Greenwood vacation rentals

We found 11 vacation rentals — enter your dates for availability

Scroll through and select from vacation rentals in Greenwood to find one that's perfect for your trip. Whether you’re staying in a vacation home with family, friends, or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a hot tub. Whatever you're looking for, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

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Find out more about Greenwood

Why visit Greenwood

  • Outdoor Adventures: Explore various national and urban parks, perfect for hiking, picnicking, and enjoying nature.
  • Family-Friendly Activities: Enjoy attractions suitable for all ages, ensuring memorable experiences for families.
  • Charming Accommodations: Choose from private vacation homes, cozy condos, and charming cottages tailored to your needs.
  • Rich History: Visit nearby neighborhoods filled with historical significance and charming character.
  • Friendly Atmosphere: Experience the welcoming community and beautiful views that make Greenwood special.

Popular types of accommodation in Greenwood

If you're exploring vacation rentals in Greenwood, you're in for a treat. Our most popular accommodations include houses, cozy condos, and charming cottages. Whether you're looking for a pet-friendly house rental or a fully-equipped vacation home, we have options that cater to all your needs. Enjoy top amenities and experience the comfort and convenience of staying in Greenwood.

  • Houses: The top choice for visitors in Greenwood, offering spacious and comfortable accommodations ideal for families and groups.
  • Condos: A popular option for those seeking modern amenities and a convenient location, perfect for couples and small families.
  • Cottages: Charming and cozy, these rentals provide a quaint escape for those looking for a peaceful retreat.
  • Apartments: A practical choice for travelers wanting a home-like setting with easy access to local attractions.
  • Villas: Luxurious and spacious, villas cater to those looking for an upscale vacation experience.**

Top attractions near Greenwood

Greenwood, Delaware, is perfect for outdoor enthusiasts and families seeking a romantic getaway. Visitors can explore a variety of attractions, including national and urban parks, as well as fairgrounds and showgrounds. With its blend of natural beauty and city experiences, Greenwood offers something for everyone, making it an ideal destination for travelers looking to enjoy the great outdoors or family-friendly activities.

  • Delaware State Fairgrounds: Located 7 miles from Greenwood, this vibrant fairground offers a family-friendly atmosphere with various events, including the annual Delaware State Fair, featuring rides, games, and local cuisine.
  • Bridgeville Historical Society Museum: Just 4 miles away, this museum immerses you in the rich history and culture of the area, showcasing artifacts and exhibits that tell the story of Bridgeville and its heritage.
  • Abbott's Mill Nature Center: Situated 8 miles from Greenwood, this eco-friendly center features beautiful trails, wildlife viewing, and educational programs focused on environmental conservation and sustainability.

Things to do recommended for couples

For a romantic getaway in Greenwood, consider dining at The Hen House, located 16 miles away. This charming restaurant offers a cozy atmosphere perfect for couples, blending city and family vibes with a touch of romance. Enjoy a delightful meal and create lasting memories together.

Things to do recommended for families

Your family will love the DE Turf Sports Complex for its wellness vibes and recreational activities, just 15 miles from Greenwood. For some energetic fun, head to Sports at the Beach, also 15 miles away, where you can enjoy various sports in a lively atmosphere.

Things to do recommended for groups

Explore local flavors at T.S. Smith & Sons, just 4 miles from Greenwood. Enjoy craft brews with a romantic vibe at Dogfish Head Craft Brewery, 15 miles away. For a cultural experience, catch a show at the Second Street Players - Riverfront Theatre, located 11 miles from Greenwood.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Greenwood

When planning your trip, whether you're traveling with a group, family, pets, or seeking extended stays, be sure to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to Greenwood with a group: Think about how many bedrooms you'll require, along with any additional features like a complete kitchen or outdoor area for group activities. Luckily, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to Greenwood with young kids: Traveling with young kids can be tough. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Greenwood: For many, a family vacation isn’t truly fulfilled without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortably at home.
  • Planning for a long term stay visiting Greenwood: If you're in search of vacation rentals that offer great deals for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Greenwood

Greenwood, Delaware, offers a perfect getaway for outdoor enthusiasts and families alike. Experience the heart of Greenwood with its friendly atmosphere and excellent views. Enjoy relaxing moments in nearby neighborhoods rich in history and charm. Whether you're seeking a romantic escape or a family-friendly adventure, Greenwood has something for everyone, making it an ideal destination for your vacation.

