Best Vacation Homes in Greenwood
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Cabin
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
AU $283/Night
For 7 Nights AU $1,981
1302.43 ft²
5 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Parking
- Internet
AU $309/Night
For 7 Nights AU $2,160
2 Guests
1 Bedroom
1 Bathroom
Couples Retreat
Cabin
- Fireplace/Heating
- Air Conditioner
- Internet
AU $283/Night
For 7 Nights AU $1,981
900 ft²
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $259/Night
For 7 Nights AU $1,810
279.86 ft²
12 Guests
6 Bedrooms
5 Bathrooms
Bed & Breakfast
- View
- Parking
- Air Conditioner
AU $325/Night
For 7 Nights AU $2,278
3 Guests
2 Bedrooms
1 Bathroom
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
AU $195/Night
For 7 Nights AU $1,361
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Kitchen
- Parking
AU $216/Night
For 7 Nights AU $1,511
4 Guests
1 Bedroom
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $213/Night
For 7 Nights AU $1,490
Greenwood Luxury Rentals
12 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Private Pool
- Hot Tub
- Fireplace/Heating
AU $1,063/Night
For 7 Nights AU $7,438
1991.32 ft²
12 Guests
1 Bedroom
3 Bathrooms
Free Cancellation
House
- Parking
- Child Friendly
- Sports/Activities
AU $788/Night
For 7 Nights AU $5,518
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $553/Night
For 7 Nights AU $3,873
8 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $521/Night
For 7 Nights AU $3,644
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $442/Night
For 7 Nights AU $3,095
1989 ft²
12 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $438/Night
For 7 Nights AU $3,065
780 ft²
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $392/Night
For 7 Nights AU $2,743
319.33 ft²
38 Guests
57 Bedrooms
1 Bathroom
Free Cancellation
Hotel
- Private Pool
- Pool
- Parking
AU $383/Night
For 7 Nights AU $2,679
Greenwood Pet Friendly Vacation Rentals
5 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Pet Friendly
- Kitchen
AU $248/Night
For 7 Nights AU $1,732
301.39 ft²
24 Guests
79 Bedrooms
1 Bathroom
Hotel
- Private Pool
- Oceanfront
- Fireplace/Heating
AU $176/Night
For 7 Nights AU $1,235
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Hot Tub
- Fireplace/Heating
- Pool
AU $347/Night
For 7 Nights AU $2,430
236.81 ft²
24 Guests
103 Bedrooms
1 Bathroom
Family Friendly
Hotel
- Balcony/Terrace
- Pet Friendly
- Parking
AU $166/Night
For 7 Nights AU $1,159
1500 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
AU $440/Night
For 7 Nights AU $3,082
6 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Condo
- Balcony/Terrace
- Pet Friendly
- Kitchen
AU $354/Night
For 7 Nights AU $2,477
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
AU $599/Night
For 7 Nights AU $4,190
6800 ft²
15 Guests
9 Bedrooms
7 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
AU $2,015/Night
For 7 Nights AU $14,103
Greenwood Large Vacation Homes
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Child Friendly
- Security/Safety
AU $481/Night
For 7 Nights AU $3,368
1989 ft²
12 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
AU $344/Night
For 7 Nights AU $2,409
Why Choose Rent By Owner for your Greenwood Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Greenwood
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit this destination allows you to enjoy the region's climate and local ambiance, ensuring your stay in Greenwood aligns perfectly with your vacation plans and preferences.
Peak Season Highlights
Summer (June to August)
During the peak summer months, you'll enjoy warm weather ideal for outdoor activities and exploring local attractions in the region. This is the busiest time for vacation rentals, so advanced booking is recommended to secure your perfect stay.
Average Temperature Daytime: 85°F - Nighttime: 65°F
Fall (September to November)
Autumn brings pleasant weather and vibrant foliage, making it a popular season to visit the area. The comfortable temperatures are perfect for sightseeing and enjoying the natural landscape, attracting many visitors during this time.
