Greenwood holiday lettings

We found 12 holiday rentals — enter your dates for availability

Scroll through and select from holiday rentals in Greenwood to find one that's perfect for your trip. Whether you’re staying in a holiday home with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a washer and dryer. At the end of the day, you'll be able to choose a property to rent for everyone's needs, including accessible or non-smoking choices.

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Why visit Greenwood

  • Outdoor Adventures: Enjoy a myriad of activities in national and urban parks, perfect for nature lovers.
  • Family-Friendly Attractions: Discover a range of attractions that cater to families, ensuring fun for all ages.
  • Charming Neighbourhoods: Explore picturesque neighbourhoods rich in history and a welcoming atmosphere.
  • Varied Accommodations: Choose from private vacation homes, delightful cottages, or modern condos for a comfortable stay.
  • Beachside Relaxation: Unwind in nearby beach settings that offer a tranquil escape for romantic getaways.

Popular types of accommodation in Greenwood

If you're contemplating a getaway to Greenwood, we have just the right options for you. Our most sought-after types of accommodation include houses, charming cottages, and modern condos. Whether you're looking for Greenwood apartments, spacious house rentals, or comfortable townhomes, we offer a variety of homes for rent that cater to your needs. Enjoy your stay with transparency, savings, and peace of mind.

  • Houses: The top choice for visitors in Greenwood, these homes offer spacious and comfortable stays, perfect for families or groups.
  • Cottages: A charming alternative, these quaint retreats provide a cosy atmosphere for couples and smaller families.
  • Condos: Ideal for those seeking a modern stay, condos combine convenience with amenities in a shared setting.
  • Apartments: Offering flexibility and self-catering options, apartments are a popular choice for independent travellers.
  • Villas: For a touch of luxury, villas provide upscale accommodation with ample space and often stunning surroundings.**

Top attractions near Greenwood

Greenwood, Delaware, is an ideal destination 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. The local points of interest offer a diverse experience, ensuring there's something for everyone, whether you're looking to enjoy nature or engage in city activities. A trip to Greenwood promises memorable moments and delightful adventures for all travellers.

  • Delaware State Fairgrounds: A vibrant venue just 4.3km from Greenwood, perfect for families seeking outdoor fun. Enjoy various events and fairs that bring the community together, showcasing local culture and agriculture.
  • Bridgeville Historical Society Museum: Located 2.5km away, this museum offers a glimpse into the region's rich history and heritage, featuring fascinating exhibits that celebrate local culture.
  • Abbott's Mill Nature Center: Situated 5.0km from Greenwood, this eco-friendly centre combines nature with sustainability, providing an educational experience amidst beautiful surroundings.

Things to do recommended for couples

If you're seeking a romantic escape in Greenwood, consider dining at The Hen House, located 9.9km away. This charming restaurant offers a delightful atmosphere perfect for couples, blending family warmth with a touch of romance, making it an ideal spot for a memorable meal together.

Things to do recommended for families

Families visiting Greenwood can enjoy sports at the Beach, a vibrant facility 9.3km away, or unwind at the Seaford Sports Complex, a recreational park located 6.8km from Greenwood, perfect for wellness and relaxation.

Things to do recommended for groups

Groups visiting Greenwood can enjoy local experiences such as shopping at T.S. Smith & Sons, exploring the romantic vibes at Dogfish Head Craft Brewery, and taking in a performance at the Second Street Players - Riverfront Theatre, which offers a delightful mix of entertainment and culture.

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

When planning your trip, whether you're travelling with a group, a family, or bringing along your pets, or even considering longer stays, it's important to prioritise the right filters. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Greenwood with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options and much more on Vrbo.
  • Traveling to Greenwood with young kids: Travelling with young children can be quite demanding. It's essential to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, considering how close you are to family-friendly attractions can be beneficial.
  • Taking your pets with you to Greenwood: For many, a family holiday wouldn’t feel complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Greenwood: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can easily discover and save on monthly rentals. Don't forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Greenwood

Greenwood, Delaware, offers a delightful blend of outdoor adventures and family-friendly attractions. With charming neighbourhoods and nearby cities, visitors can immerse themselves in a welcoming atmosphere filled with history and relaxation. Explore family homes for rent, enjoy the beachside setting, or discover new homes in the area. Whether you're seeking a romantic getaway or a fun-filled family holiday, Greenwood and its surroundings provide the perfect backdrop for an unforgettable experience.

  • Milford: Milford is a charming city located 6.8km from Greenwood, offering visitors a delightful outdoor and family-friendly experience. The city is known for its picturesque recreation park and vibrant boardwalk, perfect for leisurely strolls and enjoying the local scenery. Milford’s recreational areas provide ample opportunities for sports and relaxation, making it an excellent spot for families. Nearby, you can find beautiful beaches and local parks that invite exploration and outdoor activities, ensuring a memorable visit for all.
  • Delaware Beaches: Situated 9.9km from Greenwood, the Delaware Beaches are a popular destination for those seeking a romantic and outdoor escape. The area features stunning beaches and a lively boardwalk, where visitors can indulge in shopping and dining experiences. With its inviting esplanade and family-friendly beach areas, the Delaware Beaches provide the perfect backdrop for relaxation and fun. Whether you’re sunbathing on the sand or enjoying a seaside meal, this coastal gem is sure to enhance your holiday experience.
  • Bridgeville: Just 3.1km away from Greenwood, Bridgeville is a quaint city that offers a blend of outdoor activities and family-oriented attractions. Visitors can explore local boardwalks and recreation parks, providing a variety of options for entertainment and relaxation. The nearby national state park adds to the allure, offering stunning landscapes and opportunities for hiking and wildlife observation. With its charming atmosphere and accessible attractions, Bridgeville is an ideal spot for a delightful day out with loved ones.

