Exceptional, (7)
"Quick response and good communication. How’s was nice and spacious."
Your vacation home of 4200sq ft Millsboro.Pet friendly,Private Pool Jacuzzi etc

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

10.0 out of 10, Exceptional, (33)
"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!

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (38)
"We really enjoyed our stay. The house has everything needed and the sunrises are beautiful."
Stylish Home on the Choptank River (with Tidal 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