Average Temperature Daytime: 75°F - Nighttime: 55°F
Off-Season Highlights
Winter (December to February)
In the winter months, the region sees fewer visitors, providing a quieter experience for those seeking tranquility and lower rates on vacation rentals. Mild temperatures make it suitable for cozy stays and off-season exploration.
Average Temperature Daytime: 45°F - Nighttime: 30°F
Spring (March to May)
Early spring offers a peaceful retreat before the summer crowds arrive, with blooming landscapes adding charm to your visit. Booking this period allows for an affordable and relaxed getaway in this destination.
Average Temperature Daytime: 60°F - Nighttime: 40°F
Weekly Weather Forecast for Greenwood
How to Book Your Greenwood Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Greenwood
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy private outdoor seating areas perfect for relaxing and dining al fresco.
- Take advantage of spacious yards ideal for outdoor games and activities.
- Make use of a barbecue grill to host enjoyable cookouts with family and friends.
- Relax by a swimming pool or hot tub, if available, to refresh during warm days.
- Benefit from well-maintained gardens or landscaped spaces that enhance the outdoor experience.
- Utilize outdoor fire pits or fireplaces for cozy evenings under the stars.
- Access nearby walking trails or nature paths common in this region for outdoor exploration.
Top Attractions Around Greenwood
What attractions are nearby?
In this charming region, you can enjoy a variety of outdoor activities and local attractions that showcase the best of Greenwood’s nearby countryside and community events, making it an ideal destination for a relaxing and engaging getaway.
Family Activities
- Greenwood Nature Trail: Embark on a family-friendly hike along this scenic trail to enjoy the area's lush landscapes and local wildlife.
- Deep Branch Park: Spend quality time at this community park, perfect for picnics, playground fun, and outdoor games with your loved ones.
- Greenwood Historical Museum: Discover the region’s rich history through engaging exhibits that offer educational entertainment for children and adults alike.
- Local Farm Tours: Experience the area’s agricultural roots by visiting nearby farms, where your family can learn about farming practices and interact with farm animals.
Adult Activities
- Gunpowder State Park: Immerse yourself in nature by exploring scenic trails, picnicking areas, and outdoor activities within this popular park nearby.
- Rehoboth Bay Water Activities: Enjoy kayaking, paddleboarding, or fishing on the tranquil waters of Rehoboth Bay, offering a relaxing escape close to your stay.
- Greenwood Historical Society Museum: Discover local history and culture through engaging exhibits that provide insight into the area's rich heritage.
- Golf at The Rookery Golf Course: Tee off at this well-maintained golf course, ideal for adults seeking leisure and scenic views just a short drive away.
Other Places to Stay in Greenwood, DE
Farmington
Greenwood Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Local Seasons: Research the area's seasonal trends to optimize your visit and enjoy outdoor activities when the weather is at its best.
- Explore Nearby Nature Spots: Take advantage of the region’s natural beauty by visiting nearby parks and trails during your stay in Greenwood.
- Discover Local Events and Festivals: Check the local calendar for events that will enrich your experience and give you a taste of this destination's community spirit.
- Choose Comfortable, Well-Reviewed Vacation Rentals: Select accommodations with positive reviews to ensure a relaxing and memorable visit here, making the most of your time in this region.
Transportation Options
- Greenwood Transit Bus Service: This local bus system offers convenient connections within the area, making it easy to explore nearby attractions and amenities.
- Rental Cars: Numerous rental agencies in the region provide flexible transportation options for your stay, allowing you to navigate Greenwood and beyond at your own pace.
- Taxi and Rideshare Services: Taxis and rideshare companies operate here, offering quick and reliable transport for short trips around town or to neighboring destinations.
- Local Taxi Services: Independent taxi providers serve the area, providing a dependable way to reach your vacation rental or explore the local surroundings comfortably.