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 a breeze

Are you eager to save on your upcoming getaway? Being flexible with your travel dates can make a real difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that aligns with your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient platform for you to plan new adventures, manage your existing arrangements, or review your bookings. Your saved or reserved properties are now conveniently categorised into Potential, Upcoming, or Current Trips. To explore the Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Explore the beachside setting in Greenwood

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

Activities and attractions in and around Greenwood

Are you looking for attractions to see during your stay? Venture out of your holiday home and experience everything that makes Greenwood a fun place to get away to. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city centre:

  • 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 fun outdoor activities or just want to take in the scenery, Greenwood is a great place to spend some time outside. Here are some of the area’s noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Travelling to and around Greenwood

The nearest airport is in Georgetown, DE (GED-Sussex County), located 14.7 mi (23.6 km) from the city centre. If you can't find a flight that's convenient for your trip, you could book a flight to Easton, MD (ESN-Easton - Newnam), which is 25.5 mi (41 km) away.

Frequently asked questions

How much does it cost to rent a holiday home in Greenwood?
Prices for holiday 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 holiday 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, Delaware, the best options are found in nearby coastal areas such as Rehoboth Beach and Dewey Beach. These towns offer a vibrant beach atmosphere and are just a short drive from Greenwood. Along the Rehoboth Beach boardwalk, you can find a variety of charming beach houses that provide easy access to the sandy shores and the lively beachfront scene. Many properties in this area come equipped with amenities such as outdoor decks, spacious living areas, and fully stocked kitchens, great for families or groups looking to enjoy seaside living.

In Dewey Beach, the atmosphere is more laid-back but equally inviting. Here, you can discover beach houses with features like private patios, outdoor showers, and proximity to both the beach and local nightlife. These rentals often cater to those seeking a more relaxed beach experience, offering amenities that enhance comfort and convenience.

Additionally, the nearby Cape Henlopen State Park presents opportunities for outdoor activities, including hiking and biking trails, along with beautiful natural beaches. Rentals in this area may offer scenic views and easy access to nature, with some properties featuring amenities like fire pits and picnic areas, ideal for enjoying the coastal environment.
What is the most popular type of holiday rental accomodation in Greenwood?
In Greenwood, holiday houses are the most popular type of holiday rental, with several available throughout the area. These homes typically feature spacious living areas, fully equipped kitchens, and outdoor spaces for enjoying the pleasant Delaware weather. Many are located in quiet neighbourhoods, providing a comfortable retreat for families or groups. Additionally, there are several mobile homes and cabins that offer unique accommodations, often set in more natural surroundings, ideal for those looking to connect with the outdoors.
Are there any family house rentals in Greenwood?
In Greenwood, Delaware, there are several family-friendly house rentals available, making it a suitable destination for those travelling with children. This charming area boasts homes with spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where kids can enjoy some fresh air. Many properties often include amenities such as Wi-Fi and central heating, ensuring a comfortable stay.

Visitors to Greenwood will find themselves in proximity to local parks, superb for family outings, as well as attractions like the nearby Delaware Agricultural Museum, which offers educational experiences for all ages.
Can I find long-stay holiday rentals in Greenwood?
A long-stay holiday rental in Greenwood is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any remote work holiday rentals in Greenwood?
In Greenwood, Delaware, there are several remote work-friendly holiday rentals available, making it a great choice for those looking to balance work and leisure. Travellers can expect properties that offer essential amenities such as high-speed internet and Wi-Fi access in the rooms, ensuring a seamless work experience. Many accommodations are designed for comfort, featuring spacious living areas and dedicated workspaces.

The town itself is located in a peaceful environment, ideal for those needing a tranquil setting to concentrate. Being close to local attractions and outdoor spaces, guests can enjoy breaks in nature, adding to the overall experience. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Greenwood holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Greenwood with parking available—perfect for families or travellers 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 holiday rental amenities include fully equipped kitchens, great for preparing meals during your stay. Many properties also feature porches or lanais, providing a lovely space to relax outdoors. Families travelling with young children will find rentals that offer travel cribs and children's books, ensuring a comfortable and enjoyable experience for all ages. Additionally, coffee and tea makers are commonly available, allowing guests to enjoy their favourite hot beverages at their convenience.
When is the best time to visit Greenwood for a holiday rental?
The best time to visit Greenwood for a holiday rental is during the summer months, particularly in July, when the area is alive with activity and warmth. This peak season, spanning from June to August, draws travellers, making it an ideal time for outdoor explorations and community events.

In July, temperatures in Greenwood typically range from 20 to 30 degrees Celsius, providing a pleasant climate for activities such as hiking, cycling, and enjoying the local parks. The atmosphere is vibrant, with plenty of opportunities to engage with fellow visitors and participate in various summer festivities.

For those seeking a more budget-friendly experience, consider planning your trip in December. While this month is part of the low season, it offers a unique charm with quieter surroundings, allowing for a peaceful escape and a chance to enjoy the winter landscape.
How early should I book a Greenwood holiday rental?
Book your Greenwood holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Greenwood?
In Greenwood, Delaware, visitors can explore several charming attractions that showcase the area's rich history and natural beauty. The town is known for its proximity to the picturesque Redden State Forest, offering opportunities for hiking, picnicking, and observing local wildlife. The forest features numerous trails that are ideal for outdoor enthusiasts.

Additionally, the nearby historic town of Milton, just a short drive away, boasts attractions such as the Milton Historical Society and the serene Broadkill River, superb for kayaking and fishing.
Can I change or cancel my Greenwood home rental booking on Vrbo?
To find Greenwood holiday 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 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 travellers 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 cosy cabin or a beach house, 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 holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, 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 organising 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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