  • Delaware Beaches: Located 16 miles from Greenwood, Delaware Beaches is the perfect destination for those seeking outdoor adventures and a romantic getaway. With its picturesque boardwalk, vibrant shopping areas, and beautiful recreational spots, visitors can enjoy a leisurely day soaking up the sun or engaging in water activities. The local landmarks, including the stunning beaches and the lively esplanade, provide ample opportunities for family fun and relaxation. Whether you’re strolling along the shore or indulging in local cuisine, Delaware Beaches offers a memorable coastal experience.
  • Milford: Just 11 miles away from Greenwood, Milford is a charming city known for its family-friendly atmosphere and outdoor attractions. The city's recreation park and boardwalk are popular spots for both locals and tourists, offering activities that cater to all ages. Milford’s nearby beach and sports facility stadium make it an ideal location for those looking to blend leisure with excitement. With its warm community vibe and beautiful landscapes, Milford invites visitors to connect with nature and enjoy quality time with loved ones.
  • Bridgeville: Only 5 miles from Greenwood, Bridgeville is a quaint city that offers a delightful mix of outdoor activities and romantic settings. Visitors can explore the local boardwalk, recreation parks, and pristine recreational areas, making it an excellent spot for families and couples alike. The close proximity to stunning beaches and the national state park enhances the area’s appeal, providing opportunities for hiking, picnicking, and enjoying the great outdoors. Bridgeville’s welcoming atmosphere makes it a perfect addition to your travel itinerary.

Best time to go to Greenwood

If you're planning a trip to Greenwood, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.8°F (2.1°C)Light RainMostly SunnyModerately LowSlightly Low
February38.3°F (3.5°C)Light RainMostly SunnyAverageSlightly Low
March44.2°F (6.8°C)Light RainMostly SunnyAverageSlightly Low
April54.3°F (12.4°C)Light RainMostly SunnyAverageAverage
May63.1°F (17.3°C)Light RainMostly SunnyAverageAverage
June72.0°F (22.2°C)Light RainMostly SunnyModerately HighSlightly High
July77.2°F (25.1°C)Light RainMostly SunnyModerately HighSlightly High
August75.6°F (24.2°C)Light RainMostly SunnyModerately HighSlightly High
September70.0°F (21.1°C)Light RainMostly SunnyAverageAverage
October60.3°F (15.7°C)Light RainMostly SunnyAverageAverage
November48.9°F (9.4°C)Light RainMostly SunnyModerately LowAverage
December41.9°F (5.5°C)Light RainMostly SunnyModerately LowAverage

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can change significantly. Additionally, extending your stay can lead to substantial savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

Plan your group getaway by booking an eligible Vrbo and earn OneKeyCash on your reservation. Being the planner really pays off. By becoming a member of our travel rewards program, One Key, you'll gain immediate access to exclusive member savings and the opportunity to earn and redeem OneKeyCash on qualifying bookings. Sign up today and begin your journey to savings.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up right where you left off, or manage and organize your travel plans. You can easily find the properties you've saved and booked under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Explore the beachside setting in Greenwood

The beaches and surrounding scenery provide a peaceful ambiance to your vacation home in Greenwood. This city's restaurants, sporting events and shopping draw many visitors. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Greenwood

Do you want to discover attractions to see while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Greenwood a fun place to get away. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Hooper's Landing Golf Course (11.6 mi / 18.7 km)
  • Rookery Golf Club (17.4 mi / 28 km)
  • T.S. Smith & Sons (4 mi / 6.4 km)
  • South Rookery Golf Course (17.4 mi / 28 km)

Exploring the natural landscape of Greenwood

Whether you're looking for adventure or just want to appreciate the scenery, Greenwood is a great place to get outside. Here are a few of the area's noteworthy sights, all within 30 miles (48.2 km) of the city center:

  • DE Turf Sports Complex (15.1 mi / 24.3 km)
  • Slaughter Beach (17.1 mi / 27.5 km)
  • Prime Hook National Wildlife Refuge (17.9 mi / 28.8 km)
  • Prime Hook Beach (19.1 mi / 30.7 km)
  • Broadkill Beach Beaches (20.5 mi / 33 km)
  • Abbott's Mill Nature Center (8.2 mi / 13.3 km)

Traveling to and around Greenwood

The nearest airport is in Georgetown, DE (GED-Sussex County), located 14.7 mi (23.6 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Easton, MD (ESN-Easton - Newnam), which is 25.5 mi (41 km) away.

Frequently asked questions

What is the best area to stay in Greenwood, Delaware, United States of America when booking a vacation rental?
When considering the best area to stay in Greenwood, Delaware, a great option is the historic downtown neighborhood. This area captures the charm of small-town living, with cozy vacation rentals that offer an inviting space. You can enjoy easy access to local attractions like the nearby scenic parks, which are superb for outdoor activities such as hiking and picnicking. Additionally, the downtown area is close to quaint shops and delightful eateries that showcase the local flavor.

