Greenwood Vacation Rentals

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Our top choices for Greenwood vacation rentals

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 reviews)
"Great location, peaceful, clean, quaint & accommodating hosts"
United States
Michelle T.
The price is CA $230
CA $405 total
includes taxes & fees
May 30 - May 31
EXTRA CLEAN In-Law-Suite - QUEEN bed, High Speed WIFI, Smart TV & Much More!

GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE

GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE
Milford
10.0 out of 10, Exceptional, (138 reviews)
"Clean, pet friendly, nice beach."
United States
Ned J.
The price is CA $436
CA $716 total
includes taxes & fees
Jun 3 - Jun 4
GORGEOUS, RECENTLY RENOVATED, WATERFRONT COTTAGE

Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (5 reviews)
"My husband and I stayed for two nights. The oasis makes you feel like you’re vacationing in the Caribbean. The camper is clean and comfortable for two people. Everything was perfect and cannot wait to return!"
United States
Marleen M.
The price is CA $221
CA $353 total
includes taxes & fees
Jun 9 - Jun 10
Mini Aruba RV/Glamping Tent

Serene beach cottage a short walk from beautiful Broadkill Beach. Pet friendly!

Serene beach cottage a short walk from beautiful Broadkill Beach. Pet friendly!
Milton
9.8 out of 10, Exceptional, (30 reviews)
"Comfortable and close to the beach - perfect!"
United States
Saundra P.
The price is CA $354
CA $733 total
includes taxes & fees
Jun 1 - Jun 2
Serene beach cottage a short walk from beautiful Broadkill Beach. Pet friendly!

Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (12 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is CA $496
CA $852 total
includes taxes & fees
Jun 1 - Jun 2
Turnbridge Manor

Poe Themed Home Close to Beaches and DE Turf

Poe Themed Home Close to Beaches and DE Turf
Milford
9.6 out of 10, Exceptional, (9 reviews)
"Loved the Poe themed quirky charm. Convenient parking. We were attending a soccer tournament and it was a super easy 11 minute drive to DE Turf. We love old houses and it felt like our previous home in New Orleans. Cat was very responsive after an initial problem with the Vrbo app. Would stay again!"
United States
John
The price is CA $223
CA $382 total
includes taxes & fees
May 31 - Jun 1
Poe Themed Home Close to Beaches and DE Turf

Lewes Beach town Condo on 1st Floor!

Lewes Beach town Condo on 1st Floor!
Villages of Five Points
10.0 out of 10, Exceptional, (23 reviews)
"We had a great stay. The place was prefect! "
United States
Lisa S.
The price is CA $225
CA $519 total
includes taxes & fees
Jun 3 - Jun 4
Lewes Beach town Condo on 1st Floor!

Escape to our spacious & serene 3-bedroom home with stunning bay views.

Escape to our spacious & serene 3-bedroom home with stunning bay views.
Milford
9.8 out of 10, Exceptional, (21 reviews)
"Great location with tons of space, being able to bring our dog along was so wonderful. Unfortunately the plumbing to the outdoor shower was broken which we were looking forward to using but otherwise everything was as expected! "
United States
Calvin M.
The price is CA $254
CA $588 total
includes taxes & fees
Jun 2 - Jun 3
Escape to our spacious & serene 3-bedroom home with stunning bay views.

Cozy home in Milford/Harrington for relaxing stays!

Cozy home in Milford/Harrington for relaxing stays!
Harrington
The price is CA $272
CA $320 total
includes taxes & fees
May 31 - Jun 1
Cozy home in Milford/Harrington for relaxing stays!

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!
Frederica
10.0 out of 10, Exceptional, (21 reviews)
"Super cute and clean place, the host was very responsive to my questions. "
United States
Gosha R.
The price is CA $103
CA $271 total
includes taxes & fees
Jun 2 - Jun 3
Totally Remodeled Cozy Apartment. 2.5 miles to Delaware Turf!

Welcoming 3-bedroom house with AC in charming Milford.

Welcoming 3-bedroom house with AC in charming Milford.
Milford
10.0 out of 10, Exceptional, (1 review)
"The guys went to the race and they were very happy with the location the price and the people were very nice to deal with"
United States
debra h.
The price is CA $448
CA $690 total
includes taxes & fees
Jun 9 - Jun 10
Welcoming 3-bedroom house with AC in charming Milford.

1st Floor Beach-town Condo. We are Pet Friendly!

