Greenwood vacation rentals

We found 9 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: Enjoy activities like hiking, biking, and picnicking in urban parks and natural settings.
  • Lake Greenwood: Relax by the serene lake, perfect for fishing and leisurely strolls.
  • Family-Friendly Attractions: Explore local attractions that cater to both children and adults.
  • Horse Racing Venues: Experience the excitement of horse racing in nearby venues.
  • Diverse Accommodation Options: Choose from cozy cottages to modern condos for a comfortable stay.

Popular types of accommodation in Greenwood

Planning a getaway to Greenwood? You're in for a treat. Discover the charm of this delightful destination with our selection of vacation rentals. From spacious houses and cozy cottages to modern condos and apartment rentals, there’s something for everyone. Explore your options for Greenwood vacation rentals and find the perfect vacation home that suits your needs. Start your adventure today.

  • Houses: The top choice for travelers seeking a home-like atmosphere, these rentals offer comfort and amenities for families or groups in Greenwood.
  • Cottages: Charming and cozy, cottages provide a quaint retreat, perfect for those looking to relax in a serene environment.
  • Condos: These modern accommodations combine convenience and style, making them ideal for travelers wanting easy access to local attractions.
  • Apartments: Featuring essential living spaces, apartments are a practical option for those seeking flexibility and independence during their stay.
  • Villas: Spacious and luxurious, villas are perfect for those wanting an upscale vacation experience with stunning surroundings.**

Top attractions near Greenwood

Greenwood, Delaware, offers a delightful mix of outdoor adventures and family-friendly attractions, making it perfect for romantic getaways and vacations. You can explore local points of interest such as urban parks, horse racing venues, and nearby golf courses. For a more enriching experience, consider visiting national parks or indulging in recreational activities that highlight the area's charm and beauty.

  • Harrington Raceway and Casino: Enjoy an exhilarating day of horse racing and gaming at this lively venue. With thrilling races and a variety of gaming options, it's perfect for those seeking adventure and entertainment just 7 miles from Greenwood.
  • Delaware State Fairgrounds: A fantastic spot for family fun, this fairground hosts various events and festivals throughout the year. Experience outdoor activities and local culture, all while being just 7 miles from Greenwood.
  • Bayhealth Hospital-Sussex Campus: Although primarily a medical center, this facility represents community wellness and family care. It plays a vital role in the local healthcare system, located 12 miles from Greenwood.

Things to do recommended for couples

For a romantic getaway in Greenwood, enjoy a cozy picnic at the serene Redden State Forest, followed by a wine tasting at a local vineyard. Don’t miss a sunset stroll along the scenic trails, perfect for capturing unforgettable moments together.

Things to do recommended for families

Families visiting Greenwood, Delaware, can explore the fun at the Delaware State Fair, enjoy outdoor activities at the nearby Lums Pond State Park, and discover local history at the Greenwood Museum, providing engaging experiences for kids and adults alike.

Things to do recommended for groups

Explore the scenic beauty of the Delaware countryside with a group hike in the nearby Redden State Forest or enjoy a fun-filled day at the Delaware State Fair, featuring local vendors, live entertainment, and exciting rides.

*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

If you're traveling with a group, your family, pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Greenwood with a group: Think about how many bedrooms you'll require, as well as any amenities like a fully equipped kitchen or outdoor area for group get-togethers. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Greenwood with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with ensuring access to 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 families, a getaway isn’t truly special without their furry companions. If you can relate, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that all family members feel comfortable and at home.
  • Planning for a long term stay visiting Greenwood: If you're searching for vacation rentals with great deals for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. You might also want to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Greenwood

Greenwood, Delaware, is the perfect destination for outdoor enthusiasts and families alike. Explore the serene Lake Greenwood and enjoy a relaxing getaway surrounded by friendly locals and rich history. Nearby cities offer a blend of business vibes and family-friendly atmospheres, making it an ideal spot for romance or adventure. Experience the charm of Greenwood and its surrounding areas for a memorable vacation filled with exploration and relaxation.

  • Delaware Beaches: Located 16 miles away from Greenwood, Delaware Beaches is a popular destination for those seeking outdoor adventures and romantic getaways. This area is known for its stunning shoreline, lively boardwalks, and charming shopping areas. Visitors can enjoy a variety of activities including sunbathing on the beach, exploring local boutiques, and indulging in fresh seafood at nearby restaurants. The family-friendly atmosphere makes it a fantastic spot for all ages, with attractions like the expansive beach and scenic esplanade offering plenty of options for relaxation and fun.
  • Milford: Just 11 miles from Greenwood, Milford is a vibrant city ideal for families and outdoor enthusiasts. With its beautiful recreation parks and welcoming boardwalk, Milford provides a perfect setting for picnicking, walking, or playing sports. The city boasts a lovely recreational area that is perfect for family outings. Local landmarks include beautiful parks and family-friendly beaches, making it a great place to immerse yourself in nature while enjoying the warm community spirit.
  • Bridgeville: A mere 5 miles from Greenwood, Bridgeville is a charming city that attracts travelers looking for outdoor activities, romantic escapes, and family fun. The area features a delightful boardwalk and recreational spaces, as well as golf courses for those looking to tee off. Nearby attractions include pristine beaches, the picturesque esplanade, and the expansive national state park, offering ample opportunities for hiking and wildlife observation. The combination of natural beauty and community engagement makes Bridgeville a worthwhile stop on your vacation.

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

Are you interested in saving on your next adventure? Being flexible with your travel dates can often lead to better deals, as prices tend to vary. Additionally, opting for a longer stay can help you secure significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of vacation rental.

Unlock savings with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash on your booking. Being the planner really pays off. By enrolling in our travel rewards program, One Key, you can immediately access member discounts and earn OneKeyCash on eligible reservations. Sign up today and begin enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient platform for you to plan new adventures, manage your ongoing arrangements, or review and organize your bookings. Your saved or reserved properties are neatly categorized into Potential, Upcoming, or Current Trips. To check out the 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:

  • Rookery Golf Club (17.4 mi / 28 km)
  • T.S. Smith & Sons (4 mi / 6.4 km)
  • Hooper's Landing Golf Course (11.6 mi / 18.7 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)
  • Milton Memorial Park (15.3 mi / 24.6 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)

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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