Another appealing neighborhood is the countryside surrounding Greenwood, where you can find properties located among beautiful landscapes. This area is ideal for those seeking tranquility and a connection to nature. It's also conveniently located near popular attractions like the Delaware Agricultural Museum, where visitors can learn about the state's rich farming history.
How much does it cost to rent a vacation home in Greenwood?
Prices for vacation rentals in Greenwood vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Greenwood to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Greenwood vacation house rentals?
You can find great discounts on house rentals in Greenwood on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Greenwood?
For renting a beach house in Greenwood, travelers should consider the nearby coastal areas of Delaware, particularly Rehoboth Beach and Dewey Beach, which are just a short drive away. Rehoboth Beach is known for its vibrant boardwalk, charming shops, and a variety of dining options. In this area, vacation rentals often feature amenities such as outdoor decks, pools, and easy beach access, making them ideal for families and larger groups. Many properties also offer modern kitchens and spacious living areas, great for entertaining after a day at the beach.

Dewey Beach, located just south of Rehoboth, offers a more laid-back atmosphere with an emphasis on water sports and nightlife. Beach houses here frequently come equipped with amenities like beach gear, outdoor grills, and proximity to local bars and restaurants. The sandy shores are just a short walk away, and some rentals even provide private beach access.

Additionally, the scenic Cape Henlopen State Park nearby is worth exploring, offering hiking trails, picnic areas, and pristine beaches. Rentals in this region may include features such as bicycles for exploring the park and outdoor showers for rinsing off after a day spent at the beach.
What is the most popular type of vacation rental accomodation in Greenwood?
In Greenwood, Delaware, vacation houses are quite popular, with several available in the area. These homes typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups seeking comfort and convenience. Many of these properties are located in peaceful settings, providing a relaxing atmosphere for guests. Additionally, there are several mobile homes and cabins available, offering unique options for travelers looking for a different experience. Mobile homes often come with outdoor seating areas, while cabins may feature rustic charm and proximity to nature.
Are there any family house rentals in Greenwood?
In Greenwood, Delaware, there are several family-friendly house rentals available, making it an excellent choice for groups looking to enjoy a peaceful getaway. The area features a variety of homes that often include spacious living rooms, fully equipped kitchens for preparing meals together, and outdoor areas great for kids to play. Many properties also come with amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay.

Visitors can explore nearby attractions like the picturesque Trap Pond State Park, where families can enjoy hiking, biking, and picnicking. Additionally, the charming downtown area offers local shops and eateries that reflect the unique character of the region.
Can I find long-stay vacation rentals in Greenwood?
A long-stay vacation rental in Greenwood is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there any remote work vacation rentals in Greenwood?
In Greenwood, Delaware, there are several vacation rentals that cater to remote work needs. These properties typically offer convenient amenities such as free Wi-Fi, ensuring that guests can stay connected while enjoying their stay. Many rentals include dedicated workspaces, allowing travelers to set up their laptops comfortably.

The town itself is surrounded by charming rural landscapes and is close to local attractions, making it a peaceful environment for working remotely. Additionally, guests can expect properties with comfortable living areas, full kitchens for meal preparation, and sometimes outdoor spaces for relaxation after a productive workday. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Greenwood vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Greenwood with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Greenwood?
In Greenwood, popular rental amenities include kitchens, which allow guests to prepare their own meals conveniently. Many properties also feature porches or lanais, providing a lovely space to relax outdoors. For families traveling with young children, some rentals offer travel cribs and a selection of books specifically for children, ensuring that little ones are entertained. Additionally, coffee and tea makers are commonly found in these rentals, suiting guests who enjoy a warm beverage in the comfort of their stay.
When is the best time to visit Greenwood for a vacation rental?
The best time to visit Greenwood for a vacation rental is during the peak season from June to August, with July being the most popular month. This vibrant period draws travelers, eager to enjoy the warm weather and outdoor activities that the region has to offer. With temperatures averaging in the mid-70s to low 90s Fahrenheit, it's superb for exploring local parks, attending community events, or simply relaxing in the sun.

During these summer months, visitors can immerse themselves in the lively option of Greenwood, where various festivals and outdoor gatherings take place. The charming local community is welcoming, making it an ideal time for travelers seeking both adventure and a sense of connection.

If you're looking for a more budget-friendly option, consider planning your visit in December. While this is a quieter time in Greenwood, it offers a unique charm with holiday festivities and a peaceful ambiance, superb for those who enjoy a slower pace.

Ultimately, your choice of when to visit Greenwood can enhance your experience based on what you seek, whether it's the lively summer energy or the serene beauty of winter.
How early should I book a Greenwood vacation rental?
Book your Greenwood vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Greenwood, Delaware, United States of America?
In Greenwood, Delaware, visitors can enjoy a range of attractions that highlight the area's charm and natural beauty. The nearby Trap Pond State Park offers opportunities for hiking, kayaking, and birdwatching, making it a great spot for outdoor enthusiasts. Within the park, the scenic pond and lush woodlands provide a serene backdrop for picnics and leisurely strolls.

Additionally, the town hosts several local events and festivals throughout the year, showcasing the community's agricultural heritage and local crafts. The historic downtown area features quaint shops and eateries that reflect the small-town atmosphere.
Can I change or cancel my Greenwood home rental booking on Vrbo?
To find Greenwood vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Greenwood vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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