1st Floor Beach-town Condo. We are Pet Friendly!
Villages of Five Points
9.8 out of 10, Exceptional, (37 reviews)
"I had a great interaction with the host and the rooms were very clean and comfortable and it also has a great kitchen with everything you would need and most importantly the area is extremely nice and very quiet and it was perfect for walking our dog, also the Fish on restaurant and the French bakery and Arena’s are as good as it gets! Looking forward to going back in the near future!"
United States
Patrick D.
The price is CA $397
CA $724 total
includes taxes & fees
Jun 15 - Jun 16
1st Floor Beach-town Condo. We are Pet Friendly!

Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5

Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5
Dover
10.0 out of 10, Exceptional, (1 review)
"Our time here was an attraction in itself. There were so many small details. I won't mention all of them as I don't want to spoil the surprise but one of our favorites was a telescope pointed towards an ocean piling where birds frequently perch. The house felt interactive and playful. There were snacks and beverage options (including tea, coffee, water, and even other surprises) available. Very clean. One consideration is the stairscase. I would advise caution for those with mobility issues (bad...
United States
Alex L.
The price is CA $330
CA $535 total
includes taxes & fees
May 31 - Jun 1
Tiny Bay House on Delaware Bay / 2 min walk to the beach / Sleeps 5

Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape

Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape
Lincoln
10.0 out of 10, Exceptional, (1 review)
"Thank you, we had a very pleasant stay"
United States
andy O.
The price is CA $154
CA $299 total
includes taxes & fees
May 31 - Jun 1
Cozy Cabin Getaway at Gum Branch Acres – Perfect for a Quiet Escape

Cozy Unit in Milford, Delaware -Close to DE Turf

Cozy Unit in Milford, Delaware -Close to DE Turf
Milford
10.0 out of 10, Exceptional, (3 reviews)
"The unit is tiny but knowing we wouldn’t be spending much time there, it was fine for our use. I liked that we could walk to locations in town. Her directions for use were very clear and precise."
United States
Rebecca N.
The price is CA $164
CA $310 total
includes taxes & fees
May 31 - Jun 1
Cozy Unit in Milford, Delaware -Close to DE Turf

Spacious Condo•Pond Views•Centrally located

Spacious Condo•Pond Views•Centrally located
Plantations East
9.8 out of 10, Exceptional, (29 reviews)
"Stayed at this VRBO before. Great location. Pet friendly. "
United States
Betty L.
The price is CA $129
CA $430 total
includes taxes & fees
Jun 1 - Jun 2
Spacious Condo•Pond Views•Centrally located

Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!

Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!
Milford
The price is CA $286
CA $417 total
includes taxes & fees
Jun 3 - Jun 4
Stunning Home: DE Turf Complex 2 min away and Gateway to the Beaches!

360 Water Views I Steps to Beach I Rooftop & Screened Deck I Elevator I Dog Welc

360 Water Views I Steps to Beach I Rooftop & Screened Deck I Elevator I Dog Welc
Milton
10.0 out of 10, Exceptional, (2 reviews)
"House was beautiful! Clean, quiet location. Short walk to beach and local store. "
United States
Taylor G.
The price is CA $1,054
CA $1,882 total
includes taxes & fees
Jun 12 - Jun 13
360 Water Views I Steps to Beach I Rooftop & Screened Deck I Elevator I Dog Welc

Cozy Coastal Retreat - Community Pool, Close to Lewes and Rehoboth Beaches

Cozy Coastal Retreat - Community Pool, Close to Lewes and Rehoboth Beaches
Lewes
10.0 out of 10, Exceptional, (6 reviews)
"We thoroughly enjoyed our stay"
United States
Jonathan D.
The price is CA $379
CA $670 total
includes taxes & fees
Jun 14 - Jun 15
Cozy Coastal Retreat - Community Pool, Close to Lewes and Rehoboth Beaches

New 3‑BR Ranch by DE Turf & Beaches

New 3‑BR Ranch by DE Turf & Beaches
Lincoln
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful accommodations that are very comfortable. We would stay there again."
United States
Beth S.
The price is CA $158
CA $402 total
includes taxes & fees
Jun 1 - Jun 2
New 3‑BR Ranch by DE Turf & Beaches
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Greenwood. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Greenwood?

Yes, there are vacation rentals near popular local attractions in Greenwood, or you can choose a secluded option if you'd like a relaxing place to 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 vacation rentals that Greenwood has to offer?

Secluded Beach home with amazing views. : Visitors like this Greenwood vacation home rental. It is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 Second Street Players - Riverfront Theatre are a couple of places you'll find in the larger area.

What are vacation rentals like in Greenwood?

Vacation rentals are private accommodations you can stay in for a few days or a quick weekend in Greenwood. Vacation rentals offer extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and bustling concierge desks while still allowing you to travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a small group gathering.