Local Customs Options
- Greetings and Hospitality: Visitors are warmly welcomed here, with locals valuing politeness and friendly interactions to foster a sense of community in the area.
- Festivals and Celebrations: Participating in local festivals that celebrate seasonal harvests and regional heritage offers an authentic experience of the region's customs.
- Respect for Nature: The community emphasizes environmental stewardship, encouraging visitors to enjoy outdoor activities responsibly and preserve the area's natural beauty.
- Dining Etiquette: Sharing meals at family-style gatherings is common, where good manners and appreciation for regional cuisine play a significant role in social interactions here.
Frequently Asked Questions About Greenwood?
1. What are the top vacation rentals in Greenwood?
There are a lot of options in Greenwood. If you plan on staying in the Greenwood area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Greenwood:
- Cozy cottage on the Miller farm.
- The Towers Bed & Breakfast
- Grandma's Cottage Milford Delaware
- Swartzentruber Cottage close to DE Turf & Beaches, also for traveling nurses!
- Guest suite in the woods with private entry
- Swartzentruber Homestead. Cozy cabin on our 5th generation family farm!
- Luxury Treehouse with Large Deck
- Tiny House in the Woods, sleeps 3, full bath, linens provided, keurig & k cups
- Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
- Sunlit Milford Townhome Less Than 2 Mi to Riverwalk!
2. How many vacation rentals have private pools in Greenwood?
There are 4 vacation rentals with private pools near Greenwood. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Greenwood are best for families?
If you are looking for a family-friendly vacation home in Greenwood, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Greenwood:
4. How many Rentbyowner vacation rentals are available in Greenwood?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 68 in the Greenwood area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Greenwood.
5. How do I find the cancellation policy for my chosen vacation rental in Greenwood, Delaware?
You can review the specific cancellation policy by checking the listing details on the booking platform. If you have any questions or need clarification, it’s best to contact the property owner directly before confirming your reservation.
6. What amenities should I expect when booking a vacation rental in this area?
The amenities vary by property, so it’s important to read the listing carefully. Common features include Wi-Fi, parking, and kitchen facilities. For additional amenities, reach out to the host for further details.
7. Are there any specific check-in and check-out times I should be aware of in Greenwood, Delaware?
Check-in and check-out times are typically listed on the property page. These times can differ between rentals, so reviewing the details or speaking with the property owner ensures a smooth arrival and departure.
8. What is the process if I need to modify or cancel my reservation in the region?
Modification and cancellation policies are outlined in the listing. For changes or cancellations, contact the property owner promptly through the platform to ensure proper handling according to their guidelines.
9. How do I ensure my stay complies with local regulations in this destination?
It’s advisable to verify any regional rules or restrictions with the property owner prior to booking. They can provide guidance on local regulations that might affect your stay.
Greenwood Top Rated Vacation Rentals
355.21 ft²
19 Guests
62 Bedrooms
1 Bathroom
Hotel
- Private Pool
- Fireplace/Heating
- Pool
AU $183/Night
For 7 Nights AU $1,278
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
AU $170/Night
For 7 Nights AU $1,187
AU $218/Night
For 7 Nights AU $1,524
AU $140/Night
For 7 Nights AU $984
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Pool
- Breakfast
- Kitchen
AU $156/Night
For 7 Nights AU $1,088
330.99 ft²
36 Guests
91 Bedrooms
8 Bathrooms
Ocean View
Hotel
- Oceanfront
- Fireplace/Heating
- Pool
AU $300/Night
For 7 Nights AU $2,097
298.7 ft²
24 Guests
77 Bedrooms
8 Bathrooms
Free Cancellation
Hotel
- Oceanfront
- Fireplace/Heating
- Pool
AU $229/Night
For 7 Nights AU $1,602
1 Bedroom
1 Bathroom
Family Friendly
Hotel
- Fireplace/Heating
- Pool
- Breakfast
AU $146/Night
For 7 Nights AU $1,019
